Dictionary of Contact Allergens: Chemical Structures, Sources, and References

Jean-Pierre Lepoittevin and Christophe J. Le Coz

Contents 1 Introduction ...... 21 2 Abietic Acid ...... 22 2.1 Suggested Reading ...... 22 3 Acetaldehyde ...... 22 3.1 Suggested Reading ...... 22 4 Acetophenone Azine ...... 22 4.1 Suggested Reading ...... 23 5 Acid Blue 158 ...... 23 5.1 Suggested Reading ...... 23 6 Acrylamide ...... 23 6.1 Suggested Reading ...... 23 7 Acrylates, Cyanoacrylate, and Methacrylates ...... 23 7.1 Acrylic Acid and Acrylates ...... 23 7.2 Bisphenol A Diglycidylether Diacrylate ...... 23 7.3 Bisphenol A Glycidyl Methacrylate ...... 24 7.4 1,4-Butanediol Diacrylate ...... 24 7.5 1,4-Butanediol Dimethacrylate ...... 24 7.6 n-Butyl Acrylate ...... 25 7.7 tert-Butyl Acrylate ...... 25 7.8 Cyanoacrylic Acid and Cyanoacrylates ...... 25 7.9 Diethyleneglycol Diacrylate ...... 25

J.-P. Lepoittevin (*) Laboratoire de Dermatochimie, University of Strasbourg, Strasbourg, France e-mail: [email protected] C. J. Le Coz Cabinet de Dermatologie, Strasbourg, France e-mail: [email protected]

© Springer Nature Switzerland AG 2019 1 J. D. Johansen et al. (eds.), Contact Dermatitis, https://doi.org/10.1007/978-3-319-72451-5_58-1 2 J.-P. Lepoittevin and C. J. Le Coz

7.10 Ethyl Acrylate ...... 26 7.11 Ethyl Cyanoacrylate ...... 26 7.12 Ethyleneglycol Dimethacrylate ...... 26 7.13 2-Ethylhexyl Acrylate ...... 27 7.14 Ethyl Methacrylate ...... 27 7.15 Glycidyl Methacrylate ...... 27 7.16 1,6-Hexanediol Diacrylate ...... 27 7.17 2-Hydroxyethyl Acrylate ...... 28 7.18 2-Hydroxyethyl Methacrylate ...... 28 7.19 2-Hydroxypropyl Acrylate ...... 28 7.20 2-Hydroxypropyl Methacrylate ...... 29 7.21 Isobornyl Acrylate (IBOA) ...... 29 7.22 Methacrylic Acid and Methacrylates ...... 29 7.23 Methyl Acrylate ...... 30 7.24 Methyl Methacrylate and Polymethyl Methacrylate ...... 30 7.25 Pentaerythritol Triacrylate ...... 30 7.26 Polyurethane Dimethacrylate ...... 31 7.27 Tetraethylene Glycol Dimethacrylate ...... 31 7.28 Triethyleneglycol Dimethacrylate ...... 32 7.29 Trimethylolpropane Triacrylate ...... 32 7.30 Tripropylene Glycol Diacrylate ...... 32 7.31 Urethane Acrylate ...... 33 8 Acrylonitrile ...... 33 8.1 Suggested Reading ...... 33 9 Alachlor® ...... 33 9.1 Suggested Reading ...... 33 10 Alantolactone ...... 34 10.1 Suggested Reading ...... 34 11 Alkyl (C12–C20) ...... 34 11.1 Suggested Reading ...... 34 12 Allicin ...... 34 12.1 Suggested Reading ...... 34 13 Allyl Glycidyl Ether ...... 35 13.1 Suggested Reading ...... 35 14 Allyl ...... 35 14.1 Suggested Reading ...... 35 15 Allyl Propyl Disulfide ...... 35 15.1 Suggested Reading ...... 35 16 Alprenolol ...... 35 16.1 Suggested Reading ...... 35 17 Amethocaine ...... 36 17.1 Suggested Reading ...... 36 18 p-Amino-N,N-Diethylaniline ...... 36 18.1 Suggested Reading ...... 36 19 4-Amino-3-Nitrophenol ...... 36 19.1 Suggested Reading ...... 36 20 p-Aminoazobenzene ...... 36 20.1 Suggested Reading ...... 37 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 3

21 p-Aminodiphenylamine (Hydrochloride) ...... 37 21.1 Suggested Reading ...... 37 22 Aminoethylethanolamine ...... 37 22.1 Suggested Reading ...... 37 23 o-Aminophenol ...... 37 23.1 Suggested Reading ...... 37 24 p-Aminophenol ...... 37 24.1 Suggested Reading ...... 38 25 Aminophylline ...... 38 25.1 Suggested Reading ...... 38 26 N,N-bis-(3-Aminopropyl) Dodecylamine ...... 38 26.1 Suggested Reading ...... 38 27 Ammonium Persulfate ...... 38 27.1 Suggested Reading ...... 39 28 Ammonium Thioglycolate ...... 39 28.1 Suggested Reading ...... 39 29 Amoxicillin ...... 39 29.1 Suggested Reading ...... 39 30 Ampicillin ...... 39 30.1 Suggested Reading ...... 40 31 Amprolium (Hydrochloride) ...... 40 31.1 Suggested Reading ...... 40 32 Amyl Cinnamyl ...... 40 32.1 Suggested Reading ...... 40 33 Amylcinnamaldehyde ...... 40 33.1 Suggested Reading ...... 40 34 Anacardic Acids ...... 41 34.1 Suggested Reading ...... 41 35 Anethole ...... 41 35.1 Suggested Reading ...... 41 36 Anisyl Alcohol ...... 41 36.1 Suggested Reading ...... 41 37 Antimony Trioxide ...... 41 37.1 Suggested Reading ...... 42 38 Arsenic and Arsenic Salts (Sodium Arsenate) ...... 42 38.1 Suggested Reading ...... 42 39 Articaine (Hydrochloride) ...... 42 39.1 Suggested Reading ...... 42 40 Atranol ...... 42 40.1 Suggested Reading ...... 42 41 Azaperone ...... 43 41.1 Suggested Reading ...... 43 42 Azathioprine ...... 43 42.1 Suggested Reading ...... 43 4 J.-P. Lepoittevin and C. J. Le Coz

43 Basic Red 22 ...... 43 43.1 Suggested Reading ...... 43 44 Basic Red 46 ...... 44 44.1 Suggested Reading ...... 44 45 Befunolol ...... 44 45.1 Suggested Reading ...... 44 46 Benomyl ...... 44 46.1 Suggested Reading ...... 44 47 Benzalkonium Chloride ...... 44 47.1 Suggested Reading ...... 45 48 (BIT) ...... 45 48.1 Suggested Reading ...... 45 49 ...... 45 49.1 Suggested Reading ...... 46 50 Benzoyl Peroxide ...... 46 50.1 Suggested Reading ...... 47 51 Benzydamine Hydrochloride ...... 47 51.1 Suggested Reading ...... 47 52 Benzyl Alcohol ...... 47 52.1 Suggested Reading ...... 47 53 Benzyl Benzoate ...... 47 53.1 Suggested Reading ...... 48 54 Benzyl Salicylate ...... 48 54.1 Suggested Reading ...... 48 55 Benzylpenicillin ...... 48 55.1 Suggested Reading ...... 48 56 BHA ...... 48 56.1 Suggested Reading ...... 49 57 BHT ...... 49 57.1 Suggested Reading ...... 49 58 Bioban® CS-1135 ...... 49 58.1 Suggested Reading ...... 49 59 Bioban® CS-1246 ...... 49 59.1 Suggested Reading ...... 49 60 Bioban® P-1487 ...... 50 60.1 Suggested Reading ...... 50 61 Bisphenol A ...... 50 61.1 Suggested Reading ...... 50 62 Bisphenol A Diglycidyl Ether (DGEBA) ...... 50 62.1 Suggested Reading ...... 51 63 o,p-Bisphenol F and p,p-Bisphenol F ...... 51 63.1 Suggested Reading ...... 51 64 Bisphenol F Diglycidyl Ether (DGEBF) ...... 51 64.1 Suggested Reading ...... 52 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 5

65 Brominated Epoxy Resin ...... 52 65.1 Suggested Reading ...... 52 66 1-Bromo-3-Chloro-5,5-Dimethylhydantoin ...... 52 66.1 Suggested Reading ...... 53 67 Bromohydroxyacetophenone ...... 53 67.1 Suggested Reading ...... 53 68 Bronopol ...... 53 68.1 Suggested Reading ...... 53 69 ...... 53 69.1 Suggested Reading ...... 54 70 Bufexamac ...... 54 70.1 Suggested Reading ...... 54 71 Buprenorphine ...... 55 71.1 Suggested Reading ...... 55 72 1,4-Butanediol Diglycidyl Ether ...... 55 72.1 Suggested Reading ...... 55 73 N-Butyl-1,2-Benzisothiazolin-3-one (BBIT) ...... 55 73.1 Suggested Reading ...... 55 74 N-tert-Butyl-bis-(2-Benzothiazole) Sulfenamide ...... 56 74.1 Suggested Reading ...... 56 75 Butyl Carbitol ...... 56 75.1 Suggested Reading ...... 56 76 p-tert-Butylcatechol ...... 56 76.1 Suggested Reading ...... 56 77 n-Butyl Glycidyl Ether ...... 56 77.1 Suggested Reading ...... 57 78 tert-Butylhydroquinone ...... 57 78.1 Suggested Reading ...... 57 79 p-tert-Butyl-alpha-methylhydrocinnamic Aldehyde ...... 57 79.1 Suggested Reading ...... 57 80 Butylene Glycol ...... 57 80.1 Suggested Reading ...... 58 81 Para-tert-Butylphenol ...... 58 81.1 Suggested Reading ...... 58 82 Caffeic Acid Dimethyl Allylic Ester ...... 58 82.1 Suggested Reading ...... 58 83 Caprylhydroxamic Acid ...... 59 83.1 Suggested Reading ...... 59 84 Captafol ...... 59 84.1 Suggested Reading ...... 59 85 Captan ...... 59 85.1 Suggested Reading ...... 59 86 ...... 60 86.1 Suggested Reading ...... 60 6 J.-P. Lepoittevin and C. J. Le Coz

87 Carbodiimide ...... 60 87.1 Suggested Reading ...... 60 88 ...... 60 88.1 Suggested Reading ...... 60 89 Cardols ...... 60 89.1 Suggested Reading ...... 61 90 Δ-3-Carene ...... 61 90.1 Suggested Reading ...... 61 91 Carteolol ...... 61 91.1 Suggested Reading ...... 61 92 CD1 ...... 61 92.1 Suggested Reading ...... 62 93 CD2 ...... 62 93.1 Suggested Reading ...... 62 94 CD3 ...... 62 94.1 Suggested Reading ...... 62 95 CD4 ...... 63 95.1 Suggested Reading ...... 63 96 CD6 ...... 63 96.1 Suggested Reading ...... 63 97 Cefaclor ...... 63 97.1 Suggested Reading ...... 64 98 Cephalosporins ...... 64 98.1 Suggested Reading ...... 64 99 Cetearyl Isononanoate ...... 64 99.1 Suggested Reading ...... 65 100 Chloramphenicol ...... 65 100.1 Suggested Reading ...... 65 101 Chlorhexidine (Digluconate) ...... 65 101.1 Suggested Reading ...... 65 102 5-Chloro-1-Methyl-4-Nitroimidazole ...... 65 102.1 Suggested Reading ...... 66 103 Chloroacetamide ...... 66 103.1 Suggested Reading ...... 66 104 Chloroacetophenone ...... 66 104.1 Suggested Reading ...... 66 105 Chloroatranol ...... 66 105.1 Suggested Reading ...... 66 106 Chlorocresol ...... 67 106.1 Suggested Reading ...... 67 107 Chlorophorin ...... 67 107.1 Suggested Reading ...... 67 108 Chlorothalonil ...... 67 108.1 Suggested Reading ...... 67 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 7

109 Chlorpromazine ...... 68 109.1 Suggested Reading ...... 68 110 Cinnamal ...... 68 110.1 Suggested Reading ...... 68 111 Cinnamyl Alcohol ...... 68 111.1 Suggested Reading ...... 68 112 Citral ...... 69 112.1 Suggested Reading ...... 69 113 Citronellol ...... 69 113.1 Suggested Reading ...... 69 114 Clindamycin ...... 69 114.1 Suggested Reading ...... 70 115 Clopidol ...... 70 115.1 Suggested Reading ...... 70 116 Cloxacillin ...... 70 116.1 Suggested Reading ...... 70 117 Cobalt Naphthenate ...... 70 117.1 Suggested Reading ...... 71 118 Cocamidopropyl Betaine ...... 71 118.1 Suggested Reading ...... 71 119 Cocamidopropyl Dimethylamine ...... 71 119.1 Suggested Reading ...... 71 120 Coconut Diethanolamide ...... 71 120.1 Suggested Reading ...... 72 121 Codeine (Phosphate, Hydrochloride) ...... 72 121.1 Suggested Reading ...... 72 122 Costunolide ...... 72 122.1 Suggested Reading ...... 73 123 Coumarin ...... 73 123.1 Suggested Reading ...... 73 124 Cresyl Glycidyl Ether ...... 73 124.1 Suggested Reading ...... 73 125 Cyclohexanone ...... 73 125.1 Suggested Reading ...... 74 126 2-Cyclohexen-1-one ...... 74 126.1 Suggested Reading ...... 74 127 N-Cyclohexyl-2-Benzothiazylsulfenamide ...... 74 127.1 Suggested Reading ...... 74 128 N-Cyclohexyl-N-Phenyl-p-Phenylenediamine ...... 74 128.1 Suggested Reading ...... 75 129 N-(Cyclohexylthio)phthalimide ...... 75 129.1 Suggested Reading ...... 75 130 Cymene ...... 75 130.1 Suggested Reading ...... 75 8 J.-P. Lepoittevin and C. J. Le Coz

131 Cymoxanil ...... 75 131.1 Suggested Reading ...... 76 132 Dazomet ...... 76 132.1 Suggested Reading ...... 76 133 DDT ...... 76 133.1 Suggested Reading ...... 76 134 Decyl ...... 76 134.1 Suggested Reading ...... 76 135 Dehydrocostuslactone ...... 77 135.1 Suggested Reading ...... 77 136 Deoxylapachol ...... 77 136.1 Suggested Reading ...... 77 137 Diallyl Disulfide ...... 77 137.1 Suggested Reading ...... 77 138 Diaminodiphenylmethane ...... 77 138.1 Suggested Reading ...... 78 139 Diammonium Hydrogen Phosphate ...... 78 139.1 Suggested Reading ...... 78 140 Diazodiethylaniline Chloride ...... 78 140.1 Suggested Reading ...... 78 141 Diazolidinyl Urea ...... 79 141.1 Suggested Reading ...... 79 142 Dibenzothiazyl Disulfide ...... 79 142.1 Suggested Reading ...... 79 143 Dibucaine (Hydrochloride) ...... 79 143.1 Suggested Reading ...... 79 144 Dibutyl Phthalate ...... 80 144.1 Suggested Reading ...... 80 145 Dibutylthiourea ...... 80 145.1 Suggested Reading ...... 80 146 4,5-Dichloro-2-N-Octyl-4-Isothiazolin-3-one ...... 80 146.1 Suggested Reading ...... 80 147 1,3-Dichloropropene ...... 81 147.1 Suggested Reading ...... 81 148 ...... 81 148.1 Suggested Reading ...... 81 149 N,N-Dicyclohexyl-2-Benzothiazole Sulfenamide ...... 81 149.1 Suggested Reading ...... 81 150 Dicyclohexyl Carbodiimide ...... 81 150.1 Suggested Reading ...... 81 151 Didecyldimethylammonium Chloride ...... 82 151.1 Suggested Reading ...... 82 152 Diethanolamine ...... 82 152.1 Suggested Reading ...... 82 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 9

153 Diethyl Sebacate ...... 82 153.1 Suggested Reading ...... 82 154 Diethyleneglycol Diglycidyl Ether ...... 82 154.1 Suggested Reading ...... 83 155 Diethylenetriamine ...... 83 155.1 Suggested Reading ...... 83 156 Diethyl Phthalate ...... 83 156.1 Suggested Reading ...... 83 157 Diethylthiourea ...... 83 157.1 Suggested Reading ...... 83 158 N-N0-Diglycidylaniline (DGA) ...... 84 158.1 Suggested Reading ...... 84 159 Diisopropyl Carbodiimide ...... 84 159.1 Suggested Reading ...... 84 160 Diisopropylbenzothiazyl-2-Sulfenamide ...... 84 160.1 Suggested Reading ...... 84 161 2,5-Dimercapto-1,3,4-Thiadiazole ...... 84 161.1 Suggested Reading ...... 85 162 ...... 85 162.1 Suggested Reading ...... 85 163 Dimethoxon ...... 85 163.1 Suggested Reading ...... 85 164 2,6-Dimethoxy-1,4-Benzoquinone ...... 85 164.1 Suggested Reading ...... 85 165 (R)-3,4-Dimethoxy-Dalbergione ...... 86 165.1 Suggested Reading ...... 86 166 (S)-4,40-Dimethoxy Dalbergione ...... 86 166.1 Suggested Reading ...... 86 167 5,8-Dimethoxypsoralen ...... 86 167.1 Suggested Reading ...... 86 168 Dimethyl Phthalate ...... 86 168.1 Suggested Reading ...... 87 169 4-N,N-(Dimethylamino) Benzenediazonium Chloride ...... 87 169.1 Suggested Reading ...... 87 170 3-Dimethylaminopropylamine ...... 87 170.1 Suggested Reading ...... 87 171 Dimethyldiphenylthiuram Disulfide ...... 87 171.1 Suggested Reading ...... 87 172 Dimethylformamide ...... 88 172.1 Suggested Reading ...... 88 173 Dimethyl Fumarate ...... 88 173.1 Suggested Reading ...... 88 174 2,4-Dimethylol Phenol ...... 88 174.1 Suggested Reading ...... 88 10 J.-P. Lepoittevin and C. J. Le Coz

175 2,6-Dimethylol Phenol ...... 89 175.1 Suggested Reading ...... 89 176 Dimethylthiocarbamyl Benzothiazole Sulfide ...... 89 176.1 Suggested Reading ...... 89 177 Dimethylthiourea ...... 89 177.1 Suggested Reading ...... 89 178 Dinitrochlorobenzene ...... 89 178.1 Suggested Reading ...... 90 179 Dinitrofluorobenzene ...... 90 179.1 Suggested Reading ...... 90 180 2,4-Dinitrotoluene ...... 90 180.1 Suggested Reading ...... 90 181 Dipentamethylenethiuram Disulfide ...... 90 181.1 Suggested Reading ...... 91 182 Dipentamethylenethiuram Hexasulfide ...... 91 182.1 Suggested Reading ...... 91 183 Dipentamethylenethiuram Tetrasulfide ...... 91 183.1 Suggested Reading ...... 91 184 Dipentene ...... 91 184.1 Suggested Reading ...... 91 185 Diphencyprone ...... 92 185.1 Suggested Reading ...... 92 186 Diphenhydramine (Hydrochloride) ...... 92 186.1 Suggested Reading ...... 92 187 N,N0-Diphenyl-4-Phenylenediamine ...... 92 187.1 Suggested Reading ...... 92 188 1,3-Diphenylguanidine ...... 93 188.1 Suggested Reading ...... 93 189 4,40-Diphenylmethane Diisocyanate ...... 93 189.1 Suggested Reading ...... 93 190 Diphenylthiourea ...... 93 190.1 Suggested Reading ...... 93 191 Disperse Blue 106 ...... 94 191.1 Suggested Reading ...... 94 192 Disperse Blue 124 ...... 94 192.1 Suggested Reading ...... 94 193 Disperse Orange 3 ...... 94 193.1 Suggested Reading ...... 95 194 Disperse Orange 31 ...... 95 194.1 Suggested Reading ...... 95 195 Disperse Red 11 ...... 95 195.1 Suggested Reading ...... 96 196 Disperse Yellow 3 ...... 96 196.1 Suggested Reading ...... 96 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 11

197 Dithianone ...... 96 197.1 Suggested Reading ...... 96 198 Dodecyl Gallate ...... 96 198.1 Suggested Reading ...... 96 199 Doxepin ...... 97 199.1 Suggested Reading ...... 97 200 Drometrizole ...... 97 200.1 Suggested Reading ...... 97 201 Epichlorhydrin ...... 97 201.1 Suggested Reading ...... 97 202 Epoxy Resins of the Bisphenol A Type ...... 98 202.1 Suggested Reading ...... 98 203 (2,3-Epoxypropyl)trimethylammonium Chloride ...... 98 203.1 Suggested Reading ...... 98 204 Estradiol ...... 99 204.1 Suggested Reading ...... 99 205 Ethoxyquin ...... 99 205.1 Suggested Reading ...... 99 206 Ethyl Alcohol ...... 99 206.1 Suggested Reading ...... 99 207 4-Ethylpyridine ...... 99 207.1 Suggested Reading ...... 100 208 Ethylbutylthiourea ...... 100 208.1 Suggested Reading ...... 100 209 Ethylene Oxide ...... 100 209.1 Suggested Reading ...... 100 210 Ethylenediamine ...... 100 210.1 Suggested Reading ...... 101 211 Ethylenethiourea ...... 101 211.1 Suggested Reading ...... 101 212 Ethylhexylglycerin ...... 101 212.1 Suggested Reading ...... 101 213 Eugenol ...... 101 213.1 Suggested Reading ...... 102 214 Euxyl®K 400 (See 1,2-Dibromo-2,4-Dicyanobutane and Phenoxyethanol) ...... 102 214.1 Suggested Reading ...... 102 215 Famotidine ...... 102 215.1 Suggested Reading ...... 102 216 Farnesol ...... 102 216.1 Suggested Reading ...... 102 217 Fenvalerate ...... 103 217.1 Suggested Reading ...... 103 218 Fluazinam ...... 103 218.1 Suggested Reading ...... 103 12 J.-P. Lepoittevin and C. J. Le Coz

219 Flutamide ...... 103 219.1 Suggested Reading ...... 103 220 Folpet ...... 103 220.1 Suggested Reading ...... 104 221 Formaldehyde ...... 104 221.1 Suggested Reading ...... 104 222 Frullanolide ...... 104 222.1 Suggested Reading ...... 105 223 Furaltadone ...... 105 223.1 Suggested Reading ...... 105 224 Furazolidone ...... 105 224.1 Suggested Reading ...... 105 225 Geraniol ...... 105 225.1 Suggested Reading ...... 106 226 Glutaraldehyde ...... 106 226.1 Suggested Reading ...... 106 227 Glyceryl Thioglycolate ...... 106 227.1 Suggested Reading ...... 106 228 Glycidyl 1-Naphthyl Ether ...... 106 228.1 Suggested Reading ...... 107 229 3-Glycidyloxypropyltrime-thoxysilane ...... 107 229.1 Suggested Reading ...... 107 230 Grotan BK ...... 107 230.1 Suggested Reading ...... 107 231 HC Blue No. 7 ...... 107 231.1 Suggested Reading ...... 108 232 HC Yellow No. 7 ...... 108 232.1 Suggested Reading ...... 108 233 Hexamethylene Diisocyanate ...... 108 233.1 Suggested Reading ...... 108 234 Hexamidine ...... 108 234.1 Suggested Reading ...... 108 235 Hexanediol Diglycidyl Ether ...... 109 235.1 Suggested Reading ...... 109 236 Hexyl Cinnamic Aldehyde ...... 109 236.1 Suggested Reading ...... 109 237 Hydralazine ...... 109 237.1 Suggested Reading ...... 109 238 Hydrangenol ...... 109 238.1 Suggested Reading ...... 110 239 Hydrazine ...... 110 239.1 Suggested Reading ...... 110 240 ...... 110 240.1 Suggested Reading ...... 110 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 13

241 Hydrocortisone 17-Butyrate ...... 110 241.1 Suggested Reading ...... 111 242 Hydrogen Peroxide ...... 111 242.1 Suggested Reading ...... 111 243 ...... 111 243.1 Suggested Reading ...... 111 244 (S)-4-Hydroxy-4-Methoxydalbergione ...... 111 244.1 Suggested Reading ...... 112 245 Hydroxycitronellal ...... 112 245.1 Suggested Reading ...... 112 246 Hydroxylamine and Hydroxylammonium Salts ...... 112 246.1 Suggested Reading ...... 112 247 Hydroxymethylpentacyclo- hexenecarboxaldehyde ...... 112 247.1 Suggested Reading ...... 113 248 Hypochlorous Acid and Hypochlorites ...... 113 248.1 Suggested Reading ...... 113 249 Imidazolidinyl Urea ...... 113 249.1 Suggested Reading ...... 113 250 Iodopropynyl Butylcarbamate ...... 114 250.1 Suggested Reading ...... 114 251 Isoeugenol ...... 114 251.1 Suggested Reading ...... 114 252 Alpha-Isomethylionone ...... 114 252.1 Suggested Reading ...... 115 253 Isophorone Diamine ...... 115 253.1 Suggested Reading ...... 115 254 Isopropyl Myristate ...... 115 254.1 Suggested Reading ...... 115 255 N-Isopropyl-N-Phenyl-4-Phenylenediamine ...... 115 255.1 Suggested Reading ...... 116 256 Ketoprofen ...... 116 256.1 Suggested Reading ...... 116 257 Labetalol ...... 116 257.1 Suggested Reading ...... 116 258 Lactucin ...... 116 258.1 Suggested Reading ...... 117 259 Lactucopicrin ...... 117 259.1 Suggested Reading ...... 117 260 Lapachenol ...... 117 260.1 Suggested Reading ...... 117 261 Lapachol ...... 117 261.1 Suggested Reading ...... 118 262 Lawsone ...... 118 262.1 Suggested Reading ...... 118 14 J.-P. Lepoittevin and C. J. Le Coz

263 Lidocaine ...... 118 263.1 Suggested Reading ...... 118 264 Lilial® ...... 119 265 Limonene ...... 119 265.1 Suggested Reading ...... 119 266 Linalool ...... 119 266.1 Suggested Reading ...... 119 267 Linalyl Acetate ...... 120 267.1 Suggested Reading ...... 120 268 Lincomycin (Hydrochloride Monohydrate) ...... 120 268.1 Suggested Reading ...... 120 269 Lindane ...... 120 269.1 Suggested Reading ...... 120 270 Lyral® ...... 120 271 ...... 120 271.1 Suggested Reading ...... 121 272 Mancozeb ...... 121 272.1 Suggested Reading ...... 121 273 Maneb ...... 121 273.1 Suggested Reading ...... 121 274 Melamine and Melamine-Formaldehyde Resins ...... 122 274.1 Suggested Reading ...... 122 275 Mercaptobenzothiazole ...... 122 275.1 Suggested Reading ...... 122 276 Mercaptobenzothiazole Salts ...... 122 276.1 Suggested Reading ...... 123 277 MESNA ...... 123 277.1 Suggested Reading ...... 123 278 Metacresol ...... 123 278.1 Suggested Reading ...... 123 279 Metanil Yellow ...... 123 279.1 Suggested Reading ...... 123 280 Methenamine ...... 123 280.1 Suggested Reading ...... 124 281 ...... 124 281.1 Suggested Reading ...... 124 282 ...... 124 282.1 Suggested Reading ...... 124 283 ...... 124 283.1 Suggested Reading ...... 125 284 (R)-4-Methoxy Dalbergione ...... 125 284.1 Suggested Reading ...... 125 285 Methoxy PEG-17/Dodecyl Glycol Copolymer ...... 125 285.1 Suggested Reading ...... 125 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 15

286 Methoxypsoralens ...... 125 286.1 Suggested Reading ...... 126 287 Methyl Aminolevulinate ...... 126 287.1 Suggested Reading ...... 126 288 Methyl-2,3-Epoxy-3-(4-Methoxyphenyl)Propionate ...... 126 288.1 Suggested Reading ...... 126 289 Methyl Gallate ...... 126 289.1 Suggested Reading ...... 127 290 Methyl Heptine Carbonate ...... 127 290.1 Suggested Reading ...... 127 291 Methyl Octine Carbonate ...... 127 291.1 Suggested Reading ...... 127 292 Methyl Salicylate ...... 127 292.1 Suggested Reading ...... 127 293 Methyl-Terpyridine ...... 128 293.1 Suggested Reading ...... 128 294 2-Methyl-4,5-Trimethylene-4-Isothiazolin-3-one ...... 128 294.1 Suggested Reading ...... 128 295 Methylchloroisothiazolinone ...... 128 295.1 Suggested Reading ...... 128 296 Methylchloroisothiazolinone + Methylsiothiazolinone (MCI/MI) ...... 128 296.1 Suggested Reading ...... 129 297 Methyldibromoglutaronitrile ...... 129 297.1 Suggested Reading ...... 129 298 Methylhexahydrophthalic Anhydride ...... 129 298.1 Suggested Reading ...... 130 299 Methylisothiazolinone ...... 130 299.1 Suggested Reading ...... 130 300 Methylol Phenols ...... 130 300.1 Suggested Reading ...... 130 301 1-Methylpyrrolidone ...... 130 301.1 Suggested Reading ...... 131 302 Metol (Sulfate) ...... 131 302.1 Suggested Reading ...... 131 303 Metronidazole (Hydrochloride) ...... 131 303.1 Suggested Reading ...... 131 304 ...... 132 304.1 Suggested Reading ...... 132 305 Mezlocilin ...... 132 305.1 Suggested Reading ...... 132 306 Monoethanolamine ...... 132 306.1 Suggested Reading ...... 132 307 Morphine (Morphine Hydrochloride, Morphine Tartrate) ...... 132 307.1 Suggested Reading ...... 133 16 J.-P. Lepoittevin and C. J. Le Coz

308 4-Morpholinyl-2-Benzothiazyle Disulfide ...... 133 308.1 Suggested Reading ...... 133 309 Morpholinyl Mercaptobenzothiazole ...... 133 309.1 Suggested Reading ...... 133 310 ...... 133 310.1 Suggested Reading ...... 134 311 1-Naphthol ...... 134 311.1 Suggested Reading ...... 134 312 Naphthol AS ...... 134 312.1 Suggested Reading ...... 134 313 Neomycin (Neomycin B Hydrochloride, Neomycin B Sulfate) ...... 134 313.1 Suggested Reading ...... 135 314 Nicotine ...... 135 314.1 Suggested Reading ...... 135 315 3-Nitro-4-hydroxyethylaminophenol ...... 135 315.1 Suggested Reading ...... 136 316 2-Nitro-4-Phenylenediamine ...... 136 316.1 Suggested Reading ...... 136 317 Nitrofurazone ...... 136 317.1 Suggested Reading ...... 136 318 Nitroglycerin ...... 136 318.1 Suggested Reading ...... 137 319 Nonoxynols ...... 137 319.1 Suggested Reading ...... 137 320 ...... 137 320.1 Suggested Reading ...... 137 321 Octyl Gallate ...... 138 321.1 Suggested Reading ...... 138 322 2-N-Octyl-4-isothiazolin-3-one ...... 138 322.1 Suggested Reading ...... 138 323 Olaquindox ...... 138 323.1 Suggested Reading ...... 139 324 Omeprazole ...... 139 324.1 Suggested Reading ...... 139 325 Oxacillin ...... 139 325.1 Suggested Reading ...... 139 326 7-Oxodehydroabietic Acid ...... 139 326.1 Suggested Reading ...... 140 327 Oxprenolol ...... 140 327.1 Suggested Reading ...... 140 328 Pantothenol ...... 140 328.1 Suggested Reading ...... 140 329 Parabens (Parahydroxybenzoic Acid Esters) ...... 140 329.1 Suggested Reading ...... 141 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 17

330 p-Phenylenediamine ...... 141 330.1 Suggested Reading ...... 142 331 Paraquat (Dichloride, Methosulfate) ...... 142 331.1 Suggested Reading ...... 142 332 ...... 142 332.1 Suggested Reading ...... 143 333 Parthenolide ...... 143 333.1 Suggested Reading ...... 143 334 Penicillins ...... 143 334.1 Suggested Reading ...... 143 335 Pentachloronitrobenzene ...... 143 335.1 Suggested Reading ...... 144 336 Pentadecylcatechol ...... 144 336.1 Suggested Reading ...... 144 337 Phenoxyethanol ...... 144 337.1 Suggested Reading ...... 144 338 Phenyl Glycidyl Ether ...... 144 338.1 Suggested Reading ...... 145 339 Phenyl-Alpha-Naphthylamine ...... 145 339.1 Suggested Reading ...... 145 340 Phenyl-beta-naphthylamine ...... 145 340.1 Suggested Reading ...... 145 341 Phenylephrine (Hydrochloride) ...... 145 341.1 Suggested Reading ...... 146 342 Phenylethyl Caffeate ...... 146 342.1 Suggested Reading ...... 146 343 Phthalic Anhydride ...... 146 343.1 Suggested Reading ...... 146 344 Picric Acid ...... 146 344.1 Suggested Reading ...... 147 345 Alpha-Pinene ...... 147 345.1 Suggested Reading ...... 147 346 Beta-pinene ...... 147 346.1 Suggested Reading ...... 147 347 Piperazine ...... 147 347.1 Suggested Reading ...... 147 348 Piroxicam ...... 148 348.1 Suggested Reading ...... 148 349 Pivampicillin ...... 148 349.1 Suggested Reading ...... 148 350 Polyaminopropyl Biguanide ...... 148 350.1 Suggested Reading ...... 149 351 Polymyxin B (Sulfate) ...... 149 351.1 Suggested Reading ...... 149 18 J.-P. Lepoittevin and C. J. Le Coz

352 Potassium Metabisulfite ...... 149 352.1 Suggested Reading ...... 149 353 Povidone-Iodine ...... 150 353.1 Suggested Reading ...... 150 354 Prilocaine (Hydrochloride) ...... 150 354.1 Suggested Reading ...... 150 355 Primin ...... 150 355.1 Suggested Reading ...... 150 356 Pristinamycin ...... 150 356.1 Suggested Reading ...... 151 357 Procaine (Hydrochloride) ...... 151 357.1 Suggested Reading ...... 151 358 Propacetamol ...... 151 358.1 Suggested Reading ...... 152 359 Propargite ...... 152 359.1 Suggested Reading ...... 152 360 Propranolol ...... 152 360.1 Suggested Reading ...... 152 361 Propyl Gallate ...... 153 361.1 Suggested Reading ...... 153 362 Propylene Glycol ...... 153 362.1 Suggested Reading ...... 153 363 Propylene Oxide ...... 153 363.1 Suggested Reading ...... 153 364 Pseudoephedrine ...... 154 364.1 Suggested Reading ...... 154 365 Pyrethroids ...... 154 365.1 Suggested Reading ...... 154 366 Pyrethrosin ...... 154 366.1 Suggested Reading ...... 155 367 Pyridine ...... 155 367.1 Suggested Reading ...... 155 368 Pyrithione ...... 155 368.1 Suggested Reading ...... 156 369 ...... 156 369.1 Suggested Reading ...... 156 370 PVP ...... 156 370.1 Suggested Reading ...... 156 371 PVP/Eicosene Copolymer ...... 157 371.1 Suggested Reading ...... 157 372 PVP/Hexadecene Copolymer ...... 157 372.1 Suggested Reading ...... 157 373 Quaternium-15 ...... 157 373.1 Suggested Reading ...... 158 374 Quaternium-22 ...... 158 374.1 Suggested Reading ...... 158 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 19

375 Ranitidine ...... 158 375.1 Suggested Reading ...... 158 376 Resorcinol ...... 158 376.1 Suggested Reading ...... 159 377 Silane ...... 159 377.1 Suggested Reading ...... 159 378 Sodium Bisulfite ...... 159 378.1 Suggested Reading ...... 159 379 Sodium Lauryl Sulfate ...... 159 379.1 Suggested Reading ...... 160 380 Sodium Metabisulfite ...... 160 380.1 Suggested Reading ...... 160 381 Sodium Methyldithiocarbamate ...... 160 381.1 Suggested Reading ...... 160 382 Sodium Sulfite ...... 160 382.1 Suggested Reading ...... 161 383 Solvent Red 23 ...... 161 383.1 Suggested Reading ...... 161 384 Sorbitan Sesquioleate ...... 161 384.1 Suggested Reading ...... 161 385 Spectinomycin ...... 161 385.1 Suggested Reading ...... 162 386 Tetrabenzylthiuram Disulfide ...... 162 386.1 Suggested Reading ...... 162 387 Tetrabutylthiuram Disulfide ...... 162 387.1 Suggested Reading ...... 162 388 Tetrabutylthiuram Monosulfide ...... 162 388.1 Suggested Reading ...... 162 389 Tetrachloroacetophenone ...... 162 389.1 Suggested Reading ...... 163 390 Tetraethylthiuram Disulfide ...... 163 390.1 Suggested Reading ...... 163 391 Tetraethylthiuram Monosulfide ...... 163 391.1 Suggested Reading ...... 163 392 Tetraglycidyl-4,40-methylenedianiline (TGMDA) ...... 163 392.1 Suggested Reading ...... 164 393 Tetraisobutylthiuram Disulfide ...... 164 393.1 Suggested Reading ...... 164 394 Tetramethylthiuram Disulfide ...... 164 394.1 Suggested Reading ...... 164 395 Tetramethylthiuram Monosulfide ...... 165 395.1 Suggested Reading ...... 165 396 Tetrazepam ...... 165 396.1 Suggested Reading ...... 165 397 Thebaine ...... 165 397.1 Suggested Reading ...... 166 20 J.-P. Lepoittevin and C. J. Le Coz

398 Thiabendazole ...... 166 398.1 Suggested Reading ...... 166 399 Thimerosal ...... 166 399.1 Suggested Reading ...... 166 400 Thioctic Acid ...... 166 400.1 Suggested Reading ...... 167 401 Thiourea ...... 167 401.1 Suggested Reading ...... 167 402 Thymoquinone ...... 167 402.1 Suggested Reading ...... 167 403 Timolol ...... 167 403.1 Suggested Reading ...... 167 404 Pivalate ...... 168 404.1 Suggested Reading ...... 168 405 Tocopherol, Tocopheryl Acetate (DL-, D-) ...... 168 405.1 Suggested Reading ...... 168 406 Toluene-2,5-Diamine ...... 169 406.1 Suggested Reading ...... 169 407 Toluene Diisocyanate ...... 169 407.1 Suggested Reading ...... 169 408 Tosyl Chloride ...... 169 408.1 Suggested Reading ...... 169 409 Triacetin ...... 170 409.1 Suggested Reading ...... 170 410 Tribenoside ...... 170 410.1 Suggested Reading ...... 170 411 Tributyltin Oxide ...... 170 411.1 Suggested Reading ...... 170 412 Trichloroethane ...... 170 412.1 Suggested Reading ...... 171 413 Trichloroethylene ...... 171 413.1 Suggested Reading ...... 171 414 Triethanolamine ...... 171 414.1 Suggested Reading ...... 171 415 Triethylenetetramine ...... 171 415.1 Suggested Reading ...... 171 416 Triforine ...... 172 416.1 Suggested Reading ...... 172 417 Triglycidyl-p-Aminophenol (TGPAP) ...... 172 417.1 Suggested Reading ...... 172 418 Triglycidyl Isocyanurate ...... 172 418.1 Suggested Reading ...... 173 419 N-[3-(Trimethoxysilyl)propyl]-N-(vinylbenzyl)ethylenediamine Monohydrochloride ...... 173 419.1 Suggested Reading ...... 173 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 21

420 N-(3-Trimethoxysilylpropyl)-Ethylenediamine ...... 173 420.1 Suggested Reading ...... 173 421 2,4,6-Trimethylol Phenol ...... 173 421.1 Suggested Reading ...... 174 422 Trimethylthiourea ...... 174 422.1 Suggested Reading ...... 174 423 Tulipalin A and Tulipalin B ...... 174 423.1 Suggested Reading ...... 174 424 Tuliposide A ...... 174 424.1 Suggested Reading ...... 174 425 Tylosin ...... 175 425.1 Suggested Reading ...... 175 426 Urushiol ...... 175 426.1 Suggested Reading ...... 175 427 Usnic Acid (d-Usnic Acid, l-Usnic Acid) ...... 176 427.1 Suggested Reading ...... 176 428 Vinylpyridine ...... 176 428.1 Suggested Reading ...... 176 429 Virginiamycin ...... 176 429.1 Suggested Reading ...... 177 430 Zinc bis-Dibutyldithiocarbamate ...... 177 430.1 Suggested Reading ...... 177 431 Zinc bis-Diethyldithiocarbamate ...... 177 431.1 Suggested Reading ...... 177 432 Zinc bis-Dimethyldithiocarbamate ...... 178 432.1 Suggested Reading ...... 178 433 Zinc Ethylene-bis-dithiocarbamate ...... 178 433.1 Suggested Reading ...... 178 434 Zinc Propylenebis(dithiocarbamate) ...... 178 434.1 Suggested Reading ...... 178

Abstract have been omitted since they were obsolete, This chapter has been written in order to famil- extremely rarely implicated in contact derma- iarize the reader with the chemical structure of titis, their case reports were too imprecise, or chemicals implicated in contact dermatitis, they are extensively treated in other chapters of mainly as haptens responsible for allergic con- the textbook. tact dermatitis. For each molecule, the princi- pal name is used for classification. We have also listed the most important synonym(s), the 1 Introduction Chemical Abstract Service (CAS) Registry Number that characterizes the substance and This chapter has been written in order to familiar- its chemical structure. The reader will find one ize the reader with the chemical structure of or more relevant literature references. As it is chemicals implicated in contact dermatitis, mainly not possible to be exhaustive, some allergens as haptens responsible for allergic contact 22 J.-P. Lepoittevin and C. J. Le Coz dermatitis. For each molecule, the principal name Karlberg AT (2017) Oxidation products and the is used for classification. We have also listed the skin – the effect of hydroperoxides. Contact most important synonym(s), the Chemical Dermatitis 76:63–66 Abstract Service (CAS) Registry Number, which characterizes the substance and its chemical struc- ture. The reader will find one or more relevant 3 Acetaldehyde literature references. As it was not possible to be exhaustive, some allergens have been omitted Acetic Aldehyde, Ethanal, Ethylic Aldehyde since they were obsolete, extremely rarely impli- CAS Registry Number [75-07-0] cated in contact dermatitis, their case reports were too imprecise, or they are extensively treated in O other chapters of the textbook. From a practical chemical point of view, acrylates, cyanoacrylates H and (meth)acrylates, cephalosporins, and para- bens have been grouped together. Acetaldehyde, as its metabolite, is responsible for many of the effects of , such as hepatic or neurological toxicity. A case of contact allergy 2 Abietic Acid was reported in the textile industry, where dimethoxane was used as a biocide agent in tex- CAS Registry Number [514-10-3] tiles, and its degradation led to acetaldehyde. Abietic acid is probably the major allergen of colophony or , along with dehydroabietic acid, by way of air oxidation. The formation of 3.1 Suggested Reading highly sensitizing hydroperoxides has been dem- onstrated, and therefore the detection of abietic Eriksson CJ (2001) The role of acetaldehyde in acid in a material indicates that allergenic compo- the actions of alcohol (update 2000). Alcohol nents of colophony are present. Clin Exp Res 25(suppl 5):15S–32S Shmunes E, Kempton RJ (1980) Allergic contact dermatitis to dimethoxane in a spin finish. Contact Dermatitis 6:421–424

4 Acetophenone Azine

Methylphenyl Ketazine CAS Registry Number [729-43-1] COOH Acetophenone azine has been shown to be responsible of severe allergic contact dermatitis to shin pads. It was present in EVA foam. Cases 2.1 Suggested Reading were also reported to shoes. Karlberg AT, Bohlinder K, Boman A et al (1988) Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony. J Pharm Pharmacol 40:42–47 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 23

4.1 Suggested Reading O

Raison-Peyron N, Bergendorff O, Bourrain J-L NH et al (2016) Acetophenone azine: a new aller- 2 gen responsible for severe contact dermatitis from shin pads. Contact Dermatitis – 75:106 110 6.1 Suggested Reading De Fré C, Bergendorff O, Raison-Peyron N et al (2017) Acetophenone azine: a new shoe aller- Aalto-Korte K, Jolanki R, Suuronen K et al (2002) gen causing severe foot dermatitis. Contact Biochemist’s occupational allergic contact der- – Dermatitis 76:416 417 matitis from iodoacetamide and acrylamide. Contact Dermatitis 47:361–364 Beyer DJ, Belsito DV (2000) Allergic contact 5 Acid Blue 158 dermatitis from acrylamide in a chemical mixer. Contact Dermatitis 42:181–182 CAS Registry Numbers [6370-08-7], [39389-99- 6], and [53126-96-8] This azo dye has the Color Index nr. 14880. It 7 Acrylates, Cyanoacrylate, is found in suture materials. and Methacrylates

OH NaO3S 7.1 Acrylic Acid and Acrylates OH SO3Na N CAS Registry Number [79-10-7] N Acrylates are esters from acrylic acid. Occupa- tional contact allergies from acrylates have fre- quently been reported and mainly concern workers exposed to the glues based on acrylic 5.1 Suggested Reading acid, as well as dental workers and beauticians.

Hausen BM (2003) Allergic contact dermatitis O O from colored surgical suture material: contact allergy to epsilon-caprolactam and acid blue OH OR 158. Am J Contact Dermat 14:174–175 Raap U, Wieczorek D, Kapp A et al (2008) Aller- gic contact dermatitis to acid blue 158 in suture Acrylic acid Acrylate material. Contact Dermatitis 59:192–193

7.2 Bisphenol A Diglycidylether 6 Acrylamide Diacrylate

CAS Registry Number [79-06-1] 2,2-bis[4-(2-Hydroxy-3-acryloxypropoxy)phenyl]- Acrylamide is used in the plastic polymers propane (Bis-GA) industry for water treatments and soil stabilization CAS Registry Number [8687-94-9] and to prepare polyacrylamide gels for electro- Bis-GA is an epoxy diacrylate. It caused con- phoresis. This neurotoxic, carcinogenic, and tact dermatitis in a process worker, being genotoxic substance is known to have caused contained in -light-curable acrylic contact dermatitis in industrial and laboratory paints. workers. 24 J.-P. Lepoittevin and C. J. Le Coz

7.4 1,4-Butanediol Diacrylate

O O CAS Registry Number [1070-70-8] O O O O A positive patch test was observed in a male OH OH process worker in a paint factory, sensitized to an epoxy diacrylate contained in raw materials of ultraviolet-light-curable paint. The positive reac- tion was probably due to a cross-reactivity. 7.2.1 Suggested Reading Aalto-Korte K, Jungewelter S, Henriks-Eckerman O ML et al (2009) Contact allergy to epoxy O (meth)acrylates. Contact Dermatitis 61:9–21 O Jolanki R, Kanerva L, Estlander T (1995) Occu- O pational allergic contact dermatitis caused by epoxy diacrylate in ultraviolet-light-cured paint, and bisphenol A in dental composite resin. Contact Dermatitis 33:94–99 7.4.1 Suggested Reading Jolanki R, Kanerva L, Estlander T (1995) Occu- pational allergic contact dermatitis caused by 7.3 Bisphenol A Glycidyl epoxy diacrylate in ultraviolet-light-cured Methacrylate paint, and bisphenol A in dental composite resin. Contact Dermatitis 33:94–99 Bis-GMA CAS Registry Number [1565-94-2] Bis-GMA is an epoxy methacrylate. Sensitiza- 7.5 1,4-Butanediol Dimethacrylate tion occurs in dentists, beauticians, and con- sumers with sculptured photopolymerizable nails. CAS Registry Number [2082-81-7] Sensitization to 1,4-butanediol dimethacrylate was reported in dental technicians, with cross- O O reactivity to methyl methacrylate.

O O O O O OH OH O O

7.3.1 Suggested Reading O Aalto-Korte K, Jungewelter S, Henriks-Eckerman ML et al (2009) Contact allergy to epoxy 7.5.1 Suggested Reading (meth)acrylates. Contact Dermatitis 61:9–21 Rustemeyer T, Frosch PJ (1996) Occupational Kanerva L, Estlander T, Jolanki R (1989) Allergic skin diseases in dental laboratory technicians. contact dermatitis from dental composite (I). Clinical picture and causative factors. Con- – resins due to aromatic epoxy acrylates and tact Dermatitis 34:125 133 aliphatic acrylates. Contact Dermatitis 20:201–211 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 25

7.6 n-Butyl Acrylate caused by exposure to acrylates during work with dental prostheses. Contact Dermatitis CAS Registry Number [141-32-2] 28:268–275 Sensitization to n-butyl acrylate can occur in the dental profession. 7.8 Cyanoacrylic Acid O and Cyanoacrylates

O 2-Cyanoacrylic Acid CAS Registry Number [15802-18-3] Cyanoacrylates, particularly 2-ethyl cyanoac- rylate, are derived from cyanoacrylic acid. They 7.6.1 Suggested Reading are used as sealants. Daecke C, Schaller J, Goos M (1994) Acrylates as potent allergens in occupational and domestic O O – N exposures. Contact Dermatitis 30:190 191 NC Kanerva L, Estlander T, Jolanki R et al (1993) OH OR Occupational allergic contact dermatitis caused by exposure to acrylates during work with dental prostheses. Contact Dermatitis Cyanoacrylic acid Cyanoacrylate 28:268–275 Rustemeyer T, Frosch PJ (1996) Occupational skin diseases in dental laboratory technicians. 7.8.1 Suggested Reading (I). Clinical picture and causative factors. Con- Fischer AA (1985) Reactions to cyanoacrylate tact Dermatitis 34:125–133 adhesives: “instant glue”. Cutis 35:18; 20; 22 Tarvainen K (1995) Analysis of patients with allergic patch test reactions to a plastics and 7.7 tert-Butyl Acrylate glue series. Contact Dermatitis 32:346–351

CAS Registry Number [1663-39-4] Sensitization may affect dental workers. 7.9 Diethyleneglycol Diacrylate

O CAS Registry Number [4074-88-8] Diethyleneglycol diacrylate was positive in a O painter sensitized to his own acrylate-based paint.

o o o o o 7.7.1 Suggested Reading Kanerva L, Estlander T, Jolanki R et al (1993) Occupational allergic contact dermatitis 26 J.-P. Lepoittevin and C. J. Le Coz

7.9.1 Suggested Reading Beauticians are exposed to contact dermatitis Nakamura M, Arima Y, Yoneda K et al (1999) from nail glues. Occupational contact dermatitis from acrylic monomer in paint. Contact Dermatitis O 40:228–229 NC O 7.10 Ethyl Acrylate 7.11.1 Suggested Reading CAS Registry Number [140-88-5] Bruze M, Björkner B, Lepoittevin JP (1995) Ethyl acrylate is a sensitizer in the dental pro- Occupational allergic contact dermatitis from fession. ethyl cyanoacrylate. Contact Dermatitis – o 32:156 159 Fitzgerald DA, Bhaggoe R, English JSC (1995) o Contact sensitivity to cyanoacrylate nail- adhesive with dermatitis at remote sites. Con- tact Dermatitis 32:175–176 Tomb R, Lepoittevin JP, Durepaire F et al (1993) 7.10.1 Suggested Reading Ectopic contact dermatitis from ethyl cyanoac- Kanerva L, Estlander T, Jolanki R et al (1993) rylate instant adhesives. Contact Dermatitis Occupational allergic contact dermatitis 28:206–208 caused by exposure to acrylates during work with dental prostheses. Contact Dermatitis 28:268–275 7.12 Ethyleneglycol Dimethacrylate Rustemeyer T, Frosch PJ (1996) Occupational skin diseases in dental laboratory technicians. CAS Registry Number [97-90-5] (I). Clinical picture and causative factors. Con- Ethyleneglycol dimethacrylate (EGDMA) is a tact Dermatitis 34:125–133 cross-linking agent of acrylic resins and is employed to optimize the dilution of high- viscosity monomers and to link together the mac- romolecules constituting the polymer. It caused 7.11 Ethyl Cyanoacrylate contact dermatitis in dental technicians and dental assistants. A case was also reported in a manufac- Ethyl-2-cyanoacrylate turer of car rear-view mirrors. CAS Registry Number [7085-85-0] Ethyl cyanoacrylate is contained in instant O glues for metal, glass, rubber, plastics, textiles, tissues, and nails. It polymerizes almost instanta- O neously in air at room temperature and bonds O immediately and strongly to surface keratin. O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 27

7.12.1 Suggested Reading 7.14.1 Suggested Reading Farli M, Gasperini M, Francalanci S et al (1990) Kanerva L, Lauerma A, Estlander T et al (1996) Occupational contact dermatitis in 2 dental Occupational allergic contact dermatitis technicians. Contact Dermatitis 22:282–287 caused by photobonded sculptured nails and a Kanerva L, Jolanki R, Estlander T (1995) Occu- review of (meth) acrylates in nail cosmetics. pational allergic contact dermatitis from Am J Contact Dermat 7:109–115 2-hydroxyethyl methacrylate and ethylene gly- Rustemeyer T, Frosch PJ (1996) Occupational col dimethacrylate in a modified acrylic struc- skin diseases in dental laboratory technicians. tural adhesive. Contact Dermatitis 35:84–89 (I). Clinical picture and causative factors. Con- Tosti A, Rapacchiale S, Piraccini BM et al (1991) tact Dermatitis 34:125–133 Occupational airborne contact dermatitis due to dimethacrylate. Contact Dermatitis 24:152–153 7.15 Glycidyl Methacrylate

CAS Registry Number [106-91-2] 7.13 2-Ethylhexyl Acrylate Glycidyl methacrylate, an epoxy methacrylate, was reported as the allergenic component of the 2-EHA anaerobic sealant Sta-Lok. CAS Registry Number [1322-13-0] O 2-EHA was contained in a surgical tape and caused allergic contact dermatitis in a patient. O O O

O 7.15.1 Suggested Reading Aalto-Korte K, Jungewelter S, Henriks-Eckerman 7.13.1 Suggested Reading ML et al (2009) Contact allergy to epoxy Daecke C, Schaller J, Goos M (1994) Acrylates as (meth)acrylates. Contact Dermatitis 61:9–21 potent allergens in occupational and domestic Dempsey KJ (1982) Hypersensitivity to Sta-Lok exposures. Contact Dermatitis 30:190–191 and Loctite anaerobic sealants. J Am Acad Dermatol 7:779–784

7.14 Ethyl Methacrylate 7.16 1,6-Hexanediol Diacrylate CAS Registry Number [97-63-2] Ethyl methacrylate is used in dental prostheses Hexamethylene Diacrylate or photobonded sculptured nails. CAS Registry Number [13048-33-4] Sensitization occurred after accidental occupa- O tional exposure in an employee in the laboratory of a plastic paint factory.

O 28 J.-P. Lepoittevin and C. J. Le Coz

O 7.18 2-Hydroxyethyl Methacrylate

O O 2-HEMA CAS Registry Number [868-77-9] O Sensitization to 2-HEMA concerns mainly dental technicians and dentists but can also occur 7.16.1 Suggested Reading in other workers such as printers, beauticians, or Botella-Estrada R, Mora E, de La Cuadra J (1992) consumers using photopolymerizable sculptured Hexanediol diacrylate sensitization after acci- nails. dental occupational exposure. Contact Derma- – titis 26:50 51 O

OH 7.17 2-Hydroxyethyl Acrylate O

2-HEA, Ethylene Glycol Acrylate CAS Registry Number [818-61-1] 7.18.1 Suggested Reading 2-HEA is contained in Lowicryl 4KM and Andersen SL, Rastogi SC, Andersen KE (2009) K11 M resins. It caused contact dermatitis in Occupational allergic contact dermatitis to workers embedding media for electron micros- hydroxyethyl methacrylate (2-HEMA) in a – copy. It may also be contained in UV-cured nail manicurist. Contact Dermatitis 61:48 50 gel used for photobonded, sculptured nails. Geukens S, Goossens A (2001) Occupational con- tact allergy to (meth)acrylates. Contact Derma- O titis 44:153–159 Kanerva L, Jolanki R, Estlander T (1995) Occu- OH O pational allergic contact dermatitis from 2-hydroxyethyl methacrylate and ethylene gly- col dimethacrylate in a modified acrylic struc- tural adhesive. Contact Dermatitis 35:84–89 7.17.1 Suggested Reading Kanerva L, Lauerma A, Estlander T et al (1996) 7.19 2-Hydroxypropyl Acrylate Occupational allergic contact dermatitis caused by photobonded sculptured nails and a CAS Registry Number [999-61-1] review of (meth) acrylates in nail cosmetics. A case of occupational contact dermatitis was – Am J Contact Dermat 7:109 115 reported in industry. Tobler M, Wüthrich B, Freiburghaus AU (1990) Contact dermatitis from acrylate and methac- O rylate compounds in Lowicryl® embedding media for electron microscopy. Contact Der- OH O matitis 23:96–102 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 29

7.19.1 Suggested Reading SL mix present in the baseline series even if not explained. Lovell CR, Rycroft RJG, Williams DMJ et al (1985) Contact dermatitis from the irritancy (immediate and delayed) and allergenicity of hydroxypropyl acrylate. Contact Dermatitis 12:117–118

7.21.1 Suggested Reading 7.20 2-Hydroxypropyl Methacrylate Christoffers WA, Coenraads, P-J, Schuttelaar, M-L (2013) Two decades of occupational CAS Registry Number [27813-02-1] (meth)acrylate patch test results and focus on Sensitization to 2-hydroxypropyl methacrylate isobornyl acrylate. Contact Dermatitis concerns mainly the dental profession. 69:86–92 Herman A, Aerts O, Baeck M et al (2017) Allergic O contact dermatitis caused by isobornyl acrylate in Freestyle Libre, a newly introduced glucose O sensor. Contact Dermatitis 77:367–373

OH Raison-Peyron N, Mowitz M, Bonardel N et al (2018) Allergic contact dermatitis caused by isobornyl acrylate in OmniPod, an innovative tubeless insulin pump. Contact Dermatitis 7.20.1 Suggested Reading 79:76–80 Kanerva L, Estlander T, Jolanki R et al (1993) Occupational allergic contact dermatitis caused by exposure to acrylates during work 7.22 Methacrylic Acid with dental prostheses. Contact Dermatitis and Methacrylates 28:268–275 Kanerva L, Estlander T, Jolanki R (1997) Occu- CAS Registry Number [79-41-4] pational allergic contact dermatitis caused by Methacrylates are derived from methacrylic triacrylic tri-cure glass ionomer. Contact Der- acid. They are used in the production of a great matitis 37:49 variety of polymers. As they are moderate to Rustemeyer T, Frosch PJ (1996) Occupational strong sensitizers, sensitization concerns many skin diseases in dental laboratory technicians. professions. Dental technicians, assistants, and (I). Clinical picture and causative factors. Con- surgeons are frequently exposed. Methacrylates tact Dermatitis 34:125–133 were reported as occupational allergens in chem- ically cured or photocured sculptured nails. 7.21 Isobornyl Acrylate (IBOA) O O Acrylic Acid Isobornyl Ester, IBA CAS Registry Number [5888-33-5] OH OR Isobornyl acrylate has been identified as the main sensitizer in innovative devices such as glu- Methacrylic acid Methacrylate cose sensors and insulin pumps. Frequent con- comitant reactions have been reported with the 30 J.-P. Lepoittevin and C. J. Le Coz

7.23 Methyl Acrylate O

MA O CAS Registry Number [96-33-3] MA is contained in some nail lacquers. 7.24.1 Suggested Reading O Gebhardt M, Geier J (1996) Evaluation of patch test results with denture material series. Con- O tact Dermatitis 34:191–195 Kanerva L, Estlander T, Jolanki R et al (1993) Occupational allergic contact dermatitis caused by exposure to acrylates during work 7.23.1 Suggested Reading with dental prostheses. Contact Dermatitis Kanerva L, Estlander T, Jolanki R et al (1993) 28:268–275 Occupational allergic contact dermatitis Kanerva L, Lauerma A, Estlander T et al (1996) caused by exposure to acrylates during work Occupational allergic contact dermatitis with dental prostheses. Contact Dermatitis caused by photobonded sculptured nails and a 28:268–275 review of (meth) acrylates in nail cosmetics. Kanerva L, Lauerma A, Estlander T et al (1996) Am J Contact Dermat 7:109–115 Occupational allergic contact dermatitis Kiec-Swierczynska MK (1996) Occupational caused by photobonded sculptured nails and a allergic contact dermatitis due to acrylates in review of (meth) acrylates in nail cosmetics. Lodz. Contact Dermatitis 34:419–422 Am J Contact Dermat 7:109–115

7.25 Pentaerythritol Triacrylate 7.24 Methyl Methacrylate and Polymethyl Methacrylate CAS Registry Numbers [3524-68-3] and others Pentaerythritol triacrylate is a multifunctional CAS Registry Numbers [80-62-6] and [9011-14-7] acrylic monomer. It can be contained in photo- Methyl methacrylate is one of the most com- polymerizable printer’s ink or varnishes. Sensiti- mon methacrylates. This acrylic monomer, the zation was described in dental technicians and in a essential component of the fluid mixed with the textile fabric printer. powder, causes allergic contact dermatitis mainly in dental technicians and dentists. Cases were also reported following the use of sculptured nails and ceramic workers. Polymethyl methacrylate is the O O O O result of polymerized methyl methacrylate mono- mers, which are used as sheets, molding, extru- sion powders, surface coating resins, emulsion HO O polymers, fibers, inks, and films. This material is also used in tooth implants, bone cements, and O hard corneal contact lenses. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 31

7.25.1 Suggested Reading 7.26.1 Suggested Reading Geukens S, Goossens A (2001) Occupational con- Dempsey KJ (1982) Hypersensitivity to Sta-Lok tact allergy to (meth)acrylates. Contact Derma- and Loctite anaerobic sealants. J Am Acad titis 44:153–159 Dermatol 7:779–784 Kanerva L, Estlander T, Jolanki R et al (1995) Occupational allergic contact dermatitis and contact urticaria caused by polyfunctional 7.27 Tetraethylene Glycol aziridine hardener. Contact Dermatitis Dimethacrylate 33:304–309 Rustemeyer T, Frosch PJ (1996) Occupational CAS Registry Number [109-17-1] skin diseases in dental laboratory technicians. Tetraethylene glycol dimethacrylate is a cross- (I). Clinical picture and causative factors. Con- linking agent of acrylic resins, employed to opti- tact Dermatitis 34:125–133 mize the dilution of high-viscosity monomers and to link together the macromolecules constituting the polymer, to make the three-dimensional struc- 7.26 Polyurethane Dimethacrylate ture more rigid. Occupational dermatitis was reported in a dental technician. The polyurethane dimethacrylate was contained in Loctite glues of the 300 and 500 series. O O O O O O H H O O O O N N O O R O 7.27.1 Suggested Reading O O Farli M, Gasperini M, Francalanci S et al (1990) Occupational contact dermatitis in 2 dental R = or technicians. Contact Dermatitis 22:282–287

O O H H

R O N N O O N N O R

H H O O

R = O OOO

O

O 32 J.-P. Lepoittevin and C. J. Le Coz

7.28 Triethyleneglycol O Dimethacrylate

O O CAS Registry Number [109-16-0] Triethyleneglycol dimethacrylate (TREGDMA) is a cross-linking agent of acrylic O resins, used in sealants or dental bonding resins. It is mainly used in dentistry by dental technicians O and dentists. O

O O 7.29.1 Suggested Reading O O Kanerva L, Estlander T, Jolanki R et al (1995) O Occupational allergic contact dermatitis and contact urticaria caused by polyfunctional 7.28.1 Suggested Reading aziridine hardener. Contact Dermatitis Kanerva L, Lauerma A, Estlander T et al (1996) 33:304–309 Occupational allergic contact dermatitis Kiec-Swierczynska MK (1996) Occupational caused by photobonded sculptured nails and a allergic contact dermatitis due to acrylates in review of (meth) acrylates in nail cosmetics. Lodz. Contact Dermatitis 34:419–422 – Am J Contact Dermat 7:109 115 Maurice PDL, Rycroft RJG (1986) Allergic con- Kiec-Swierczynska MK (1996) Occupational tact dermatitis from UV curing acrylate in the allergic contact dermatitis due to acrylates in manufacture of optical fibers. Contact Derma- – Lodz. Contact Dermatitis 34:419 422 titis 15:92–93 Rustemeyer T, Frosch PJ (1996) Occupational skin diseases in dental laboratory technicians. (I). Clinical picture and causative factors. Con- 7.30 Tripropylene Glycol Diacrylate tact Dermatitis 34:125–133 CAS Registry Number [42978-66-5] As a cause of occupational contact dermatitis, 7.29 Trimethylolpropane Triacrylate tripropylene glycol diacrylate was contained in dental resins, UV-cured inks, and nail cosmetics. CAS Registry Number [15625-89-5] Trimethylolpropane triacrylate (TMPTA) is a multifunctional acrylic monomer. It reacts with O O O O propyleneimine to form polyfunctional aziridine. Sensitization was observed in a textile fabric O O printer. Patch tests were positive with the poly- functional aziridine hardener but were negative to 7.30.1 Suggested Reading TMPTA. TMPTA caused contact dermatitis in an Kanerva L, Estlander T, Jolanki R et al (1993) optic fiber manufacturing worker and was Occupational allergic contact dermatitis reported as a sensitizer in a floor top coat or in caused by exposure to acrylates during work photopolymerizable inks. with dental prostheses. Contact Dermatitis 28:268–275 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 33

Kanerva L, Lauerma A, Estlander T et al (1996) CN Occupational allergic contact dermatitis caused by photobonded sculptured nails and a review of (meth) acrylates in nail cosmetics. Am J Contact Dermat 7:109–115 8.1 Suggested Reading

7.31 Urethane Acrylate Bakker JG, Jongen SMJ, Van Neer FCJ et al (1991) Occupational contact dermatitis due to Urethane acrylate gave a positive reaction in a acrylonitrile. Contact Dermatitis 24:50–53 lottery-ticket-coating machine worker sensitized Chu CY, Sun CC (2001) Allergic contact derma- to epoxy acrylate oligomers contained in a UV titis from acrylonitrile. Am J Contact Dermat varnish. 12:113–114

7.31.1 Suggested Reading ® Guimaraens D, Gonzalez MA, del Rio E et al 9 Alachlor (1994) Occupational airborne allergic contact dermatitis in the national mint and fiscal-stamp 2-Chloro-2,6-diethyl-N-(methoxymethyl)acetanilide, factory. Contact Dermatitis 30:172–173 2-Chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl) Kanerva L, Estlander T, Jolanki R et al (1993) acetamide Occupational allergic contact dermatitis CAS Registry Number [15972-60-8] ® caused by exposure to acrylates during work Alachlor is an herbicide. Occupational con- with dental prostheses. Contact Dermatitis tact dermatitis was rarely observed in agricultural 28:268–275 workers.

8 Acrylonitrile O

2-Propenenitrile N CH2Cl CAS Registry Number [107-13-1]

Acrylonitrile is a raw material used extensively O in industry, mainly for acrylic and modacrylic fibers, acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins, adiponitrile used in nylon’s synthesis, for nitrile rubber, and plastics. It is also used as an insecticide. This very toxic 9.1 Suggested Reading and irritant substance is also a sensitizer and caused both irritant and allergic contact dermatitis Won JH, Ahn SK, Kim SC (1993) Allergic contact in a production manufacturer. dermatitis from the herbicide Alachlor®. Con- tact Dermatitis 28:38–39 34 J.-P. Lepoittevin and C. J. Le Coz

10 Alantolactone C12,C14, and C16 fatty alcohols. Such variations explain uncertainty when searching for the precise CAS Registry Number [546-43-0] CAS Registry Number. Because alkyl glucosides The allergen eudesmanolide sesquiterpene lac- are comparable mixtures, patients sensitive to one tone was isolated from elecampane (Inula alkyl glucoside may also react to others. See helenium L.). With dehydrocostuslactone and Decyl Glucoside. costunolide, it is a component of the (sesquiter- pene) lactone mix used to detect sensitization to Compositae-Asteraceae.

O O

11.1 Suggested Reading

Goossens A, Decraene T, Platteaux N et al (2003) Glucosides as unexpected allergens in cos- 10.1 Suggested Reading metics. Contact Dermatitis 48:164–166 Le Coz CJ, Meyer MT (2003) Contact allergy to Ducombs G, Benezra C, Talaga P et al (1990) decyl glucoside in antiseptic after body pierc- Patch testing with the “sesquiterpene lactone ing. Contact Dermatitis 48:279–280 mix”: a marker for contact allergy to Compositae and other sesquiterpene-lactone- containing plants. Contact Dermatitis 12 Allicin 22:249–252 Lamminpää A, Estlander T, Jolanki R et al (1996) CAS Registry Number [539-86-6] Occupational allergic contact dermatitis Allicin is one of the major allergens in garlic caused by decorative plants. Contact Dermati- (Allium sativum L.). It is responsible for the char- tis 34:330–335 acteristic flavor of the bulbs and has immunomo- Kuno Y, Kawabe Y, Sakakibara S (1999) Allergic dulating and antibacterial properties. contact dermatitis associated with photosensi- tivity from alantolactone in a chrysanthemum S farmer. Contact Dermatitis 40:224–225 S

O 11 Alkyl Glucosides (C12–C20) 12.1 Suggested Reading Alkyl glucosides are copolymers; based on a fatty alcohol and a glucoside polymer, they comprise Bruynzeel DP (1997) Bulb dermatitis. Dermato- decyl glucoside, coco glucoside and lauryl (dode- logical problems in the flower bulb industries. cyl) glucoside in cosmetics, and cetearyl gluco- Contact Dermatitis 37:70–77 side as a surfactant and emulsifying agent because Lamminpää A, Estlander T, Jolanki R et al (1996) of its higher viscosity. Due to their manufacturing Occupational allergic contact dermatitis processes, they are blends of several copolymers. caused by decorative plants. Contact Dermati- For example, coco glucoside contains C6,C8,C10, tis 34:330–335 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 35

13 Allyl Glycidyl Ether 14.1 Suggested Reading

CAS Registry Number [106-92-3] Lerbaek A, Chandra Rastogi S, Menné T (2004) Allyl glycidyl ether is a monoglycidyl deriva- Allergic contact dermatitis from allyl isothio- tive, used as a reactive epoxy diluent for epoxy cyanate in a Danish cohort of 259 selected resins. As an impurity, it was considered to be the patients. Contact Dermatitis 51:79–83 sensitizing agent in a plastic industry worker aller- gic to 3-glycidyloxypropyl trimethoxysilane, an epoxy silane compound used as a fixing additive 15 Allyl Propyl Disulfide in silicone and polyurethane. CAS Registry Number [2179-59-1] O With allicin and diallyl sulfide, allyl propyl O disulfide is one of the allergens in garlic (Allium sativum L.).

13.1 Suggested Reading S S Aalto-Korte K, Pesonen M, Suuronen K (2015) Occupational allergic contact dermatitis 15.1 Suggested Reading caused by epoxy chemicals: occupations, sen- sitizing products and diagnosis. Contact Der- Bruynzeel DP (1997) Bulb dermatitis. Dermato- matitis 73:336–342 logical problems in the flower bulb industries. Angelini G, Rigano L, Foti C et al (1996) Occu- Contact Dermatitis 37:70–77 pational sensitization to epoxy resin and reac- tive diluents in marble workers. Contact – Dermatitis 35:11 16 16 Alprenolol Dooms-Goossens A, Bruze M, Buysse L et al (1995) Contact allergy to allyl glycidyl ether CAS Registry Number [13655-52-2] present as an impurity in Occupational cases of contact dermatitis due to 3-glycidyloxypropyltrimethoxysilane, a fixing this beta-blocker were reported in the pharmaceu- additive in silicone and polyurethane. Contact tical industry. Dermatitis 33:17–19

14

O N CAS Registry Number [57-06-7] H Allyl isothiocyanate is generated by enzymatic OH hydrolysis of the glucoside sinigrin, present in Cruciferae-, mainly the oil from black seed (Brassica nigra Koch). It may 16.1 Suggested Reading induce irritant and sometimes allergic contact der- matitis, mimicking the “tulip finger” dermatitis. Ekenvall L, Forsbeck M (1978) Contact eczema produced by α-adrenergic blocking agent (Alprenolol). Contact Dermatitis 4:190–194 36 J.-P. Lepoittevin and C. J. Le Coz

17 Amethocaine 18.1 Suggested Reading

Pantocaine, Tetracaine Aguirre A, Landa N, Gonzalez M et al (1992) CAS Registry Number [136-47-0] Allergic contact dermatitis in a photographer. Amethocaine is a local anesthetic used in den- Contact Dermatitis 27:340–341 tal surgery. It was reported as an agent of contact dermatitis in dentists or dental nurses and in ophthalmologists. 19 4-Amino-3-Nitrophenol

O 3-Nitro-4-aminophenol

N CAS Registry Number [610-81-1] O This hair dye used for semipermanent colors seems to be a rare sensitizer. HCI N OH H

17.1 Suggested Reading

NO2 Condé-Salazar L, Llinas MG, Guimaraens D et al (1988) Occupational allergic contact dermatitis NH2 from amethocaine. Contact Dermatitis 19:69–70 Opstrup MS, Sørensen HB, Zachariae C (2017) 19.1 Suggested Reading Occupational allergic contact dermatitis caused by tetracaine in an otorhinolaryngolo- Sánchez-Pérez J, García del Río I, Alvares Ruiz S, gist. Contact Dermatitis 76:55–57 et al (2004) Allergic contact dermatitis from direct dyes for hair coloration in hairdressers’ clients. Contact Dermatitis 50:261–262 18 p-Amino-N,N-Diethylaniline Søsted H, Menné T (2005) Allergy to 3-notro-p- Sulfate hydroxyethylaminophenol and 4-amino-3- nitrophenol in a hair dye. Contact Dermatitis 1,4-Benzenediamine, N,N-Diethyl-para-phenyl- 52:317–319 enediamine sulfate CAS Registry Number [6065-27-6] This color developer can induce sensitization 20 p-Aminoazobenzene in photographers. Solvent Yellow 1, C.I. 11000, Solvent Blue 7 CAS Registry Number [60-09-3] NH2 This azoic coloring can be reduced in para- phenylenediamine (PPD). It can be found in some N semipermanent hair dyes, and patch tests are fre- H2SO4 quently positive (about 30%) in hairdressers with hand dermatitis. Because of hydrolysis of the azo bond, the detection of sensitization to p- aminoazobenzene may be assumed by a PPD test. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 37

NH2 contact and airborne contact dermatitis in workers in the electronic industry or cable jointers.

N N H

N H2N OH

20.1 Suggested Reading 22.1 Suggested Reading Condé-Salazar L, Baz M, Guimaraens D et al Goh CL (1985) Occupational contact dermatitis (1995) Contact dermatitis in hairdressers: from soldering flux among workers in the elec- patch test results in 379 hairdressers tronics industry. Contact Dermatitis 13:85–90 (1980–1993). Am J Contact Dermat 6:19–23 Goh CL, Ng SK (1987) Airborne contact derma- titis to colophony in soldering flux. Contact Dermatitis 17:89–91 21 p-Aminodiphenylamine (Hydrochloride) 23 o-Aminophenol 4-Aminodiphenylamine (HCl), CI 76086 (CI 75085) 2-Aminophenol, CI 76520 CAS Registry Number [101-54-2] (CAS Reg- CAS Registry Number [95-55-6] istry Number [2198-59-6]) It is contained in hair dyes and can cause con- This substance was formerly used as a hair dye. tact dermatitis in hairdressers and consumers. Sensitization, when detected by patch testing, is relatively low in hairdressers. OH

NH2 NH2

N (.HCI) H 23.1 Suggested Reading

21.1 Suggested Reading Matsunaga K, Hosokawa K, Suzuki M et al (1988) Occupational allergic contact dermatitis Frosch PJ, Burrows D, Camarasa JG et al (1993) in beauticians. Contact Dermatitis 18:94–96 Allergic reactions to a hairdresser’s series: results from 9 European centers. Contact Der- matitis 28:180–183 24 p-Aminophenol

4-Aminophenol, Amino-4 Hydroxybenzene, 22 Aminoethylethanolamine Hydroxy-4 Aniline, CI 76550 CAS Registry Number [123-30-8] N-(2-Hydroxyethyl)ethylenediamine This hair dye is frequently implicated in con- CAS Registry Number [111-41-1] tact dermatitis in hairdressers, customers, or peo- Aminoethylethanolamine is a component of ple sensitized to para-phenylenediamine, by the colophony in soldering flux, which may cause way of “black henna” temporary tattoos. 38 J.-P. Lepoittevin and C. J. Le Coz

OH 25.1 Suggested Reading

Corazza M, Mantovani L, Trimurti L et al (1994) Occupational contact sensitization to ethylenediamine in a nurse. Contact Dermatitis 31:328–329

NH2 Dias M, Fernandes C, Pereira F et al (1995) Occu- pational dermatitis from ethylenediamine. Contact Dermatitis 33:129–130 24.1 Suggested Reading

Le Coz CJ, Lefebvre C, Keller F, Grosshans E 26 N,N-bis-(3-Aminopropyl) (2000) Allergic contact dermatitis caused by Dodecylamine skin painting (pseudotattooing) with black henna, a mixture of henna and p- N-(3-Aminopropyl)-N-dodecyl-1,3- phenylenediamine and its derivatives. Arch propanediamine Dermatol 136:1515–1517 CAS Registry Number [2372-82-9] Walker SL, Ead RD, Shackelton DB et al (2005) This alkylamine is contained in detergent- Two cases of occupational allergic contact der- disinfectants solutions for medical instruments. matitis to p-aminophenol in pharmaceutical It is also contained in association with 3- workers manufacturing paracetamol. Contact aminopropyl dodecylamine in liquid laundry dis- ® Dermatitis 52:290–291 infectants such as Aset aqua (Johnson Wax SpA, Rydelle).

25 Aminophylline N NH2

Theophylline Ethylenediamine

CAS Registry Number [317-34-0] NH2 This drug is a 2:1 mixture of the alkaloid the- ophylline and ethylenediamine (see below). It caused contact dermatitis in industrial plants, 26.1 Suggested Reading pharmacists, and nurses. Ethylenediamine is the sensitizer, and patch testing is generally positive Dibo M, Brasch J (2001) Occupational allergic to both ethylenediamine and aminophylline and contact dermatitis from N,N-bis negative to theophylline. (3-aminopropyl)dodecylamine and dimethyldidecylammonium chloride in two hospital staff. Contact Dermatitis 45:40 O H

N NH2 N 27 Ammonium Persulfate

N O N H2N Ammonium Peroxydisulfate CAS Registry Number [7727-54-0] 2 Persulfates are strong oxidizing agents widely used in the production of metals, textiles, photo- graphs, cellophane, rubber, adhesive papers, foods, soaps, detergents, and hair bleaches. Ammonium persulfate is used as a hair bleaching Dictionary of Contact Allergens: Chemical Structures, Sources, and References 39 agent. It may induce irritant dermatitis, (mainly) Gruppo Italiano Ricerca Dermatiti da Contatto e nonimmunologic contact urticaria, and allergic Ambientali. Contact Dermatitis 26:101–107 contact dermatitis and represents a major allergen in hairdressers. People reacting to ammonium persulfate also react to other persulfates such as 29 Amoxicillin potassium persulfate. CAS Registry Number [26787-78-0] OO Amoxicillin Trihydrate: CAS Registry Num- O O S NH SOO 4 ber [61336-70-7] 2 OO Amoxicillin Sodium Salt: CAS Registry Num- ber [34642-77-8] Amoxicillin is both a topical and a systemic 27.1 Suggested Reading sensitizer. Topical sensitization occurs in health- care workers. Systemic drug reactions are fre- Frosch PJ, Burrows D, Camarasa JG et al (1993) quent, such as urticaria, maculopapular rashes, Allergic reactions to a hairdresser’s series: baboon syndrome, acute generalized exanthema- results from 9 European centers. Contact Der- tous pustulosis, or even toxic epidermal necrosis. matitis 28:180–183 Cross-reactivity is common with ampicillin and Le Coz CJ, Bezard M (1999) Allergic contact can occur with other penicillins. cheilitis due to effervescent dental cleanser: combined responsibilities of the allergen HO persulfate and prosthesis porosity. Contact O Dermatitis 41:268–271 Van Joost T, Roesyanto ID (1991) Sensitization to N S persulphates in occupational and non- NH H occupational hand dermatitis. Contact Derma- 2 N titis 24:376–377 O

CO2H

28 Ammonium Thioglycolate 29.1 Suggested Reading Ammonium Mercaptoacetate CAS Registry Number [5421-46-5] Gamboa P, Jauregui I, Urrutia I (1995) Occupa- This substance is contained in “basic” perma- tional sensitization to aminopenicillins with nent waves solutions and causes contact dermati- oral tolerance to penicillin V. Contact Derma- tis in hairdressers. titis 32:48–49 Rudzki E, Rebandel P (1991) Hypersensitivity to semisynthetic penicillins but not to natural HS CO2 NH4 penicillin. Contact Dermatitis 25:192

28.1 Suggested Reading 30 Ampicillin

Frosch PJ, Burrows D, Camarasa JG et al (1993) CAS Registry Number [69-53-4] Allergic reactions to a hairdresser’s series: Ampicillin Trihydrate: CAS Registry Number results from 9 European centers. Contact Der- [7177-48-2] matitis 28:180–183 Ampicillin Sodium Salt: CAS Registry Num- Guerra L, Tosti A, Bardazzi F et al (1992) Contact ber [69-52-3] dermatitis in hairdressers: the Italian experience. 40 J.-P. Lepoittevin and C. J. Le Coz

Ampicillin caused contact dermatitis in a nurse 32 Amyl Cinnamyl Alcohol also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin) and in a pharma- 2-Pentyl-3-phenylprop-2-en-1-ol, Pentyl- ceutical factory worker. Systemic drug reactions cinnamic alcohol, α-Amyl-cinnamic alcohol, are common. Cross-reactivity is regular with Buxinol ampicillin and can occur with other penicillins. CAS Registry number [101-85-9] This scented molecule is very close to α-amyl- cinnamic aldehyde. Its presence is indicated by O name in cosmetics within the EU.

N S OH NH H 2 N O

CO2H

30.1 Suggested Reading 32.1 Suggested Reading

Gamboa P, Jauregui I, Urrutia I (1995) Occupa- Rastogi SC, Johansen JD, Menné T (1996) Natu- tional sensitization to aminopenicillins with ral ingredients based cosmetics. Content of oral tolerance to penicillin V. Contact Derma- selected fragrance sensitizers. Contact Derma- – titis 32:48–49 titis 34:423 426 Rudzki E, Rebandel P (1991) Hypersensitivity to semisynthetic penicillins but not to natural penicillin. Contact Dermatitis 25:192 33 Amylcinnamaldehyde

α-Amyl-cinnamic aldehyde, Ammylcinnamal, 31 Amprolium (Hydrochloride) 2-Benzylideneheptanal, 2-Pentylcinna- maldehyde, Jasminal CAS Registry Number [121-25-5] (CAS Registry CAS Registry Number [122-40-7] α Number [137-88-2]) -Amyl-cinnamic aldehyde is an oxidation Amprolium is an antiprotozoal agent used for product of amylcinnamic alcohol, a sensitizing “ the prevention of coccidiosis in poultry. fragrance, and one component of the fragrance mix.” It can also be a sensitizer in bakers. It has to N be mentioned by name in cosmetics within the EU.

N H

N O CI

31.1 Suggested Reading 33.1 Suggested Reading Nethercott JR, Holness DL (1989) Occupational Mancuso G, Staffa M, Errani A et al (1990) Occu- dermatitis in food handlers and bakers. J Am pational dermatitis in animal feed mill workers. Acad Dermatol 21:485–490 Contact Dermatitis 22:37–41 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 41

34 Anacardic Acids 35.1 Suggested Reading

Anacardic acids are mixtures of several analog Garcia-Bravo B, Pérez Bernal A, Garcia- molecules with alkyl chain (-R) of 13, 15, 17, or Hernandez MJ et al (1997) Occupational con- 19 carbons and 0–3 unsaturations. They are the tact dermatitis from anethole in food handlers. main cashew nut shell liquid component with Contact Dermatitis 37:38 cardol and can cause contact dermatitis in cashew nut workers. 36 Anisyl Alcohol OH O 4-Methoxybenzyl Alcohol, Methoxybenzene- OH , Anise Alcohol CAS Registry Number [105-13-5] Blend of o-, m-, and p-Methoxybenzyl Alco- R hol: CAS Registry number [1331-81-3] As a fragrance allergen, anisyl alcohol has to be mentioned by name in cosmetics within the EU. 34.1 Suggested Reading

Diogenes MJN, de Morais SM, Carvalho FF O (1996) Contact dermatitis among cashew nut workers. Contact Dermatitis 35:114–115 Hirao A, Oiso N, Matsuda H et al (2008) Occu- pational allergic contact dermatitis due to cashew nut oil. Contact Dermatitis 59:131–132

OH 35 Anethole

1-Methoxy-4-(1-propenyl)-benzene 36.1 Suggested Reading CAS Registry Number [104-46-1] Anethole is the main component of anise, star Schnuch A, Uter W, Geier J et al (2007) Sensiti- anise, and fennel oils. It is used in perfumes, food zation to 26 fragrances to be labeled according and cosmetic industries (toothpastes), bleaching to current European regulation. Contact Der- colors, and photography, and as an embedding matitis 57:1–10 material.

O 37 Antimony Trioxide

CAS Registry Number [1309-64-4] This hard shiny metal is often alloyed to other elements. It is used in various industrial fields such as batteries, printing machines, bearing, tex- tile, and ceramics. It caused positive patch test reactions in two workers in the ceramics industry.

Sb2O3 42 J.-P. Lepoittevin and C. J. Le Coz

37.1 Suggested Reading 39.1 Suggested Reading

Motolese A, Truzzi M, Giannini A et al (1995) Bircher AJ, Langauer Messmer S, Surber C et al Contact dermatitis and contact sensitization (1996) Delayed-type hypersensitivity to sub- among enamellers and decorators in the cutaneous lidocaine with tolerance to articaine: ceramics industry. Contact Dermatitis 28:59–62 confirmation by in vivo and in vitro tests. Con- tact Dermatitis 34:387–389 Duque S, Fernandez L (2004) Delayed-type 38 Arsenic and Arsenic Salts hypersensitivity to amide local anesthetics. (Sodium Arsenate) Allergol Immunopathol (Madr) 32:233–234

CAS Registry Number [7440-38-2] and CAS Registry Number [7778-43-0] 40 Atranol Arsenic salts are sensitizers but most often irritants. They are used in copper or gold extrac- 2,6-Dihydroxy-4-methyl-benzaldehyde tion, glass, feeds, weedkillers, insecticides, and CAS Registry number [526-37-4] ceramics. A recent case was reported in a crystal Atranol has been identified as a potent and factory worker with positive patch tests to sodium frequent allergen, occurring from the fragrance arsenate. material oak-moss absolute, which is of botanical

As AsO4H2Na origin.

38.1 Suggested Reading

Barbaud A, Mougeolle JM, Schmutz JL (1995) Contact hypersensitivity to arsenic in a crystal HO OH factory worker. Contact Dermatitis 33:272–273

O 39 Articaine (Hydrochloride) 40.1 Suggested Reading Carticaine (Hydrochloride) CAS Registry Number [23964-58-1] (CAS Andersen F, Andersen KH, Bernois A et al (2015) Registry Number [23964-57-0]) Reduced content of chloroatranol and atranol This local amide-type anesthetic is seldom in oak moss absolute significantly reduces the reported as allergenic even in patients sensitized elicitation potential of this fragrance material. to other amide-type molecules like lidocaine, Contact Dermatitis 72:75–83 prilocaine, mepivacaine, or bupivacaine. Johansen JD, Andersen KE, Svedman C et al (2003) Chloroatranol, an extremely potent O allergen hidden in perfumes: a dose response S elicitation study. Contact Dermatitis 49:180–184 O O Rastogi SC, Bossi R, Johansen JD, et al (2004) H N Content of oak moss allergens atranol and N chloroatranol in perfumes and similar prod- H ucts. Contact Dermatitis 50:367–370 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 43

41 Azaperone N

N S 4-Fluoro-4-[4-(2-pyridyl)-1-piperazininyl] H N butyrophenone N N CAS Registry Number [1649-18-9] N Azaperone is a sedative used in veterinary O2N medicine to avoid mortality of pigs during trans- portation. This alternative substance to chlor- promazine is a sensitizer and a photosensitizer. 42.1 Suggested Reading

Burden AD, Beck MH (1992) Contact hypersen- N sitivity to azathioprine. Contact Dermatitis 27:329–330 O N Lauerma A, Koivuluhta M, Alenius H (2001) N Recalcitrant allergic contact dermatitis from azathioprine tablets. Contact Dermatitis 44:129 F Soni BP, Sherertz EF (1996) Allergic contact der- matitis from azathioprine. Am J Contact Dermat 7:116–117 41.1 Suggested Reading

Brasch J, Hessler HJ, Christophers E (1991) 43 Basic Red 22 Occupational (photo)allergic contact dermati- tis from azaperone in a piglet dealer. Contact Synacril Red 3B – Dermatitis 25:258 259 CAS Registry Number [12221-52-2] This monoazoic dye was reported as allergenic in a PPD-free hair coloring mousse. 42 Azathioprine

6-(1-Methyl-4-nitroimidazol-5-ylthio)purine N N N CAS Registry Number [446-86-6] N This immunosuppressive and antineoplastic N drug is derived from 6-mercaptopurine. It caused N allergic contact dermatitis in a mother crushing tablets for her leukemic son, and occupational dermatitis in a pharmaceutical reconditioner of old tablet packaging machines, and in a produc- 43.1 Suggested Reading tion mechanic working in packaging for a phar- maceutical company. Salim A, Orton D, Shaw S (2001) Allergic contact dermatitis from Basic Red 22 in a hair-coloring mousse. Contact Dermatitis 45:123 44 J.-P. Lepoittevin and C. J. Le Coz

44 Basic Red 46 Nino M, Balato A, Ayala F, Balato N (2007) Allergic contact dermatitis due to levobunolol CAS Registry Number [12221-69-1] with cross-sensitivity to befunolol. Contact This monoazoic textile dye seems to be an Dermatitis 56:53–54 important cause of foot dermatitis, being a fre- quent allergen in acrylic socks. It caused contact dermatitis in two workers in the textile industry. 46 Benomyl

CAS Registry Number [17804-35-2] N N N Benomyl is a fungicide, derived from benz- N imidazole. Cases of sensitization were reported N in horticulturists and florists. It is however, at N most, a weak sensitizer, with possible false- positive patch reactions or with cross-reactions after previous exposure to other fungicides. 44.1 Suggested Reading H O Opie J, Lee A, Frowen K, Fewings J et al (2003) N Foot dermatitis caused by the textile dye Basic Red 46 in acrylic blend socks. Contact Derma- N H titis 49:297–303 N Soni BP, Sherertz EF (1996) Contact dermatitis in N O the textile industry: a review of 72 patients. Am J Contact Dermat 7:226–230 O

45 Befunolol 46.1 Suggested Reading

CAS Registry Number [39552-01-7] Jung HD, Honemann W, Kloth C et al (1989) Befunolol was implicated in allergic contact Kontaktekzem durch Pestizide in der dermatitis due to beta-blocker agents in eyedrops. Deutschen Demokratischen Republik. – Cross-sensitivity has been described with Dermatol Monats 175:203 214 levobunolol. Larsen AI, Larsen A, Jepsen JR et al (1990) Con- tact allergy to the fungicide benomyl? Contact Dermatitis 22:278–281 O OH H O’Malley M, Rodriguez P, Maibach HI (1995) Pes- N ticide patch testing: California nursery workers H N 2 and controls. Contact Dermatitis 32:61–62

HO 47 Benzalkonium Chloride 45.1 Suggested Reading CAS Registry Number [8001-54-5] Giordano-Labadie F, Lepoittevin JP, Calix I et al This quaternary ammonium cationic surfactant (1997) Allergie de contact aux β-bloqueurs des is a mixture of alkyl, dimethyl, and benzyl ammo- collyres: allergie croisée? Ann Dermatol nium chlorides (-R). It is an irritant rather than a Venereol 124:322–324 sensitizer but may cause allergic contact dermati- tis from creams, detergents/antiseptics, ophthal- mic preparations, and in nursing, veterinary, Dictionary of Contact Allergens: Chemical Structures, Sources, and References 45 dental, and medical personnel. Its presence was 48.1 Suggested Reading observed in plaster of Paris. Aalto-Korte K, Ackermann L, Henriks-Eckerman ML et al (2007) 1,2-benzisothiazolin-3-one in disposable polyvinyl chloride gloves for med- ical use. Contact Dermatitis 57:365–370 R Burden AD, O’Driscoll JB, Page FC et al (1994) CI N Contact hypersensitivity to a new iso- thiazolinone. Contact Dermatitis 30:179–180 Dias M, Lamarao P, Vale T (1992) Occupational contact allergy to 1,2-benzisothiazolin-3-one 47.1 Suggested Reading in the manufacture of air fresheners. Contact Dermatitis 27:205–206 Basketter DA, Marriott M, Gilmour NJ et al Meysman T, Goossens A (2017) Occupational (2004) Strong irritants masquerading as skin allergic contact dermatitis caused by allergens: the case of benzalkonium chloride. benzisothiazolinone in printing ink and soap. Contact Dermatitis 50:213–217 Contact Dermatitis 76:120–122 Corazza M, Virgili A (1993) Airborne allergic Sanz-Gallén P, Planas J, Martinez P et al (1992) contact dermatitis from benzalkonium chlo- Allergic contact dermatitis due to ride. Contact Dermatitis 28:195–196 1,2-benzisothiazolin-3-one in paint manufac- Klein GF, Sepp N, Fritsch P (1991) Allergic reac- ture. Contact Dermatitis 27:271–272 tions to benzalkonium chloride? Do the use test! Contact Dermatitis 25:269–270 Stanford D, Georgouras K (1996) Allergic contact 49 Benzophenones dermatitis from benzalkonium chloride in plas- ter of Paris. Contact Dermatitis 35:371–372 (BZP) and substituted BZP num- bered 1–12, trademark Uvinul®, are photo-screen agents widely used in and in cos- 48 Benzisothiazolinone (BIT) metics, such as “antiaging” creams and hair sprays and shampoos, paints, and plastics. The hypo- 1,2-Benzisothiazolin-3-one, Proxan, Proxel PL lipemiant drug fenofibrate is also a substituted CAS Registry Number [2634-33-5] benzophenone. BIT, both an irritant and a skin sensitizer, is Benzophenone, Unsubstituted widely used in industry as a preservative in water- CAS Registry Number [119-61-9] based solutions such as pastes, paints, and cutting Unsubstituted benzophenone is largely used in oils. Occupational dermatitis has been reported chemical applications. It acts as a marker for mainly due to cutting fluids and greases, in paint photoallergy to ketoprofen. manufacturers, pottery mold-makers, acrylic Benzophenone 1 emulsions manufacturers, plumber, printers and Benzoresorcinol, Uvinul 400 lithoprinters, paper makers, analytical laboratory, CAS Registry Number [131-56-6] rubber factory, and employees manufacturing air BZP-1 is used in paints, plastics, and nail var- fresheners. It is also a preservative in vinyl gloves. nishes, for example. Benzophenone-2 O 2,2,4,4-Tetrahydroxybenzophenone CAS Registry Number [131-55-5] N H BZP-2 is widely used in perfumes to prevent S their degradation due to light. It can cause allergic contact dermatitis. 46 J.-P. Lepoittevin and C. J. Le Coz

O OH O OH O OH

HO OH O BZP BZP-2 BZP-3 O OH O OH

O O BZP-10 BZP-4 SO3H O O

O O

CI Fenofibrate

Benzophenone-3 Guin JD (2000) Eyelid dermatitis from benzophe- none used in nail enhancement. Contact Der- CAS Registry Number [131-57-7] matitis 43:308–309 BZP-3isusedasadirectsunscreenagentandin Jacobs MC (1998) Contact allergy to antiaging creams. Allergic reactions have been benzophenone-2 in toilet water. Contact Der- reported. Cross-reactivity is expected in an average matitis 39:42 of one in four patients photoallergic to ketoprofen. Knobler E, Almeida L, Ruzkowski AM et al Benzophenone-4 (1989) Photoallergy to benzophenone. Arch Dermatol 125:801–804 CAS Registry Number [4065-45-6] Le Coz CJ, Bottlaender A, Scrivener JN et al BZP-4 is widely used in cosmetics, particularly (1998) Photocontact dermatitis from shampoos and hair products. Cross-reactivity is ketoprofen and tiaprofenic acid: cross- rarely expected in patients photoallergic to reactivity study in 12 consecutive patients. ketoprofen. Contact Dermatitis 38:245–252 Benzophenone-10 Matthieu L, Meuleman L, van Hecke E et al Mexenone (2004) Contact and photocontact allergy to CAS Registry Number [1641-17-4] ketoprofen. The Belgian experience. Contact BZP-10 is exceptionally positive in Dermatitis 50:238–241 ketoprofen-photosensitive patients.

50 Benzoyl Peroxide 49.1 Suggested Reading CAS Registry Number [94-36-0] Alanko K, Jolanki R, Estlander T et al (2001) Benzoyl peroxide is an oxidizing agent widely Occupational allergic contact dermatitis from employed in acne topical therapy. It is also used as benzophenone-4 in hair-care products. Contact a polymerization catalyst of dental or industrial Dermatitis 44:188 plastics and as a decolorizing agent of flours, oils, Collins P, Ferguson J (1994) Photoallergic contact fats, and waxes. Irritant or allergic dermatitis may dermatitis to oxybenzone. Br J Dermatol affect workers in the electronics and plastics 131:124–129 (epoxy resins and catalysts) industries, Dictionary of Contact Allergens: Chemical Structures, Sources, and References 47 electricians, ceramic workers, dentists and dental 51.1 Suggested Reading technicians, laboratory technicians, bakers, and acne patients. As it was contained in candles, it Foti C, Vena GA, Angelini G (1992) Occupational also induced contact dermatitis in a sacristan. contact allergy to benzydamine hydrochloride. Patch tests may be irritant. Contact Dermatitis 27:328–329 Lasa Elgezua O, Egino Gorrotxategi P, Gardeazabal García J et al (2004) Photoallergic O hand eczema due to benzydamine. Eur J O Dermatol 14:69–70 O

O 52 Benzyl Alcohol

CAS Registry Number [100-51-6] 50.1 Suggested Reading Benzyl alcohol is mainly a preservative, mostly used in topical antimycotic or corticoste- Quirce S, Olaguibel JM, Garcia B et al (1993) roid ointments. It is also a component catalyst for Occupational airborne contact dermatitis due epoxy resins and is contained in the color devel- to benzoyl peroxide. Contact Dermatitis oper C-22. As a fragrance allergen, it has to be – 29:165 166 mentioned by name in cosmetics within the EU. Rustemeyer T, Frosch PJ (1996) Occupational skin diseases in dental laboratory technicians. Clinical picture and causative factors. Contact OH Dermatitis 34:125–133 Tsovilis E, Crépy MN, Jonathan AM et al (2005) Occupational contact dermatitis due to a marbler’s exposure to benzoyl peroxide. Con- tact Dermatitis 52:117–118 52.1 Suggested Reading

Lodi A, Mancini LL, Pozzi M et al (1993) Occu- 51 Benzydamine Hydrochloride pational airborne allergic contact dermatitis in parquet layers. Contact Dermatitis 29:281–282 CAS Registry Number [132-69-4] Scheman AJ, Katta R (1997) Photographic aller- It is a anti-inflammatory drug gens: an update. Contact Dermatitis 37:130 used both topically and systemically. It has been Sestini S, Mori M, Francalanci S (2004) Allergic reported as a sensitizer and a photosensitizer. contact dermatitis from benzyl alcohol in mul- tiple medicaments. Contact Dermatitis 50:316–317

53 Benzyl Benzoate N HCI N Benzoic Acid Phenylmethyl Ester N CAS Registry Number [120-51-4] Benzyl benzoate is the ester of benzyl alcohol O and benzoic acid. It is contained in Myroxylon pereirae and Tolu balsam. It is used in acaricide preparations against Sarcoptes scabiei or as a 48 J.-P. Lepoittevin and C. J. Le Coz pediculicide. Direct contact may cause skin irrita- by benzyl salicylate in hair products. Contact tion but rarely allergic contact dermatitis. As a Dermatitis. https://doi.org/10.1111/cod.13038 fragrance allergen, benzyl benzoate has to be mentioned by name in EU cosmetics. 55 Benzylpenicillin O Penicillin G O CAS Registry Number [61-33-6] Benzylpenicillin is actually used only intrave- nously. It was formerly a frequent cause of contact allergy in health-care workers. Facial contact der- matitis was recently reported in a nurse. 53.1 Suggested Reading H Meneghini CL, Vena GA, Angelini G (1982) Con- N tact dermatitis to scabicides. Contact Dermati- S tis 8:285–286 O Schnuch A, Uter W, Geir J et al (2007) Sensitiza- N tion to 26 fragrances to be labbed according to O current European regulation. Contact Dermati- COOH tis 57:1–10

55.1 Suggested Reading 54 Benzyl Salicylate Pecegueiro M (1990) Occupational contact der- Benzyl-o-hydroxybenzoate, 2-Hydroxybenzoic matitis from penicillin. Contact Dermatitis Acid Phenylmethyl Ester 23:190–191 CAS Registry Number [118-58-1] Benzyl salicylate is used as fixer in perfumery and preparations. As a (weak) perfume 56 BHA sensitizer, it has to be listed by name in cosmetic preparations in the EU. Butylated Hydroxyanisole CAS Registry Number [25013-16-5] OH O BHA is an antioxidant widely used in cos- metics and food. Contained in pastry, it can induce sensitization in caterers. O

O

54.1 Suggested Reading

Larsen W, Nakayama H, Lindberg M et al (1996) Fragrance contact dermatitis: a worldwide multicenter investigation (Part I). Am J Con- OH tact Dermat 7:77–83 Tous-Romero F, Prieto-Barrios J, Andrés-Lencina et al (2018) Allergic contact dermatitis caused Dictionary of Contact Allergens: Chemical Structures, Sources, and References 49

56.1 Suggested Reading Bioban® CS-1135 can be a sensitizer per se, in patients without formaldehyde allergy. Acciai MC, Brusi C, Francalanci Giorgini S et al (1993) Allergic contact dermatitis in caterers. O O Contact Dermatitis 28:48

N N 57 BHT

Butylated Hydroxytoluene, 2,6-di-(tert-Butyl)-p- cresol 58.1 Suggested Reading CAS Registry Number [128-37-0] This antioxidant is contained in food, adhesive Brinkmeier T, Geier J, Lepoittevin JP et al (2002) glues, industrial oils, and greases, including cut- Patch test reactions to Biobans in metalworkers ting fluids. Sensitization seems very rare. are often weak and not reproducible. Contact Dermatitis 47:27–31 OH Kanerva L, Estlander T, Jolanki R (1994) Occu- pational allergic contact dermatitis caused by thiourea compounds. Contact Dermatitis 31:242–248

59 Bioban® CS-1246

Oxazolidine, 5-Ethyl-1-aza-3,7-dioxa-bicyclo- 57.1 Suggested Reading 3,3,0 Octane CAS Registry Number [7747-35-5], [504-76-7] Flyvholm MA, Menné T (1990) Sensitizing risk Bioban® CS-1246 is a relatively old formalde- of butylated hydroxytoluene based on expo- hyde releaser, used in cutting oils. Bioban® sure and effect data. Contact Dermatitis CS-1248 is a mixture of Bioban® CS-1246 and 23:341–345 Bioban® P-1487.

58 Bioban® CS-1135

3,4-Dimethyloxazolidine + 3,4,4-Trimethy- O loxazolidine O N CAS Registry Number [81099-36-7] (CAS Registry Number [51200-87-4] + CAS Registry Number [75673-43-7]) Bioban® CS-1135 is the trade name for the two 59.1 Suggested Reading compounds 3,4-dimethyloxazolidine (74.8%) and 3,4,4-trimethyloxazolidine (2.5%). It is a formal- Brinkmeier T, Geier J, Lepoittevin JP et al (2002) dehyde releaser used as a preservative in latex Patch test reactions to Biobans in metalworkers paints and emulsions and in cooling fluids. are often weak and not reproducible. Contact – Dimethyl oxazolidine is found in some cosmetics. Dermatitis 47:27 31 50 J.-P. Lepoittevin and C. J. Le Coz

® 60 Bioban P-1487 footwear, and dental materials. It is also a possible sensitizer in vinyl gloves. 4-(2-Nitrobutyl)morpholine + 4,4-(2-Ethyl-2- nitrodimethylene)dimorpholine CAS Registry Number [37304-88-4] (CAS Registry Number [2224-44-4] + CAS Registry Number [1854-23-5]) ® Bioban P-1487 is a mixture of HO OH 4-(2-nitrobutyl)morpholine CAS Registry Num- ber [2224-44-4] 70% and 4,4-(2-ethyl-2- 61.1 Suggested Reading nitrodimethylene)dimorpholine or 4,4-(2-ethyl- 2-nitro-1,3-propanediyl)-bis-morpholine CAS Aalto-Korte K, Pesonen M, Suuronen K (2015) Registry Number [1854-23-5] 20%. Both ingredi- Occupational allergic contact dermatitis ents can be the sensitizers. It is used as a preser- caused by epoxy chemicals: occupations, sen- vative in metalworking cutting fluids. Bioban® sitizing products and diagnosis. Contact Der- CS-1248 is a mixture of Bioban® CS-1246 and matitis 73:336–342 Bioban® P-1487. Jolanki R, Kanerva L, Estlander T (1995) Occu- pational allergic contact dermatitis caused by epoxy diacrylate in ultraviolet-light-cured paint, and bisphenol A in dental composite N NN resin. Contact Dermatitis 33:94–99 O NO O NO2 O 2 Matthieu L, Godoi AFL, Lambert J et al (2004) Occupational allergic contact dermatitis from bisphenol A in vinyl gloves. Contact Dermati- 60.1 Suggested Reading tis 49:281–283

Brinkmeier T, Geier J, Lepoittevin JP et al (2002) Patch test reactions to Biobans in metalworkers 62 Bisphenol A Diglycidyl Ether are often weak and not reproducible. Contact (DGEBA) Dermatitis 47:27–31 Gruvberger B, Bruze M, Zimerson E (1996) Con- BADGE tact allergy to the active ingredients of Bioban CAS Registry Number [1675-54-3] P 1487. Contact Dermatitis 35:141–145 Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular- 61 Bisphenol A weight monomer BADGE (molecular weight 340 g/mol), the dimer having much a lower sensi- Diphenylolpropane, Isopropylidene Diphenol tization power. This allergen caused contact der- CAS Registry Number [80-05-7] matitis in six workers in a plant producing printed Bisphenol A is used with epichlorhydrin for circuits boards made of copper sheets and fiber the synthesis of epoxy resins bisphenol A type, for glass fabric impregnated with a brominated epoxy unsaturated polyester and polycarbonate resins, resin. It can be contained in adhesives. and for epoxy di(meth)acrylates. In epoxy resins, it leads to bisphenol A diglycidyl ether, which is the monomer of bisphenol A-based epoxy resins. Reports of bisphenol A sensitization are rare and concern workers at epoxy resin plants, after con- O O tact with fiber glass, semisynthetic waxes, O O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 51

62.1 Suggested Reading OH OH

Aalto-Korte K, Pesonen M, Suuronen K (2015) Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sen- sitizing products and diagnosis. Contact Der- HO OH matitis 73:336–342 Bruze M, Edenholm M, Engenström K et al (1996) Occupational dermatoses in a Swedish aircraft plant. Contact Dermatitis 34:336–340 Hansson C (1994) Determination of monomers in 63.1 Suggested Reading epoxy resin hardened at elevated temperatures. – Contact Dermatitis 31:333 334 Aalto-Korte K, Pesonen M, Suuronen K (2015) Occupational allergic contact dermatitis o,p p,p caused by epoxy chemicals: occupations, sen- 63 -Bisphenol F and - sitizing products and diagnosis. Contact Der- Bisphenol F matitis 73:336–342 Bruze M, Fregert S, Zimerson E (1985) Contact 2,4-Dihydroxy-diphenylmethane and allergy to phenol-formaldehyde resins. Contact 4,4-Dihydroxy-diphenylmethane Dermatitis 12:81–86 CAS Registry Number [2467-03-0] and CAS Registry Number [620-92-8] o,p-Bisphenol F and p,p-bisphenol F are aller- 64 Bisphenol F Diglycidyl Ether genic components of phenol-formaldehyde resins (DGEBF) resol-type. (a) p,p-Diglycidyl Ether of Bisphenol F: CAS Registry Number [2095-03-6]

O O O 1. O

O O O O O O 2.

3.

O 52 J.-P. Lepoittevin and C. J. Le Coz

(b) o,p-Diglycidyl Ether of Bisphenol F: CAS Pontén A, Zimerson E, Bruze M (2004) Contact Registry Number [57469-08-5] allergy to the isomers of diglycidyl ether of (c) o,o-Diglycidyl Ether of Bisphenol F: CAS bisphenol F. Acta Derm Venereol (Stockh) Registry Numbers [39817-09-9] and [54208- 84:12–17 63-8]

Epoxy resins based on Bisphenol F, also called 65 Brominated Epoxy Resin phenolic Novolac, contain bisphenol F diglycidyl ether, which has three sensitizing isomers. As a component of nondiglycidyl ether of DGEBF has a greater resistance than DGEBA. bisphenol A epoxy resins, brominated epoxy Contact allergy to bisphenol-F-based epoxy resins resin caused contact dermatitis in a cleaner of is rarer than that due to bisphenol A-based resins worksites in a condenser factory, where con- and is frequently acquired with flooring materials densers were filled with a mixture made of an and putty. epoxy resin.

Br Br

R R O O O O

OH Br Br OH

R = O O

64.1 Suggested Reading 65.1 Suggested Reading

Aalto-Korte K, Pesonen M, Suuronen K (2015) Kanerva L, Jolanki R, Estlander T (1991) Allergic Occupational allergic contact dermatitis contact dermatitis from nondiglycidyl-ether-of- caused by epoxy chemicals: occupations, sen- bisphenol-A epoxy resins. Contact Dermatitis sitizing products and diagnosis. Contact Der- 24:293–300 matitis 73:336–342 Bruze M, Edenholm M, Engenström K et al (1996) Occupational dermatoses in a Swedish 66 1-Bromo-3-Chloro-5,5- aircraft plant. Contact Dermatitis 34:336–340 Dimethylhydantoin Pontén A, Bruze M (2001) Contact allergy to epoxy resin based on diglycidyl ether of Di-Halo, 1-Bromo-3-chloro-5,5-dimethyl-2,4- Bisphenol F. Contact Dermatitis 44:98–99 imidazolidinedione, Agribrom, Slimicide C 77P Dictionary of Contact Allergens: Chemical Structures, Sources, and References 53

CAS Registry Number [16079-88-2] Br This chlorinated and brominated product is HO employed in agriculture as a fungicide, for wood preservation. When used to sanitize pools and Br Br spas, releasing both chlorine and bromine deriva- O OH O OH O tives, it can induce irritant or allergic contact 1. 2. 3. dermatitis.

O 67.1 Suggested Reading CI N Jensen CD, Andersen KE (2003) Allergic contact dermatitis from a paper mill slimicide N O containing 2-bromo-4-hydroxyacetophenone. Br Am J Contact Dermat 14:41–43

66.1 Suggested Reading 68 Bronopol

Dalmau G, Martinez-Escala ME, Gazquez V et al 2-Bromo-2-nitro-1,3-propanediol (2012) Swimming pool contact dermatitis CAS Registry Number [52-51-7] caused by 1-bromo-3-chloro-5,5-dimethyl Bronopol is a preservative sometimes consid- hydantoin. Contact Dermatitis 66:335–339 ered as a formaldehyde releaser. It was reported to Rycroft RJG, Penny PT (1983) Dermatoses asso- be an allergen in cosmetics, cleaning agents, dairy ciated with brominated swimming pools. Br workers, and a lubricant jelly used for ultrasound Med J (Clin Res Ed) 287:462 examination. Sasseville D, Moreau L (2004) Contact allergy to

1-bromo-3chloro-5, 5-dimethylhydantoin in Br NO2 – spa water. Contact Dermatitis 50:323 324 HO OH

67 Bromohydroxyacetophenone 68.1 Suggested Reading (a) 2-Bromo-4-hydroxyacetophenone, 1-(4-Hydro- Grattan CEH, Harman RRM, Tan RSH (1986) xyphenyl)-2-bromoethanone: CAS Registry Num- Milk recorder dermatitis. Contact Dermatitis ber [2491-38-5] 14:217–220 (b) 2-Bromo-2-hydroxyacetophenone (6CI, Wilson CL, Powell SM (1990) An unusual cause 7CI, 8CI): CAS Registry Number [2491-36-3] of allergic contact dermatitis in a veterinary (c) 5-Bromo-2-hydroxyacetophenone (6CI, surgeon. Contact Dermatitis 23:42–43 7CI, 8CI), 1-(5-Bromo-2-hydroxyphenyl) ethanone: CAS Registry Number [1450-75-5] Those substances are biocides used in emul- 69 Budesonide sions, paints, adhesives, waxes, and polishes. They are both irritants and sensitizers. 2-Bromo- Budesonide 4-hydroxyacetophenone used as a slimicide pro- CAS Registry number [51333-22-3] voked sensitization after an accidental spillage R-Budesonide and recurrent allergic contact dermatitis at a CAS Registry Number [51372-29-3] workplace. S-Budesonide 54 J.-P. Lepoittevin and C. J. Le Coz

HO O HO O H O O HO HO O O

H H O O R -Budesonide HO O O HO H O

H

O S -Budesonide

CAS Registry Number [51372-28-2] Ponten A (2006) Airborne occupational contact Budesonide is a , a blend of two dermatitis caused by extremely low concentra- diastereosiomers. tions of budesonide. Contact Dermatitis R-Budesonide is a marker of the B group of 55:121–124 . Such molecules have a cis-diol moiety or an acetal moiety on the C16 and C17 of the D cycle. One side chain is possible on C21. The 70 Bufexamac B group comprises , budesonide, or prednacinolone, flunisolide, CAS Registry Number [2438-72-4] fluocinolone and its acetonide, fluocinonide, Bufexamac is an arylacetic nonsteroidal anti- fluclorolone and its acetonide, , and inflammatory drug. It induces allergic contact der- acetonide, benetonide, diacetate, and hexa- matitis, eczematous or erythema multiforme-like cetonide of . type, and even generalized eruptions like acute S-Budesonide is a marker of the D2 group of generalized exanthematous pustulosis. corticosteroids. Such molecules are non- methylated in C16 and have an ester function in H C17. They comprise hydrocortisone 17-butyrate, N hydrocortisone-17-valerate, hydrocortisone OH aceponate, aceponate, and O . O

69.1 Suggested Reading 70.1 Suggested Reading

Lepoittevin JP, Drieghe J, Dooms-Goossens A Belhadjali H, Ghannouchi N, Njim L et al (2008) (1995) Studies in patients with corticosteroid Acute generalized exanthematous pustulosis contact allergy. Understanding cross-reactivity induced by bufexamac in an atopic girl. Con- among different . Arch Dermatol tact Dermatitis 58:247–248 131:31–37 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 55

Kurumaji Y (1998) Photo Koebner phenomenon 72 1,4-Butanediol Diglycidyl Ether in erythema-multiforme-like eruption induced by contact dermatitis due to bufexamac. Der- 5CAS Registry Number [2425-79-8] matology 197:183–186 This substance is a reactive diluent in epoxy resins.

71 Buprenorphine O O O CAS registry Number [52485-79-7] O This semisynthetic opioid analgesic drug is derived from thebaine. It can be used parenterally, orally, and topically with transdermal systems 72.1 Suggested Reading (TDS). In case of localized or generalized allergic contact dermatitis due to buprenorphine in TDS, Jolanki R, Estlander T, Kanerva L (1987) Contact TDS containing fentanyl can be safely used. allergy to an epoxy reactive diluent: 1,4-butanediol diglycidyl ether. Contact Der- HO matitis 16:87–92 Jolanki R, Kanerva L, Estlander T et al (1990) Occupational dermatoses from epoxy resin compounds. Contact Dermatitis 23:172–183 O N 73 N-Butyl-1,2-Benzisothiazolin-3- one (BBIT) H3CO H HO 1,2-Benzisothiazol-3(2H)-one (H3C)3C CH3 CAS Registry Number [4299-07-4] This isothiazolinone derivative is used as pre- servative in water-based products such as wallpa- 71.1 Suggested Reading per adhesive, epoxy resins, silicone sealants, or metalworking fluids. A case of occupational con- Kaae J, Menné T, Thyssen JP (2012) Systemic tact dermatitis to N-butyl-1,2-benzisothiazolin-3- contact dermatitis following oral exposure to one present as preservative in a cutting fluid was tramadol in a patient with allergic contact der- reported in a metal worker. matitis caused by buprenorphine. Contact Der- matitis 66:106–107 Pérez-Pérez L, Cabanillas M, Loureiro M et al (2008) Allergic contact dermatitis due to trans- dermal buprenorphine. Contact Dermatitis 58:310–312 Van der Hulst K, Parera Amer E, Jacobs C et al (2008) Allergic contact dermatitis from trans- 73.1 Suggested Reading dermal buprenorphine. Contact Dermatitis 59:366–369 Dahlin J, Isaksson M (2015) Occupational contact dermatitis caused by N-butyl-1,2- benzisothiazolin-3-one in a cutting fluid. Con- tact Dermatitis 73:60–62 56 J.-P. Lepoittevin and C. J. Le Coz

74 N-tert-Butyl-bis- Schliemann-Willers S, Bauer A, Elsner P (2000) (2-Benzothiazole) Sulfenamide Occupational contact dermatitis from diethylene glycol monobutyl ether in a podia- CAS Registry Number [3741-80-8] trist. Contact Dermatitis 43:225 This mercaptobenzothiazole-sulfenamide chemical is used as an accelerator in rubber vulcanization. 76 p-tert-Butylcatechol

N CAS Registry Number [98-29-3] S p-tert-Butylcatechol is specially prepared by reacting the impure catechol fraction with tertiary S N butyl alcohol. It is used for its various properties S (inhibitor of polymerization and antioxidizing agent) in the manufacture of rubber, plastics, and N paints, in the preparation of petrolatum products, S and as an antioxidant in oils. It may induce vitiligo.

OH

OH 74.1 Suggested Reading

Le Coz CJ (2004) Fiche d’éviction en cas d’hypersensibilité au mercaptobenzothiazole et au mercapto mix. Ann Dermatol Venereol 131:846–848

75 Butyl Carbitol 76.1 Suggested Reading

Diethylene Glycol Monobutyl Ether Gawkrodger DJ, Cork MJ, Bleehen SS (1991) CAS Registry Number [112-34-5] Occupational vitiligo and contact sensitivity This organic solvent belongs to the carbitols to para-tertiary butyl catechol. Contact Derma- group and is included in water-based liquids such titis 25:200–201 as paints, surface cleaners, polishes, and disinfec- tants. It is considered to be an exceptional allergen. 77 n-Butyl Glycidyl Ether

H O CAS Registry Number [2426-08-6] O O A reactive diluent used to reduce viscosity of epoxy resins bisphenol A type.

75.1 Suggested Reading O O Berlin K, Johanson G, Lindberg M (1995) Hyper- sensitivity to 2-(2-butoxyethoxy)ethanol. Con- tact Dermatitis 32:54 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 57

77.1 Suggested Reading 79 p-tert-Butyl-alpha- methylhydrocinnamic Holness DL, Nethercott JR (1993) The perfor- Aldehyde mance of specialized collections of bisphenol A epoxy resin system components in the eval- Lilial®, 2-(4-tert-butylbenzyl)propionaldehyde, uation of workers in an occupational health 4-(1,1-Dimethylethyl)-α-methyl-benzenepropanal, clinic population. Contact Dermatitis p-tert-butyl-α-methylhydrocinnamaldehyde, 28:216–219 Lilestral Jolanki R, Kanerva L, Estlander T et al (1990) CAS Registry Number [80-54-6] Occupational dermatoses from epoxy resin Lilial® is a synthetic compound listed as a compounds. Contact Dermatitis 23:172–183 fragrance allergen. Its presence is indicated on cosmetics within the EU.

78 tert-Butylhydroquinone O 2-tert-Butylhydroquinone, TBHQ CAS Registry Number [1948-33-0] This antioxidant has seldom been reported as a sensitizer, mainly in cosmetics (lipsticks, lip gloss, hair dyes) or in cutting oils. Simultaneous reactions/cross-reactions have been described to 79.1 Suggested Reading butylhydroxyanisole (BHA) and less frequently to butylhydroxytoluene (BHT), but not to Bennike NH, Zachariae C, Johansen JD (2017) hydroquinone. Non-mix fragrances are top sensitizers in con- secutive dermatitis patients – a cross-sectional OH study of the 26 EU-labelled fragrance aller- gens. Contact Dermatitis 77:270–279 Giménez-Arnau E, Andersen KE, Bruze M et al (2001) Identification of Lilial as a fragrance sensitizer in a perfume by bioassay-guided chemical fractionation and structure-activity OH relationships. Contact Dermatitis 43:351–358

78.1 Suggested Reading 80 Butylene Glycol

Aalto-Korte K (2008) Allergic contact dermatitis 1,3-Butylene Glycol, 1,3-Butanediol from tertiary-butylhydroquinone (TBHQ) in a CAS Registry Number [107-88-0] vegetable hydraulic oil. Contact Dermatitis This dihydric alcohol is used for its humectant 43:303 and preservative potentiator properties in cos- Le Coz CJ, Schneider GA (1998) Contact derma- metics, topical medicaments and polyurethane, titis from tertiary-butylhydroquinone in a hair polyester, cellophane, and cigarettes. It has similar dye, with cross-sensitivity to BHA and BHT. properties but is less irritant than propylene gly- Contact Dermatitis 39:39–40 col. Contact allergies seem to be rare.

OH

OH 58 J.-P. Lepoittevin and C. J. Le Coz

80.1 Suggested Reading butylphenol-formaldehyde resin (PTBP-F-R) in Northern Ireland. Contact Dermatitis Diegenant C, Constandt L, Goossens A (2000) 29:144–146 Allergic contact dermatitis due to Mancuso G, Reggiani M, Berdondini RM (1996) 1,3-butylene glycol. Contact Dermatitis Occupational dermatitis in shoemakers. Con- 43:324–235 tact Dermatitis 34:17–22 Matsunaga K, Sugai T, Katoh J et al (1997) Group Shono M, Ezoe K, Kaniwa MA et al (1991) Aller- study on contact sensitivity of 1,3-butylene gic contact dermatitis from para-tertiary- glycol. Environ Dermatol 4:195–205 butylphenol-formaldehyde resin (PTBP-FR) Tamagawa-Mineoka, Katoh N, Kishimoto S in athletic tape and leather adhesive. Contact (2007) Allergic contact dermatitis due to Dermatitis 24:281–288 1,3-butylene glycol and . Contact Der- Tarvainen K (1995) Analysis of patients with matitis 56:297–298 allergic patch test reactions to a plastics and glue series. Contact Dermatitis 32:346–351

81 Para-tert-Butylphenol 82 Caffeic Acid Dimethyl Allylic CAS Registry Number [98-54-4] Ester Para-tert-butylphenol is used with formalde- hyde to produce the polycondensate p-tert- 3-Methyl-2-butenyl-caffeate butylphenol-formaldehyde resins (PTBPFR). CAS Registry Number [108084-13-7] Major occupational sources are neoprene glues This is the major allergen of poplar bud resins and adhesives in industry, in the shoemaking and and of propolis, the bee glue derived almost exclu- leather industries, or in car production. It is also sively from poplar buds. used as a box preservative in box and furniture manufacture and in the production of casting HO molds, car brake linings, insulated electrical cables, adhesives, printing inks, and paper lami- O nates. Para-tert-butylphenol seems to be the HO sensitizer. O

OH 82.1 Suggested Reading

Lamminpää A, Estlander T, Jolanki R et al (1996) Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- tis 34:330–335 Oliwiecki S, Beck MH, Hausen BM (1992) Occu- pational contact dermatitis from caffeates in poplar bud resin in a tree surgeon. Contact 81.1 Suggested Reading Dermatitis 27:127–128

Handley J, Todd D, Bingham A et al (1993) Aller- gic contact dermatitis from para-tertiary- Dictionary of Contact Allergens: Chemical Structures, Sources, and References 59

83 Caprylhydroxamic Acid 84.1 Suggested Reading

N-Hydroxy-caprylohydroxamic acid, N-Hydroxy- Peluso AM, Tardio M, Adamo F et al (1991) octanamide, Octanohydroxamic Acid, PhenostatTM Multiple sensitization due to CAS Registry Number [7377-03-9] bis-dithiocarbamate and thiophthalimide pesti- This preservative has been used in replacement cides. Contact Dermatitis 25:327 of parabens in moisturizers and has been associ- ated with an epidemic of allergic contact dermati- tis in Finland. 85 Captan

Captane, N-Trichloromethylmercaptotetrahy- drophtalimide CAS Registry Number [133-06-2] A pesticide, belonging to the thiophthalimide group, mainly affects agricultural workers. Being sensitizer and photosensitizer, it can induce con- 83.1 Suggested Reading tact urticaria. It is used as a fungicide and a bac- teriostatic agent in cosmetics and toiletries, Ackermann L, Virtanen H, Korhonen L et al particularly in shampoos. Cases of contact derma- (2017) An epidemic of allergic contact derma- titis were reported in painters, polishers, and titis caused by a new allergen, caprylhy- varnishers. droxamic acid, in moisturizers. Contact – Dermatitis 77:159 162 O

84 Captafol N S CI CAS Registry Number [2425-06-1] CI Captafol is a pesticide, belonging to O CI thiophthalimide group. Occupational contact der- matitis was reported in an agricultural worker who had multiple sensitizations. 85.1 Suggested Reading

O Aguirre A, Manzano D, Zabala R et al (1994) Contact allergy to captan in a hairdresser. Con- tact Dermatitis 31:46 N S Moura C, Dias M, Vale T (1994) Contact derma- titis in painters, polishers and varnishers. Con- CHCI2 CI tact Dermatitis 31:51–53 O CI O’Malley M, Rodriguez P, Maibach HI (1995) Pesticide patch testing: California nursery workers and controls. Contact Dermatitis 32:61–62 60 J.-P. Lepoittevin and C. J. Le Coz

Peluso AM, Tardio M, Adamo F et al (1991) Mul- 87.1 Suggested Reading tiple sensitization due to bis-dithiocarbamate and thiophthalimide pesticides. Contact Derma- Goday Bujan JJ, Yanguas Bayona I, Arechavala titis 25:327 RS (1994) Allergic contact dermatitis from Vilaplana J, Romaguera C (1993) Captan, a rare cyanamide: report of 3 cases. Contact Derma- contact sensitizer in hairdressing. Contact Der- titis 31:331–332 matitis 29:107

88 Carbofuran 86 Carbaryl CAS Registry Number [1563-66-2] CAS Registry Number [63-25-2] It is a pesticide with insecticide properties, of Carbaryl is a pesticide and insecticide of the the group. It was implicated as a sensi- carbonate group. It induced sensitization in a tizer in two farmers. farmer. O O

O N O N H O H

88.1 Suggested Reading 86.1 Suggested Reading Sharma VK, Kaur S (1990) Contact sensitization Sharma VK, Kaur S (1990) Contact sensitization by pesticides in farmers. Contact Dermatitis by pesticides in farmers. Contact Dermatitis 23:77–80 23:77–80

89 Cardols 87 Carbodiimide Cardols are a mixture of several analog molecules Cyanamide with an alkyl chain (-R) with 13, 15, 17, or 19 car- CAS Registry Number [420-04-2] bon and 0–3 unsaturations. It is one of the main Cyanamide and its salts are used in various cashew nut shell liquid components, along with occasions such as in chemistry, in anti-rust solu- anacardic acid. Sensitization occurs in cashew nut tions, or in a drug (Come®) for treating alcoholism workers. (inhibition of alcohol dehydrogenase). OH H N CN

H HO R Dictionary of Contact Allergens: Chemical Structures, Sources, and References 61

89.1 Suggested Reading H O N Diogenes MJN, De Morais SM, Carvalho FF (1996) Contact dermatitis among cashew nut workers. Contact Dermatitis 35:114–115 OH H O N 90 D-3-Carene

CAS Registry Number [13466-78-9] Hydroperoxides of Δ-3-carene are allergens 91.1 Suggested Reading contained in turpentine. Occupational exposure occurs in painters, varnishers, or ceramic decora- Giordano-Labadie F, Lepoittevin JP, Calix I et al tion. The percentage of Δ-3-carene is higher in (1997) Allergie de contact aux ^a-bloqueurs des Indonesian than in Portuguese turpentine. collyres: allergie croisée? Ann Dermatol Venereol 124:322–324 Nino M, Balato A, Ayala F et al (2007) Allergic contact dermatitis due to levobunolol with cross-sensitivity to befunolol. Contact Derma- titis 56:53–54

92 CD1

N,N-Diethylparaphenylenediamine Monochlorhy- 90.1 Suggested Reading drate CAS Registry Number [2198-58-5] Lear JT, Heagerty AHM, Tan BB et al (1996) A color film developer. It is an allergen and an Transient re-emergence of oil turpentine irritant in photographers. Cross-reactivity is pos- allergy in the pottery industry. Contact Derma- sible with Disperse Blue 124, Disperse Blue titis 35:169–172 106, and Disperse red 17, but not with para- amino compounds.

91 Carteolol N CAS Registry Number [51781-06-7] Carteolol was implicated in allergic contact HCI dermatitis due to beta-blocker agents in eyedrops. It seems that this molecule can be safely used in some patients with hypersensitivity to other topi- NH cal beta-blocker agents. 2 62 J.-P. Lepoittevin and C. J. Le Coz

92.1 Suggested Reading developers: absence of cross-sensitivity to para-amino compounds. Contact Dermatitis Aguirre A, Landa N, Gonzalez M et al (1992) 30:301 Allergic contact dermatitis in a photographer. Lidén C, Brehmer-Andersson E (1988) Occupa- Contact Dermatitis 27:340–341 tional dermatoses from colour developing Galindo PA, Garcia R, Garrido JA et al (1994) agents. Clinical and histopathological observa- Allergic contact dermatitis from colour devel- tions. Acta Derm Venereol (Stockh) opers: absence of cross-sensitivity to para- 68:514–522 amino compounds. Contact Dermatitis 30:301 Rustemeyer T, Frosch PJ (1995) Allergic contact Lidén C, Brehmer-Andersson E (1988) Occupa- dermatitis from colour film developers. Con- tional dermatoses from colour developing tact Dermatitis 32:59–60 agents. Clinical and histopathological observa- tions. Acta Derm Venereol (Stockh) 68:514–522 94 CD3

4-(Ethyl-N-2-methane-sulfonamidoethyl)-2-me- 93 CD2 thyl-1,4-phenylenediamine ( 1,5H2SO4 H2O) CAS Registry Number [25646-71-3] 4-N,N-Diethyl-2-methyl-1,4-phenylenediamine A color film developer. It caused some allergic (Hydrochloride) reactions in photographers. Cross-reactivity is CAS Registry Number [2051-79-8] possible with Disperse Blue 124, Disperse Blue A color film developer. It acts as an allergen 106, and Disperse Red 17. and an irritant in photographers. Cross-reactivity is possible with Disperse Blue 124, Disperse Blue H 106, and Disperse Red 17, but not to para-amino N compounds. S N O O N H2SO4

HCI NH2

NH 2 94.1 Suggested Reading

93.1 Suggested Reading Aguirre A, Landa N, Gonzalez M et al (1992) Allergic contact dermatitis in a photographer. – Aguirre A, Landa N, Gonzalez M et al (1992) Contact Dermatitis 27:340 341 Allergic contact dermatitis in a photographer. Galindo PA, Garcia R, Garrido JA et al (1994) Contact Dermatitis 27:340–341 Allergic contact dermatitis from colour devel- Galindo PA, Garcia R, Garrido JA et al (1994) opers: absence of cross-sensitivity to para- Allergic contact dermatitis from colour amino compounds. Contact Dermatitis 30:301 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 63

Lidén C, Brehmer-Andersson E (1988) Occupa- Rustemeyer T, Frosch PJ (1995) Allergic contact tional dermatoses from colour developing dermatitis from colour developers. Contact agents. Clinical and histopathological observa- Dermatitis 32:59–60 tions. Acta Derm Venereol (Stockh) Scheman AJ, Katta R (1997) Photographic aller- 68:514–522 gens: an update. Contact Dermatitis 37:130 Rustemeyer T, Frosch PJ (1995) Allergic contact dermatitis from colour developers. Contact Dermatitis 32:59–60 96 CD6 Scheman AJ, Katta R (1997) Photographic aller- gens: an update. Contact Dermatitis 37:130 4-Amino-N-ethyl-N-(2-methoxyethyl)-2-methyl Paraphenylenediamine di-p-Toluene Sulfonate CAS Registry Number [50928-80-8] 95 CD4 This color film developer rarely induced con- tact dermatitis in photographers. 4-(Ethyl-N-hydroxyethyl)-2-methyl-1,4-pheny- lenediamine ( H2SO4 H2O) OCH3 CAS Registry Number [25646-77-9] N SO3H Color film developer. It is both an allergen and an irritant in photographers. Cross-reactivity is possible with Disperse Blue 124, Disperse Blue 2 106, and Disperse Red 17.

OH NH2 N

96.1 Suggested Reading

H2SO4 Lidén C (1989) Occupational dermatoses at a film laboratory. Contact Dermatitis 20:191–200

NH2 Lidén C, Brehmer-Andersson E (1988) Occupa- tional dermatoses from color developing agents. Clinical and histopathological observa- 95.1 Suggested Reading tions. Acta Derm Venereol (Stockh) 68:514–522 Aguirre A, Landa N, Gonzalez M et al (1992) Allergic contact dermatitis in a photographer. Contact Dermatitis 27:340–341 97 Cefaclor Galindo PA, Garcia R, Garrido JA et al (1994) Allergic contact dermatitis from colour devel- CAS Registry Number [70356-03-5] opers: absence of cross-sensitivity to para- Cefaclor is a semisynthetic cephalosporin anti- amino compounds. Contact Dermatitis 30:301 biotic, related to cefalexin, and a frequent inducer Lidén C, Brehmer-Andersson E (1988) Occupa- of serum sickness-like reactions. tional dermatoses from colour developing agents. Clinical and histopathological observa- tions. Acta Derm Venereol (Stockh) 68:514–522 64 J.-P. Lepoittevin and C. J. Le Coz

in three cases and to cefuroxime in one case with O cross-reaction to cephalotin and cephaloridine. HH S N H H H2O R1 NH2 N N S O CI COOH O N 2 O R 97.1 Suggested Reading COOH

Hebert AA, Sigman ES, Levy ML (1991) Serum sickness-like reactions from cefaclor in chil- 98.1 Suggested Reading dren. J Am Acad Dermatol 25:805–808 Filipe P, Soares Almeida RSL et al (1996) Occu- pational allergic contact dermatitis from ceph- 98 Cephalosporins alosporins. Contact Dermatitis 34:226 Foti C, Vena GA, Cucurachi MR et al (1994) All cephalosporins have a 7-amino- Occupational contact allergy from cephalospo- cephalosporanic group (cephem nucleus). They rins. Contact Dermatitis 31:129–130 differ by a C7 and a C3 substitution. The cause of Garcia-Bravo B, Gines E, Russo F (1995) Occu- an allergic reaction to cephalosporins can be the pational contact dermatitis from ceftiofur cephem nucleus itself, but this seems to be rare. sodium. Contact Dermatitis 33:62–63 Allergic contact dermatitis from cephalosporins is Romano A, Pietrantonio F, Di Fonso M et al uncommon and mainly occurs in health care, (1992) Delayed hypersensitivity to pharmaceutical, and veterinary professions. Sys- cefuroxime. Contact Dermatitis 27:270–271 temic drug reactions are more frequent and can involve an immuno-allergic mechanism or not. Some of them are severe and life threatening. 99 Cetearyl Isononanoate Cefaclor is frequently responsible for serum thickness diseases. Cefotaxime, ceftizoxime, Cetearyl Hexadecyl Isononanoate ceftazidime, ceftriaxone, and cefodizime, several CAS Registry Number [84878-33-1] third-generation cephalosporins, caused positive This substance results from esterification of a patch reactions in a sensitized nurse. Cefazoline, saturated C16–C18 alcohol, namely, cetyl or cefoxitin, ceftriaxone, and ceftazidime were , and a branched chain isononanoic responsible for contact dermatitis in a nurse. Sen- acid. It is used as a hair conditioning agent, a skin sitivity to cephalothin, cephamandol, and conditioning agent, and an emollient, and is found cephazolin, cephalosporins of the first and second in several moisturizing creams. generation, was reported in a pharmaceutical lab- oratory analyst. Ceftiofur sodium, a third- O generation veterinary cephalosporin, caused con- O tact dermatitis in two chicken vaccinators. No n cross-sensitivity was observed to other cephalo- n: 14 to 16 sporins. Cephalexin hypersensitivity was reported Dictionary of Contact Allergens: Chemical Structures, Sources, and References 65

99.1 Suggested Reading repeated applications in health workers, leg ulcer, and leg eczema patients. Immediate-type Le Coz CJ, Bressieux A (2003) Allergic contact reactions have been reported: contact urticaria, dermatitis from cetearyl isononanoate. Contact asthma, and anaphylactic shock. Dermatitis 48:343 Sarre M-E, Mancel E, Drouet M et al (2017) H H H H H H Allergic contact dermatitis caused by cetearyl N N N N N N isononanoate in a sunscreen product. Contact 6 NH NH NH NH Dermatitis 76:357–358 CI CI

OH OH

100 Chloramphenicol HOOC OH OH OH 2 CAS Registry Number [56-75-7] This broad-spectrum phenicol group antibiotic 101.1 Suggested Reading has been implicated in allergic contact dermatitis. Cross-sensitivity to thiamphenicol is possible, but Aalto-Korte K, Mäkinen-Kiljunen S (2006) not systematic. Symptoms of immediate chlorhexidine hyper- sensitivity in patients with a positive prick test. OH CI Contact Dermatitis 55:173–177 H N Krautheim AB, Jermann THM, Bircher AJ (2004) CI Chlorhexidine anaphylaxis: case report and review of the literature. Contact Dermatitis O 50:113–116 O N OH 2 Rudzki E, Rebandel P, Grzywa Z (1989) Patch tests with occupational contactants in nurses, 100.1 Suggested Reading doctors and dentists. Contact Dermatitis 20:247–250 Le Coz CJ, Santinelli F (2007) Facial contact dermatitis from chloramphenicol with cross- sensitivity to thiamphenicol. Contact Dermati- 102 5-Chloro-1-Methyl-4- tis 38:108–109 Nitroimidazole

CAS Registry Number [4897-25-0] 101 Chlorhexidine (Digluconate) This intermediate in azathioprine synthesis is also present in the end product. It induced contact CAS Registry Number [55-56-1] (CAS Registry dermatitis in a man working on azathioprine syn- thesis. Cross-reactivity is possible with imidaz- Number [18472-51-0]) oles, tioconazole, and econazole. Chlorhexidine is a broad-spectrum antimicro- bial agent, a synthetic biguanide antiseptic, and disinfectant, available under different forms CI N (diacetate, dihydrochloride, and mostly digluconate). It is also used as a biocide in several topicals and cosmetics. It may cause allergic con- N O N tact dermatitis, photosensitivity, or even fixed 2 drug eruption, mainly after prolonged and 66 J.-P. Lepoittevin and C. J. Le Coz

102.1 Suggested Reading 104.1 Suggested Reading

Jolanki R, Alanko K, Pfäffli P et al (1997) Occu- Brand CU, Schmidli J, Ballmer-Weber B et al pational allergic contact dermatitis from (1995) Lymphozytenstimulationstest, eine 5-chloro-1-methyl-4-nitroimidazole. Contact mögliche Alternative zur Sicherung einer Dermatitis 36:53–54 Cloracetophenon-Sensibilisierung. Hautarzt 46:702–704

103 Chloroacetamide 105 Chloroatranol CAS Registry Number [79-07-2] Chloroacetamide as a preservative is used in CAS Registry Number [57074-21-2] several applications as in cutting metalworking Chloroatranol has been identified as a constit- fluids, in paints, or in glues. It can induce contact uent and major allergen in oak-moss absolute, a dermatitis in hairdressers or in shoemakers, being frequent allergen in people sensitized to perfumes. used as a leather preservative. This potent allergen gives reactions with concen- trations down to 5 ppm in sensitized patients. It O may cross-react with atranol.

CI NH2 CI 103.1 Suggested Reading

Katsarou A, Koufou B, Takou K et al (1995) Patch HO OH test results in hairdressers with contact derma- – titis in Greece (1985 1994). Contact Dermati- O tis 33:347–348 Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. Con- 105.1 Suggested Reading tact Dermatitis 34:17–22 Andersen F, Andersen KH, Bernois A et al (2015) Reduced content of chloroatranol and atranol 104 Chloroacetophenone in oak moss absolute significantly reduces the elicitation potential of this fragrance material. CAS Registry Number [532-27-4] Contact Dermatitis 72:75–83 ω-Chloroacetophenone is contained in tear Bernard G, Giménez-Arnau E, Rastogi SC et al gases (lacrimators). This substance has important (2003) Contact allergy to oak moss: search for irritative potential but can also be a sensitizer. sensitizing molecules using combined bioassay-guided chemical fractionation, O GC-MS and structure-activity relationship analysis (part 1). Arch Dermatol Res CI 295:229–235 Johansen JD, Andersen KE, Svedman C et al (2003) Chloroatranol, an extremely potent allergen hidden in perfumes: a dose response Dictionary of Contact Allergens: Chemical Structures, Sources, and References 67

elicitation study. Contact Dermatitis 107.1 Suggested Reading 49:180–184 Lamminpää A, Estlander T, Jolanki R et al (1996) Occupational allergic contact dermatitis 106 Chlorocresol caused by decorative plants. Contact Dermati- tis 34:330–335 4-Chloro-3-methylphenol, Parachlorometacresol, 2-Chloro-5-hydroxytoluene CAS Registry Number [59-50-7] 108 Chlorothalonil Chlorocresol is a biocide used for its disinfec- tant and preservative properties, in topicals or 2,4,5,6–1,3-Tetrachloroisophtalonitrile, 1,3-Dicyano cutting fluid. Tetrachlorobenzene, Daconil® CAS Registry Number [1897-45-6] CI Chlorothalonil is a fungicide widely used in the cultivation of ornamental plants and flowers, rice, and onions. In banana plantations it is used in HO fumigations by airplanes. It can be used as a preservative of paints and woods. It can induce contact urticaria, irritant and allergic contact der- 106.1 Suggested Reading matitis, erythema dyschromicum perstans, or fol- liculitis mainly in agricultural workers, wood- Le Coz CJ, Scrivener Y, Santinelli F et al (1998) related professions, or in horticulturists. Sensibilisation de contact au cours des ulcères de jambe. Ann Dermatol Venereol CN 125:694–699 CI Walker SL, Chalmers RJ, Beck MH (2004) Con- CI tact urticaria due to p-chloro- m-cresol. Br J Dermatol 151:936–937 CI CN

CI 107 Chlorophorin

CAS Registry Number [537-41-7] 108.1 Suggested Reading Chlorophorin is the allergen in iroko, kambala (Chlorophora excelsa). Occupational dermatitis Boman A, Montelius J, Rissanen RL et al (2000) can occur in woodworkers. Sensitizing potential of chlorothalonil in the guinea pig and the mouse. Contact Dermatitis HO OH 43:273–279 Meding B (1986) Contact dermatitis from tetra- OH chloroisophthalonitrile in paint. Contact Der- matitis 15:187 O’Malley M, Rodriguez P, Maibach HI (1995) OH Pesticide patch testing: California nursery workers and controls. Contact Dermatitis 32:61–62 Penagos H, Jimenez V, Fallas V et al (1996) Chlorothalonil, a possible cause of erythema 68 J.-P. Lepoittevin and C. J. Le Coz

dyschromicum perstans (ashy dermatosis). Contact Dermatitis 35:214–218 O

109 Chlorpromazine H

CAS Registry Number [50-53-3] This phenothiazine with sedative properties is 110.1 Suggested Reading used in human medicine and induced contact der- matitis in nurses or those working in the pharma- Nethercott JR, Holness DL (1989) Occupational ceutical industry. It is also used in veterinary dermatitis in food handlers and bakers. J Am medicine to avoid mortality of pigs during trans- Acad Dermatol 21:485–490 portation. It is a sensitizer and a photosensitizer. Seite-Bellezza D, El Sayed F, Bazex J (1994) Contact urticaria from cinnamic aldehyde and benzaldehyde in a confectioner. Contact Der- N matitis 31:272–273

111 Cinnamyl Alcohol

N CI Cinnamic Alcohol, 3-Phenyl-2-propenol CAS Registry Number [104-54-1] Cinnamyl alcohol occurs (in esterified form) in S storax, Myroxylon pereirae, cinnamon leaves, and hyacinth oil. It is obtained by the alkaline hydro- lysis of storax and prepared synthetically by 109.1 Suggested Reading reducing cinnamal diacetate with iron filings and acetic acid and from by Brasch J, Hessler HJ, Christophers E (1991) Meerwein-Ponndorf-Verley reduction with alumi- Occupational (photo)allergic contact dermati- num isopropoxide. Cinnamic alcohol is contained tis from azaperone in a piglet dealer. Contact in the “fragrance mix.” As a fragrance allergen, it Dermatitis 25:258–259 has to be mentioned by name in cosmetics within the EU. Occupational cases of contact dermatitis were reported in perfume industry. Patch tests can 110 Cinnamal be positive in food handlers. Cinnamic Aldehyde, Cinnamaldehyde, 3-Phenyl- 2-propenal CAS Registry Number [104-55-2] OH This perfumed molecule is used as a fragrance in perfumes, a flavoring agent in soft drinks, ice creams, dentifrices, pastries, chewing gum, etc. It can induce both contact urticaria and delayed-type 111.1 Suggested Reading reactions. It can be responsible for dermatitis in the perfume industry or in food handlers. Gutman SG, Somov BA (1968) Allergic reactions Cinnamic aldehyde is contained in “fragrance caused by components of perfumery prepara- mix.” As a fragrance allergen, it has to be men- tions. Vestn Dermatol Venereol 12:62–66 tioned by name in cosmetics within the EU. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 69

Nethercott JR, Holness DL (1989) Occupational 113 Citronellol dermatitis in food handlers and bakers. J Am Acad Dermatol 21:485–490 3,7-Dimethyl-6-octen-1-ol, Cephrol CAS Registry Numbers [106-22-9] and [26489-01-0] 112 Citral l-Citronellol is a constituent of rose and gera- nium oils. d-Citronellol occurs in Ceylon and Java 3,7-Dimethyl-2,6-octadien-1-al, Blend of Neral citronella oils. As a fragrance allergen, citronellol and Geranial, Blend of (Z)-3,7-Dimethyl-2,6- has to be mentioned by name in cosmetics within octadienal, and (E)-3,7-Dimethyl-2,6-octadienal the EU. CAS Registry Number [5392-40-5] (CAS Registry Number [141-27-5] + CAS Registry Number [106-26-3]) Citral is an aldehyde fragrance and flavoring ingredient, a blend of isomers cis (Neral) and trans (geranial). As a fragrance allergen, citral OH has to be mentioned by name in cosmetics within the EU.

113.1 Suggested Reading O Frosch PJ, Johansen JD, Menné T et al (2002) O Further important sensitizers in patients sensi- tive to fragrances. Contact Dermatitis 47:78–85 Rudbaäck J, Hagvall L, Börje A et al (2014) Neral Geranial Characterization of skin sensitizers from auto- xidized citronellol – impact of the terpene structure on the autoxidation process. Contact 112.1 Suggested Reading Dermatitis 70:329–339 Frosch PJ, Johansen JD, Menné T et al (2002) Further important sensitizers in patients sensi- 114 Clindamycin tive to fragrances. Contact Dermatitis 47:78–85 Clindamycin: CAS Registry Number [18323-44-9] De Mozzi P, Johnston GA (2014) A outbreak of Clindamycin Hydrochloride: CAS Registry allergic contact dermatitis caused by sitral in Number [21462-39-5] beauticians working in a health spa. Contact Clindamycin Phosphate: CAS Registry Num- Dermatitis 70:377–379 ber [24729-96-2] This lincosanide antibiotic used in topical form for acne or systemically has been responsible for exanthematous rashes and acute generalized exan- thematous pustulosis. 70 J.-P. Lepoittevin and C. J. Le Coz

H CH3 by liquid chromatography: collaborative study. H C CH3 O N – 3 N Cl J AOAC Int 86:685 693 OH O OH S CH OH 3 116 Cloxacillin

CAS Registry Number [61-72-3] 114.1 Suggested Reading Cloxacillin Sodium Monohydrate: CAS Reg- istry Number [7081-44-9] Lammintausta K, Tokola R, Kalimo K (2002) Cloxacillin is a semisynthetic penicillin close Cutaneous adverse reactions to clindamycin: to oxacillin. It induced contact dermatitis in a results of skin tests and oral exposure. Br J pharmaceutical factory worker with positive reac- Dermatol 146:643–648 tions to ampicillin, but not to penicillin. In cuta- Papakonstantinou E, Müller S, Röhrbein JH et al neous drug reactions such as acute generalized (2018) Generalized reactions during skin test- exanthematous pustulosis due to amoxicillin, ing with clindamycin in drug hypersensitivity: cross-reactivity is frequent to cloxacillin (personal a report of 3 cases and review of the literature. observations). Contact Dermatitis 78:274–280 Valois M, Phillips EJ, Shear NH et al (2003) Clindamycin-associated acute generalized CI exanthematous pustulosis. Contact Dermatitis 48:169 N O O 115 Clopidol N S H Methylchlorpindol, 3,5-Dichloro-2,6-dimethyl-4- N pyridinol O COOH CAS Registry Number [2971-90-6], [11116- 46-4], and [68821-99-8] This drug is used for the prevention of coccid- 116.1 Suggested Reading iosis in poultry. Rudzki E, Rebandel P (1991) Hypersensitivity to N semisynthetic penicillins but not to natural penicillin. Contact Dermatitis 25:192

CI CI

OH 117 Cobalt Naphthenate

Naphthenic Acids, Cobalt Salts 115.1 Suggested Reading CAS Registry Numbers [61789-51-3] and [161279-65-8] Mancuso G, Staffa M, Errani A et al (1990) Occu- Cobalt naphthenate is made by treating cobalt pational dermatitis in animal feed mill workers. hydroxide or acetate with naphthenic acid. It is an Contact Dermatitis 22:37–41 accelerant in rubber, unsaturated polyester, and Pang GF, Cao YZ, Fan CL et al (2003) Determi- vinyl ester resins. nation of clopidol residues in chicken tissues Dictionary of Contact Allergens: Chemical Structures, Sources, and References 71

117.1 Suggested Reading 118.1 Suggested Reading

Shena D, Rosina P, Chieregato C et al (1995) Angelini G, Foti C, Rigano L et al (1995) Lymphomatoid-like contact dermatitis from 3-Dimethylaminopropylamine: a key substance cobalt naphthenate. Contact Dermatitis in contact allergy to cocamidopropylbetaine? 33:197–198 Contact Dermatitis 32:96–99 Tarvainen K, Jolanki R, Forsman-Gronholm L De Groot AC, van der Walle HB, Weyland JW et al (1993) Exposure, skin protection and (1995) Contact allergy to cocamidopropyl occupational skin diseases in the glass-fibre- betaine. Contact Dermatitis 33:419–422 reinforced plastics industry. Contact Dermati- McFadden JP, Ross JS, White IR et al (2001) tis 29:119–127 Clinical allergy to cocamidopropyl betaine: reactivity to cocamidopropylamine and lack of reactivity to 3-dimethylaminopropylamine. 118 Cocamidopropyl Betaine Contact Dermatitis 45:72–74

Cocoamphodipropionate, Cocamidopropyl Dimethyl Glycine, Cocoamphocarboxypropionate, Cocoyl 119 Cocamidopropyl Amide Propylbetaine, N-(2-Aminoethyl)- N- Dimethylamine [2-(2-carboxyethoxy)ethyl] beta-Alanine CAS Registry Numbers [61789-40-0], [83138- N-[3-(Dimethylamino)propyl]coco Amides, 1-(N, 08-3], and [86438-79-1] N-Dimethylamino)-3-(Coconut Oil Amido)- Cocamidopropyl betaine is a pseudo-amphoteric Propane, Coconut Fatty Acid, zwitterion detergent derived from long-chain Dimethylaminopropylamide alkylbetaines. It is available from many suppliers CAS Registry Number [68140-01-2] under more than 50 trade names (including Tego- This amido amine may be the allergen in betain L7 and Ampholyt JB 130). Exposure occurs cocamidopropyl betaine. via rinse-off products such as liquid soaps, shampoos, and shower gels but also via leave-on products (e.g., H roll-on deodorant). Occupational sources are mainly R NN in hairdressing. The first synthesis step consists of the reaction of coconut fatty acids with 3- O dimethylaminopropylamine, giving cocamidopropyl dimethylamine. This amido amine is converted into cocamidopropyl betaine by reaction with sodium 119.1 Suggested Reading monochloroacetate. Both dimethylaminopropyla- mine and cocamidopropyl dimethylamine are McFadden JP, Ross JS, White IR et al (2001) thought to be the sensitizers. Clinical allergy to cocamidopropyl betaine: reactivity to cocamidopropylamine and lack of reactivity to 3-dimethylaminopropylamine. H Contact Dermatitis 45:72–74 R N N COO

O 120 Coconut Diethanolamide

Cocamide DEA, Coconut Oil Fatty Acids Diethanolamide, N,N-bis(2-Hydroxyethyl)Coco Fatty Acid Diethanolamide, Cocoyl Diethanolamide 72 J.-P. Lepoittevin and C. J. Le Coz

CAS Registry Number [68603-42-9] O Cocamide DEA, manufactured from coconut oil, is widely used in industry and at home as a surface-active agent. It is contained in hand gels, handwashing soaps, shampoos, and dishwashing O H liquids for its foam-producing and foam- N stabilizing properties and in metalworking fluids and polishing agents as an anticorrosion inhibitor. HO

OH 121.1 Suggested Reading

R N Condé-Salazar L, Guimaraens D, Gonzalez M OH et al (1991) Occupational allergic contact der- matitis from opium alkaloids. Contact Derma- O titis 25:202–203 Estrada JL, Alvarez Puebla MJ, Ortiz de Urbina JJ 120.1 Suggested Reading et al (2001) Generalized eczema due to codeine. Contact Dermatitis 44:185 Fowler JF Jr (1998) Allergy to cocamide DEA. Waclawski ER, Aldridge R (1995) Occupational Am J Contact Dermat 9:40–41 dermatitis from thebaine and codeine. Contact Kanerva L, Jolanki R, Estlander T (1993) Den- Dermatitis 33:51 tist’s occupational allergic contact dermatitis caused by coconut diethanolamide, N-ethyl-4- toluene sulfonamide and 122 Costunolide 4-tolydietahnolamine. Acta Derm Venereol (Stockh) 73:126–129 CAS Registry Number [553-21-9] Pinola A, Estlander T, Jolanki R et al (1993) This germacranolide sesquiterpene lactone is Occupational allergic contact dermatitis due extracted from costus oil. With alantolactone and to coconut diethanolamide (Cocamide DEA). dehydrocostunolide, it is a component of lactone Contact Dermatitis 29:262–265 mix used to elicit reactions in patients sensitive to Asteraceae-Compositae. An erythema-multiform- like occupational contact dermatitis case occurred 121 Codeine (Phosphate, in a chemical student after an accidental exposure Hydrochloride) to costus oil.

Methylmorphine CAS Registry Number [76-57-3] (CAS Regis- try Number [52-28-8], CAS Registry Number [1422-07-7]) Codeine has been reported as an occupational O sensitizer in workers in the production of opium O alkaloids. Codeine has been responsible for fixed drug eruptions or generalized dermatitis. Cross- sensitivity is expected to morphine. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 73

122.1 Suggested Reading 124 Cresyl Glycidyl Ether

Ducombs G, Benezra C, Talaga P et al (1990) CAS Registry Number [26447-14-3] Patch testing with the “sesquiterpene lactone It is a reactive diluent added in epoxy resins mix”: a marker for contact allergy to bisphenol A type. Compositae and other sesquiterpene-lactone- containing plants. Contact Dermatitis O 22:249–252 O Le Coz CJ, Lepoittevin JP (2001) Occupational CH3 erythema-multiforme-like dermatitis from sen- sitization to costus resinoid, followed by flare- up and systemic contact dermatitis from beta- cyclocostunolide in a chemistry student. Con- 124.1 Suggested Reading tact Dermatitis 44:310–311 Chieregato C, Vincenzi C, Guerra L et al (1994) Occupational allergic contact dermatitis due to 123 Coumarin ethylenediamine dihydrochloride and cresyl glycidyl ether in epoxy resin systems. Contact 1-Benzopyran-2-one, cis-o-Coumarinic Acid Dermatitis 30:120 Lactone Daecke C, Schaller J, Goos M (1994) Acrylates as CAS Registry Number [91-64-5] potent allergens in occupational and domestic Coumarin is an aromatic lactone naturally exposures. Contact Dermatitis 30:190–191 occurring in tonka beans and other plants. As a Holness DL, Nethercott JR (1993) The perfor- fragrance allergen, it has to be mentioned by name mance of specialized collections of bisphenol in cosmetics within the EU. A epoxy resin system components in the eval- uation of workers in an occupational health O O clinic population. Contact Dermatitis 28:216–219 Jolanki R, Kanerva L, Estlander T et al (1990) Occupational dermatoses from epoxy resin compounds. Contact Dermatitis 23:172–183 123.1 Suggested Reading

Frosch PJ, Johansen JD, Menné T et al (2002) 125 Cyclohexanone Further important sensitizers in patients sensi- CAS Registry Number [108-94-1] tive to fragrances. Contact Dermatitis Used as a polyvinyl chloride solvent, cyclo- 47:78–85 hexanone caused contact dermatitis in a woman Mutterer V, Giménez-Arnau E, Lepoittevin J-P manufacturing PVC fluidotherapy bags. Cyclo- et al (1999) Identification of coumarin as the hexanone probably does not cross-react with sensitizer in a patient sensitive to her own cyclohexanone resin. A cyclohexanone-derived perfume but negative to the fragrance mix. resin used in paints and varnishes caused contact Contact Dermatitis 40:196–199 dermatitis in painters. 74 J.-P. Lepoittevin and C. J. Le Coz

O N S

S N

H

125.1 Suggested Reading 127.1 Suggested Reading

Bruze M, Boman A, Bergquist-Karlson A et al Condé-Salazar L, Del-Rio E, Guimaraens D et al (1988) Contact allergy to cyclohexanone resin (1993) Type IV allergy to rubber additives: a in humans and guinea pigs. Contact Dermatitis 10-year study of 686 cases. J Am Acad – 18:46–49 Dermatol 29:176 180 Sanmartin O, de la Cuadra J (1992) Occupational Kiec-Swierczynska M (1995) Occupational sen- contact dermatitis from cyclohexanone as a sitivity to rubber. Contact Dermatitis – PVC adhesive. Contact Dermatitis 27:189–190 32:171 172 Von Hintzenstern J, Heese A, Koch HU et al (1991) Frequency, spectrum and occupational 126 2-Cyclohexen-1-one relevance of type IV allergies to rubber chemicals. Contact Dermatitis 24:244–252 CAS Registry Number [930-68-7] This strong sensitizer has been responsible for N N p chemical burning followed by sensitization in a 128 -Cyclohexyl- -Phenyl- - chemistry student. Phenylenediamine

O N-Phenyl-N-cyclohexyl-p-phenylenediamine, CPPD CAS Registry Number [101-87-1] CPPD is a rubber chemical used as an antiox- idant. Cross-reactions are frequently observed with N-isopropyl-N-phenylparaphenyle- nediamine (IPPD). 126.1 Suggested Reading

Goossens A, Deschutter A (2003) Acute irritation followed by primary sensitization to H N 2-cyclohenen-1-one in a chemistry student. Contact Dermatitis 48:163–164

127 N-Cyclohexyl-2- Benzothiazylsulfenamide N H CAS Registry Number [95-33-0] A rubber accelerator chemical. The most fre- quent occupational categories are metal industry, homemakers, health services and laboratories, and the building industry. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 75

128.1 Suggested Reading 130 Cymene

Hervé-Bazin B, Gradiski D, Duprat P et al (1977) Cymol, Methyl-Isopropyl-Benzol Occupational eczema from N-isopropyl- N- CAS Registry Number [25155-15-1] phenylparaphenylenediamine (IPPD) and N- Terpenes, constitutive of essential oils, are

dimethyl-1,3 butyl- N-phenylparaphenyle- hydrocarbons with the general formula C10H16. nediamine (DMPPD) in tyres. Contact Derma- They are structurally related to cymol. titis 3:1–15 Von Hintzenstern J, Heese A, Koch HU et al (1991) Frequency, spectrum and occupational CH3 relevance of type IV allergies to rubber chemicals. Contact Dermatitis 24:244–252

129 N-(Cyclohexylthio)phthalimide

CAS Registry Number [17796-82-6] 130.1 Suggested Reading N-Cyclohexyl-thiophthalimide is a rubber chemical, widely used as a vulcanization retarder. Selvaag E, Holm JO, Thune P (1995) Allergic Sensitization sources are often protective gloves. contact dermatitis in an aroma therapist with multiple sensitizations to essential oils. Con- – S tact Dermatitis 33:354 355

N 131 Cymoxanil

2-Cyano-N-[(ethylamino)carbonyl]-2-(methoxyi- S mino)acetamide CAS Registry Number [57966-95-7] Cymoxanil, an urea derivative, is included 129.1 Suggested Reading (10%) with dithianone (25%) in Aktuan®.Itisa fungicide agent, possibly sensitizing agricultural Geier J, Lessmann H, Frosch PJ et al (2003) workers. Contact sensitization to N-(cyclohexylthio) phthalimide. Contact Dermatitis 48:1–6 O O Huygens S, Barbaud A, Goossens A (2001) Fre-

quency and relevance of positive patch tests to CN cyclohexylthiophthalimide, a new rubber aller- N N gen. Eur J Dermatol 11:443–445 H H Kanerva L, Estlander T, Jolanki R (1996) Allergic N patch test reactions caused by the rubber chem- O ical cyclohexyl thiophthalimide. Contact Der- matitis 34:23–26 76 J.-P. Lepoittevin and C. J. Le Coz

131.1 Suggested Reading 133.1 Suggested Reading

Koch P (1996) Occupational allergic contact der- Sharma VK, Kaur S (1990) Contact sensitization matitis and airborne contact dermatitis from by pesticides in farmers. Contact Dermatitis 5 fungicides in a vineyard worker. Cross- 23:77–80 reactions between fungicides of the dithiocar- bamate group? Contact Dermatitis 34:324–329 134 Decyl Glucoside

132 Dazomet CAS Registry Numbers [58846-77-8], [68515- 73-1], [141464-42-8], and [54549-25-6] 3,5-Dimethyltetrahydro-1,3,5(2H)thiadiazine-2- Decyl glucoside or decyl d-glucoside, also thione, DMTT named decyl-beta-d-glucopyranoside, belongs to CAS Registry Number [533-74-4] the alkyl glucosides family and is obtained by Dazomet is a biocide used to control bacterial condensation of the fatty alcohol decyl alcohol and fungal growth in a pulp and paper system and and a d-glucose polymer. This nonionic surfactant also in agriculture for soil disinfection. It is and cleansing agent has been widely used for contained in Busan 1058, Mylone, and Fungicide several years, due to its foaming power and good 974 (Crag™). Sensitization, rarely reported, tolerance in rinse-off products such as shampoos, occurred in a paper mill worker. hair dyes and colors, and soaps. Decyl glucoside is also employed in leave-on products such as S S no-rinsing cleansing milks, lotions, and several sunscreen agents and is contained as a stabilizing N N surfactant of organic microparticles in sunscreen agent Tinosorb® M.

OH OH 132.1 Suggested Reading O O HO O O Warin AP (1992) Allergic contact dermatitis from co – dazomet. Contact Dermatitis 26:135 136 HO OH HO OH CAS : 54549-25-6 CO : 1 to 3

133 DDT OH O O O OH Dichlorodiphenyltrichloroethane HO O CAS Registry Number [50-29-3] HO OH This insecticide was formerly reported as a HO OH sensitizer in farmers or agricultural workers. CAS : 68515-73-1

CCI 3 134.1 Suggested Reading

Blondeel A (2003) Contact allergy to the mild surfactant decylglucoside. Contact Dermatitis CI CI 49:304–305 Le Coz CJ, Meyer MT (2003) Contact allergy to decyl glucoside in antiseptic after body pierc- ing. Contact Dermatitis 48:279–280 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 77

135 Dehydrocostuslactone 136.1 Suggested Reading

CAS Registry Number [477-43-0] Lamminpää A, Estlander T, Jolanki R et al (1996) A guaianolide sesquiterpene lactone is extra- Occupational allergic contact dermatitis cted from costus oil. It is one of the components of caused by decorative plants. Contact Dermati- lactone mix, with costunolide and alantolactone, tis 34:330–335 used to detect Compositae-sensitive patients. Meding B, Ahman M, Karlberg AT (1996) Skin symptoms and contact allergy in woodwork teachers. Contact Dermatitis 34:185–190

137 Diallyl Disulfide

CAS Registry Number [2179-57-9] O Diallyl disulfide is one of the major allergens in garlic (Allium sativum) and onions. Among patients patch-test-positive to garlic, all 13 who O were tested had positive reactions to diallyl sulfide 5% pet. 135.1 Suggested Reading S S Ducombs G, Benezra C, Talaga P et al (1990) Patch testing with the “sesquiterpene lactone ” mix : a marker for contact allergy to 137.1 Suggested Reading Compositae and other sesquiterpene-lactone- containing plants. Contact Dermatitis Bruynzeel DP (1997) Bulb dermatitis. Dermato- – 22:249 252 logical problems in the flower bulb industries. Contact Dermatitis 37:70–77 Lamminpää A, Estlander T, Jolanki R et al (1996) 136 Deoxylapachol Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- CAS Registry Number [3568-90-9] tis 34:330–335 fi Deoxylapachol is the main allergen identi ed McFadden JP, White IR, Rycroft RJG (1992) in teak (Tectona grandis). Sensitization often con- Allergic contact dermatitis from garlic. Con- cerns people involved in woodwork. tact Dermatitis 27:333–334

O 138 Diaminodiphenylmethane

4,4-Diaminodiphenylmethane, 4,4-Methyle- nedianiline CAS Registry Number [107-77-9] O 4,4-Diaminodiphenylmethane is an aromatic diamine used as a curing agent in epoxy resins of the bisphenol A type and in the production of 78 J.-P. Lepoittevin and C. J. Le Coz plastics, isocyanates, adhesives, elastomers, poly- 139 Diammonium Hydrogen urethane (elastic and rigid foams, paints, lacquers, Phosphate adhesives, binding agents, synthetics rubbers, and elastomeric fibers), and butyl rubber. CAS Registry Number [7783-28-0] 4,4-Diaminodiphenylmethane is also a This flame retardant caused contact dermatitis by-product in azo dyes. It is also possibly formed in surgical personnel. It was due to excessive by hydrolysis of diphenylmethane-4,4- residual concentrations in surgical garbs. diisocyanate. O O 2 NH P 4 HO O

H2N NH2 139.1 Suggested Reading 138.1 Suggested Reading Belsito DV (1990) Contact dermatitis from diammonium hydrogen phosphate in surgical Bruynzeel DP, van der Wegen-Keijser MH (1993) garb. Contact Dermatitis 23:267–268 Contact dermatitis in a cast technician. Contact Dermatitis 28:193–194 Condé-Salazar L, Gonzalez de Domingo MA, 140 Diazodiethylaniline Chloride Guimaraens D (1994) Sensitization to epoxy resin systems in special flooring workers. Con- CAS Registry Number [148-90-3] tact Dermatitis 31:157–160 It is a well-known allergen in diazo copy paper. Holness DL, Nethercott JR (1993) The perfor- This product is allergenic until exposed to light mance of specialized collections of bisphenol and inactivated by UV radiations. A epoxy resin system components in the eval- uation of workers in an occupational health clinic population. Contact Dermatitis N 28:216–219 N Jolanki R, Kanerva L, Estlander T et al (1994) Concomitant sensitization to triglycidyl iso- CI cyanurate, diaminodiphenylmethane and N 2-hydroxyethyl methacrylate from silk-screen printing coatings in the manufacture of circuit boards. Contact Dermatitis 30:12–15 Mancuso G, Reggiani M, Berdondini RM (1996) 140.1 Suggested Reading Occupational dermatitis in shoemakers. Con- – tact Dermatitis 34:17 22 Pambor M, Poweleit H (1992) Allergic contact dermatitis due to diazo copy paper. Contact Dermatitis 26:131–132 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 79

141 Diazolidinyl Urea 142.1 Suggested Reading

CAS Registry Number [78491-02-8] Condé-Salazar L, Del-Rio E, Guimaraens D et al Diazolidinyl urea, a formaldehyde releaser, is (1993) Type IV allergy to rubber additives: a contained mainly in cosmetics and toiletries and 10-year study of 686 cases. J Am Acad can be found in barrier creams. Dermatol 29:176–180 Le Coz CJ (2004) Fiche d’éviction en cas ’ OH OH d hypersensibilité au mercaptobenzothiazole et au mercapto mix. Ann Dermatol Venereol H 131:846–848 N N O N Von Hintzenstern J, Heese A, Koch HU et al HO (1991) Frequency, spectrum and occupational N O relevance of type IV allergies to rubber O OH chemicals. Contact Dermatitis 24:244–252

141.1 Suggested Reading 143 Dibucaine (Hydrochloride)

Doi T, Kajimura K, Taguchi S (2011) The differ- Cincaine, Cinchocain(e), Percaine, Sovcaine ent decomposition properties of diazolidinyl CAS Registry Number [85-79-0] (CAS Regis- urea in cosmetics and patch test materials. try Number [61-12-1]) Contact Dermatitis 65:81–91 Dibucaine hydrochloride is an amide group Le Coz CJ (2005) Hypersensibilité à la local anesthetic that can induce allergic contact Diazolidinyl urée et à l’Imidazolidinyl urée. dermatitis. Ann Dermatol Venereol 132:587–588 Van Hecke E, Suys E (1994) Where next to look N O for formaldehyde? Contact Dermatitis 31:268 HCI 142 Dibenzothiazyl Disulfide N O N CAS Registry Number [120-78-5] H This rubber chemical of the mercaptoben- zothiazole group is used as a vulcanization accel- erant. The most frequent occupational categories 143.1 Suggested Reading are metal industry, homemakers, health services and laboratories, and the building industry. Erdmann SM, Sachs B, Merk HF (2001) Systemic contact dermatitis from cinchocaine. Contact N Dermatitis 44:260–261 S S Nakada T, Iijima M (2000) Allergic contact der- matitis from dibucaine hydrochloride. Contact S S Dermatitis 42:283 N 80 J.-P. Lepoittevin and C. J. Le Coz

Yamadori Y, Oiso N, Hirao et al (2009) Allergic H contact dermatitis from dibucaine hydrochlo- ride, chlorpheniramine maleate, and N S naphazoline hydrochloride in an over-the –counter topical antiseptic. Contact Dermatitis N 61:52–53 H

144 Dibutyl Phthalate 145.1 Suggested Reading Kanerva L, Estlander T, Jolanki R (1994) Occu- CAS Registry Number [84-74-2] pational allergic contact dermatitis caused by It is mainly used as a nonreactive epoxy thiourea compounds. Contact Dermatitis diluent. 31:242–248 Kiec-Swierczynska M (1995) Occupational sensi- O tivity to rubber. Contact Dermatitis 32:171–172 Schmid-Grendelmeier P, Elsner P (1995) Contact O dermatitis due to occupational dibutylthiourea O exposure: a case of phonecard dermatitis. Con- tact Dermatitis 32:308–309

O 146 4,5-Dichloro-2-N-Octyl-4- 144.1 Suggested Reading Isothiazolin-3-one

® Capon F, Cambie MP, Clinard F et al (1996) Kathon 930 CAS Registry Number [64359-81-5] Occupational contact dermatitis caused by ® computer mice. Contact Dermatitis 35:57–58 Irritant and sensitizer, Kathon 930 caused Chieregato C, Vincenzi C, Guerra L et al (1994) contact dermatitis in employees of a textile fi Occupational allergic contact dermatitis due to nishing factory. ethylenediamine dihydrochloride and cresyl glycidyl ether in epoxy resin systems. Contact O Dermatitis 30:120 CI N

145 Dibutylthiourea S CI 1,3-Dibutyl-2-thiourea CAS Registry Number [109-46-6] 146.1 Suggested Reading Dibutylthiourea is used in the vulcanization of rubber, in paints, and glue removers as an anti- Kawai K, Nagakawa M, Sasaki Y et al (1993) ® corrosive, and in phonecards as a component of Occupational contact dermatitis from Kathon – the thermocoating sprayed over the optically read 930. Contact Dermatitis 28:117 118 layer of the card. Cross-sensitivity to other thio- Umekoji A, Fukai K, Sowa-Osako J et al (2016) urea derivatives is possible. Allergic contact dermatitis caused by the preser- vative 4,5-dichloro-2-n-octyl-4-isothiazolin-3- one in black trousers. Contact Dermatitis 75:326–328 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 81

147 1,3-Dichloropropene 149 N,N-Dicyclohexyl-2- Benzothiazole Sulfenamide 1,3-Dichloro-1-prop(yl)ene, 1,3-Dichloro-2-prop (yl)ene, DD-95 CAS Registry Number [4979-32-2] CAS Registry Number [542-75-6] This substance is a rubber accelerator of the This nematocide is used as a soil fumigant mercaptobenzothiazole-sulfenamide group. prior to crop cultivation. Farmers and process operators employed at pesticide plants are mainly N exposed. S S N CI CI

147.1 Suggested Reading 149.1 Suggested Reading Bousema MT, Wiemer GR, van Joost T (1991) A Le Coz CJ (2004) Fiche d’éviction en cas classic case of sensitization to DD-95. Contact d’hypersensibilité au mercaptobenzothiazole Dermatitis 24:132 et au mercapto mix. Ann Dermatol Venereol Corazza M, Zinna G, Virgili A (2003) Allergic 131:846–848 contact dermatitis due to 1,3-dichloropropene soil fumigant. Contact Dermatitis 48:341–342 150 Dicyclohexyl Carbodiimide 148 Dichlorvos CAS Registry Number [538-75-0] Used in peptide chemistry as a coupling CAS Registry Number [62-73-7] reagent. It is both an irritant and a sensitizer and Cases of sensitization to this organophospho- has caused contact dermatitis in pharmacists and rus compound with several commercial names chemists. (Benfos, Brevinyl, Chlorvinphos, DDVP, Equigard, Fly fighte, Nogos, and Unifos) were occupationally seen in chrysanthemum growers, horticulturists, technicians, and a chemist. N C N

O O P CI O O CI 150.1 Suggested Reading

Poesen N, de Moor A, Busschots A et al (1995) 148.1 Suggested Reading Contact allergy to dicyclohexyl carbodiimide and diisopropyl carbodiimide. Contact Derma- Cleenewerck MB, Martin P (1990) Dermite de titis 32:368–369 contact au Dichlorvos. Rev Fr Allergol 30:38 Mathias CG (1983) Persistent contact dermatitis from the insecticide dichlorvos. Contact Der- matitis 9:217–218 82 J.-P. Lepoittevin and C. J. Le Coz

151 Didecyldimethylammonium H Chloride N Bardac-22 CAS Registry Number [7173-51-5] OH This quaternary ammonium compound is used HO as a detergent disinfectant in hospitals, as an algaecide in swimming pools, as a fungicide, 152.1 Suggested Reading and against termites in wood. We observed severe contact dermatitis in a slaughterhouse worker Blum A, Lischka G (1997) Allergic contact der- using a liquid soap containing this product (per- matitis from mono-, di- and triethanolamine. sonal observation). Immediate-type manifesta- Contact Dermatitis 36:166 tions like urticaria and dyspnea have been Mertens S, Gilissen L, Goossens A (2016) Aller- reported. gic contact dermatitis caused by cocamide diethanolamine. Contact Dermatitis 75:20–24

153 Diethyl Sebacate

N Cl Ethyl Sebacate, Diethyl Decanedioate CAS Registry Number [110-40-7] This emulsifier has rarely been reported as a sensitizing agent, mainly in topical treatments.

O O 151.1 Suggested Reading O O Dejobert Y, Martin P, Piette F et al (1997) Contact dermatitis from didecyldimethylammonium chloride and bis-(aminopropyl)-laurylamine 153.1 Suggested Reading in a detergent-disinfectant used in hospital. Contact Dermatitis 37:95–96 Klmura M, Kawada A (2007) Contact dermatitis Houtappel M, Bruijnzeel-Koomen CA, due to diethyl sebacate. Contact Dermatitis – Röckmann H (2008) Immediate-type allergy 40:48 49 by occupational exposure to didecyl dimethyl Tanaka M, Kobayashi S, Murata T et al (2000) ammonium chloride. Contact Dermatitis Allergic contact dermatitis from diethyl 59:116–117 sebacate in lanoconazole cream. Contact Der- matitis 43:233–234

152 Diethanolamine 154 Diethyleneglycol Diglycidyl CAS Registry Number [111-42-2] Ether Diethanolamine is contained in many products, as a metalworking fluid. Traces may exist in other Ether, bis[2-(2,3-Epoxypropoxy)Ethyl] ethanolamine-containing fluids. CAS Registry Number [4206-61-5] Dictionary of Contact Allergens: Chemical Structures, Sources, and References 83

Diethyleneglycol diglycidyl ether was 156 Diethyl Phthalate contained in a reactive diethyleneglycol-based diluent of epoxy resins and caused contact derma- 58.330.1 CAS Registry Number [84-66-2] titis in three workers at a ski factory. This plasticizer increases the flexibility of plas- tics. It is also contained in deodorant formula- O tions, perfumes, emollients, and insect repellents. O O O O It can cross-react with dimethyl phthalate.

O 154.1 Suggested Reading O Jolanki R, Tarvainen K, Tatar T et al (1996) Occu- pational dermatoses from exposure to epoxy O resin compounds in a ski factory. Contact Der- matitis 34:390–396 O

155 Diethylenetriamine 156.1 Suggested Reading

CAS Registry Number [111-40-0] Capon F, Cambie MP, Clinard F et al (1996) Diethylenetriamine is a hardener in epoxy Occupational contact dermatitis caused by resins of the bisphenol A type. It has been reported computer mice. Contact Dermatitis 35:57–58 to be a sensitizer when used in an ultrasonic bath for cleaning jewels, in synthetic lubricants, or in carbonless copy paper. 157 Diethylthiourea

H Diethylthiocarbamide CAS Registry Number [105-55-5] N Diethylthiourea, a thiourea derivative, is used H N NH 2 2 mainly as a rubber chemical, particularly in solid neoprene products. 155.1 Suggested Reading S Holness DL, Nethercott JR (1993) The perfor- mance of specialized collections of bisphenol N N

A epoxy resin system components in the eval- HH uation of workers in an occupational health clinic population. Contact Dermatitis 28:216–219 157.1 Suggested Reading Jolanki R, Kanerva L, Estlander T et al (1990) Occupational dermatoses from epoxy resin Kanerva L, Estlander T, Jolanki R (1994) Occu- – compounds. Contact Dermatitis 23:172 183 pational allergic contact dermatitis caused by Kanerva L, Estlander T, Jolanki R (1990) Occu- thiourea compounds. Contact Dermatitis pational allergic contact dermatitis due to 31:242–248 diethylenetriamine (DETA) from carbonless Liippo J, Ackermann L, Lammintausta K (2011) copy paper and from an epoxy compound. Occupational allergic contact dermatitis – Contact Dermatitis 23:272 273 caused by diethylthiourea in a neoprene handle 84 J.-P. Lepoittevin and C. J. Le Coz

of a cleaning trolley. Contact Dermatitis 64:359–360

N C N 158 N-N0-Diglycidylaniline (DGA)

Phenyldiglycidylamine, N,N-Bisglycidylaniline, N,N-Diglycidylbenzenamine, bis(Epoxypropyl) 159.1 Suggested Reading phenylamine, bis(2,3-Epoxypropyl)aniline CAS Registry Number [2095-06-9] Poesen N, de Moor A, Busschots A et al (1995) N-N0-Diglycidylaniline (DGA) is an epoxy Contact allergy to dicyclohexyl carbodiimide component of glues used in the aircraft industry. and diisopropyl carbodiimide. Contact Derma- Such resin systems are present in pre-impregnated titis 32:368–369 composite materials (prepregs). It can be used in association with tetraglycidyl-4-40-methyle- nedianiline (TGMDA) and triglycidyl-p- 160 Diisopropylbenzothiazyl-2- aminophenol (TGPAP). Sulfenamide

CAS Registry Number [95-29-4] This chemical is a mercaptobenzothiazole- sulfenamide used in rubber vulcanization.

N S S 158.1 Suggested Reading N

Jappe U, Geier J, Hausen BM (2005) Contact vitiligo following a strong patch test reaction to triglycidyl-p-aminophenol in an aircraft industry worker: case report and review of the 160.1 Suggested Reading literature. Contact Dermatitis 53:89–92 Pesonen M, Suuronen K, Jolanki R et al (2015) Le Coz CJ (2004) Fiche d’éviction en cas Occupational contact dermatitis caused by ani- d’hypersensibilité au mercaptobenzothiazole line epoxy resins in the air craft industry. Con- et au mercapto mix. Ann Dermatol Venereol tact Dermatitis 73:113–118 131:846–848

159 Diisopropyl Carbodiimide 161 2,5-Dimercapto-1,3,4- Thiadiazole N,N-Methanetetraylbis-2-propanamine CAS Registry Number [693-13-0] DMTD It is used in peptide chemistry as a coupling CAS Registry Number [1072-71-5] reagent. It is very toxic and causes contact derma- This low-molecular-weight aromatic com- titis in laboratory workers. pound is used in the production of copper corro- sion inhibitors for engine oils, flame retardants, and photographic development chemicals. Seven Dictionary of Contact Allergens: Chemical Structures, Sources, and References 85 cases of industrial allergic sensitization were O H reported in a manufacturing plant. O P N S NN O O SH HS S 163.1 Suggested Reading 161.1 Suggested Reading De Moor A, Dooms-Goossens A (1996) Contact O’Driscoll JO, Beck M, Taylor S (1990) Occupa- dermatitis caused by the insecticides tional contact allergy to 2,5-dimercapto-1,3,4- and dimethoate. Contact Dermatitis – thiadiazole. Contact Dermatitis 23:268–269 35:54 55

162 Dimethoate 164 2,6-Dimethoxy-1,4- Benzoquinone CAS Registry Number [60-51-5] This organophosphorus compound is used as a CAS Registry Number [530-55-2] contact and systemic insecticide and acaricide. It 2,6-Dimethoxy-1,4-benzoquinone is an aller- induced an erythema-multiform-like contact der- gen in more than 50 different plants and wood matitis in a warehouseman in an agricultural species, e.g., mahogany, macore, sipo, wenge, consortium. oak, beech, elms, and poplar. With acamelin, it is one of the allergens of Acacia melanoxylon. Sen- sitization can occur in woodworkers such as car- S H penters, joiners, and sawyers. O P N S O O O O O

162.1 Suggested Reading

Haenen C, de Moor A, Dooms-Goossens A O (1996) Contact dermatitis caused by the insec- ticides omethoate and dimethoate. Contact Dermatitis 35:54–55 164.1 Suggested Reading Schena D, Barba A (1992) Erythema-multiforme- like contact dermatitis from dimethoate. Con- Correia O, Barros MA, Mesquita-Guimaraes J tact Dermatitis 27:116–117 (1992) Airborne contact dermatitis from the woods Acacia melanoxylon and Entandrophragma cylindricum. Contact Der- 163 Dimethoxon matitis 27:343–344 Lamminpää A, Estlander T, Jolanki R et al (1996) Omethoate Occupational allergic contact dermatitis CAS Registry Number [1113-02-6] caused by decorative plants. Contact Dermati- Contact dermatitis from omethoate- tis 34:330–335 dimethoxon is rare. 86 J.-P. Lepoittevin and C. J. Le Coz

165 (R)-3,4-Dimethoxy-Dalbergione 166.1 Suggested Reading

CAS Registry Number [37555-64-4] Gallo R, Guarrera M, Hausen BM (1996) Air- This quinone is the main allergen of borne contact dermatitis from East Indian rose- Machaerium scleroxylum Tul. (Santos rosewood, wood (Dalbergia latifolia Roxb.). Contact Pau ferro, Caviuna vermelha, Santos Dermatitis 35:60–61 palissander). Occupational sensitization mainly concerns woodworkers. 167 5,8-Dimethoxypsoralen

O Isopimpinellin O CAS Registry Number [482-27-9] Psoralens are natural photoactivatable com- pounds in plants and can cause phototoxic contact O dermatitis. For example, Cachrys libanotis L., Apiaceae-Umbelliferae family, contains 5,8- O dimethoxypsoralen.

165.1 Suggested Reading O

Chieregato C, Vincenzi C, Guerra L et al (1993) Occupational airborne contact dermatitis from Machaerium scleroxylum (Santos rosewood). O O O Contact Dermatitis 29:164–165 Lamminpää A, Estlander T, Jolanki R et al (1996) O Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- 167.1 Suggested Reading tis 34:330–335 Ena P, Cerri R, Dessi G et al (1991) Phototoxicity due to Cachrys libanotis. Contact Dermatitis 0 166 (S)-4,4 -Dimethoxy Dalbergione 24:1–5

CAS Registry Number [4646-87-1] It is an allergen of Dalbergia nigra, also 168 Dimethyl Phthalate contained in Dalbergia latifolia Roxb. (East Indian rosewood, palissander). Occupational der- CAS Registry Number [131-11-3] matitis can occur in timber workers such as car- Phthalates are plasticizers and increase the penters, sawyers, joiners, or knifegrinders. flexibility of plastics. They are also found in deodorant formulations, perfumes, emollients,

O and insect repellents.

O

O O O O O

O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 87

168.1 Suggested Reading Patch test has to be carefully interpreted, since the 1% aqueous solution has pH > 11 (personal Capon F, Cambie MP, Clinard F et al (1996) observation). Occupational contact dermatitis caused by computer mice. Contact Dermatitis 35:57–58 N NH2

169 4-N,N-(Dimethylamino) Benzenediazonium Chloride 170.1 Suggested Reading p-Diazodimethylaniline Zinc Chloride Double Angelini G, Foti C, Rigano L et al (1995) Salt 3-Dimethylaminopropylamine: a key sub- CAS Registry Number [100-04-9] stance in contact allergy to It is a diazo compound found in diazo copy cocamidopropylbetaine? Contact Dermatitis paper. It is allergenic only when unexposed. 32:96–99 Kanerva L, Estlander T, Jolanki R (1996) Occu- pational allergic contact dermatitis from N 3-dimethylaminopropylamine in shampoos. Contact Dermatitis 35:122–123 CI / ZnCl2.2 H2O Speight EL, Beck MH, Lawrence CM (1993) N Occupational allergic contact dermatitis due N to 3-dimethylaminopropylamine. Contact Der- matitis 28:49–50 169.1 Suggested Reading 171 Dimethyldiphenylthiuram Geier J, Fuchs T (1993) Contact allergy due to Disulfide 4-N,N-dimethylaminobenzene diazonium chloride and thiourea in diazo copy paper. CAS Registry Number [53880-86-7] Contact Dermatitis 28:304–305 This thiuram compound is used as an acceler- ator for rubber vulcanization. 170 3-Dimethylaminopropylamine S CAS Registry Number [109-55-7] Dimethylaminopropylamine is an aliphatic N S S N amine present in amphoteric surfactants such as liquid soaps and shampoos. It is present as a S residual impurity thought to be responsible for allergy from cocamidopropyl betaine. It is struc- turally similar to diethylaminopropylamine. It is 171.1 Suggested Reading also used as a curing agent for epoxy resins, and an organic intermediate in chemical synthesizes Le Coz CJ (2004) Fiche d’éviction en cas (ion exchangers, additives for flocculants, cos- d’hypersensibilité au thiuram mix. Ann metics and fuel additives, dyes, and pesticides). Dermatol Venereol 131:1012–1014 88 J.-P. Lepoittevin and C. J. Le Coz

172 Dimethylformamide O

CAS Registry Number [68-12-2] OMe This is an organic solvent for vinyl resins and MeO acetylene, butadiene, and acid gases. It caused O contact dermatitis in a technician at an epoxy resin factory and can provoke alcohol-induced fl ushing in exposed subjects. 173.1 Suggested Reading

O Foti C, Zambonin CG, Cassano N et al (2009) Occupational allergic contact dermatitis asso- H N ciated with dimethyl fumarate in clothing. Contact Dermatitis 61:122–124 Rantanen T (2008) The cause of the Chinese sofa/ chair dermatitis epidemic is likely to be contact 172.1 Suggested Reading allergy to dimethylfumarate, a novel potent contact sensitizer. Br J Dermatol 159:218–221 Camarasa JG (1987) Contact dermatitis from dimethylformamide. Contact Dermatitis 16:234 174 2,4-Dimethylol Phenol Cox NH, Mustchin CP (1991) Prolonged sponta- neous and alcohol-induced flushing due to the CAS Registry Number [2937-60-2] solvent dimethyl formamide. Contact Derma- 2,4-Dimethylol phenol in a compound of titis 24:69–70 resins based on phenol and formaldehyde. Cross-reactivity is possible with other phenol- derivative molecules. 173 Dimethyl Fumarate OH OH CAS Registry Number [624-49-7] Dimethyl fumarate, a strong irritant, is used as an industrial wide-spectrum biocide in Asia and mainly in China, for textiles, leather, seeds, food, and cosmetic ingredients. It provoked a world- wide epidemic of severe contact dermatitis, ini- tially from Chinese sofas sold in Finland, Great OH Britain, and France. It also induced severe burning and contact allergy due to shoes and to contami- nated clothing as well. This chemical, presents as 174.1 Suggested Reading is (white powder) or as tablets contained in little bags disposed in/or around the materials to pro- Bruze M, Zimerson E (1985) Contact allergy to tect, progressively evaporates and contaminates 3-methylol phenol, 2,4-dimethylol phenol and the environment. It is forbidden in the European 2,6-dimethylol phenol. Acta Derm Venereol Union since 2008. (Stockh) 65:548–551 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 89

Bruze M, Zimerson E (1997) Cross-reaction pat- terns in patients with contact allergy to simple methylol phenols. Contact Dermatitis 37:82–86

175 2,6-Dimethylol Phenol 176.1 Suggested Reading CAS Registry Number [2937-59-9] This substance is contained in resins based on Hansson C, Pontén A, Svedman C et al (2014) phenol and formaldehyde. Cross-reactivity is pos- Reaction profile in patch testing with allergens sible with other phenol-derivative molecules. formed during vulcanization of rubber. Contact Dermatitis 70:300–308 OH OH OH 177 Dimethylthiourea

Dimethylthiocarbamide CAS Registry Number [534-13-4] Dimethylthiocarbamide, an antioxygen agent, 175.1 Suggested Reading is responsible for sensitization, when unexposed to light from diazo papers. Bruze M, Zimerson E (1985) Contact allergy to 3-methylol phenol, 2,4-dimethylol phenol and S 2,6-dimethylol phenol. Acta Derm Venereol H H (Stockh) 65:548–551 N N Bruze M, Zimerson E (1997) Cross-reaction pat- terns in patients with contact allergy to simple methylol phenols. Contact Dermatitis 37:82–86 177.1 Suggested Reading

Geier J, Fuchs T (1993) Contact allergy due to 176 Dimethylthiocarbamyl 4-N,N-dimethylaminobenzene diazonium Benzothiazole Sulfide chloride and thiourea in diazo copy paper. Contact Dermatitis 28:304–305 DMTBS Kanerva L, Estlander T, Jolanki R (1994) Occu- CAS Registry Number [3432-25-5] pational allergic contact dermatitis caused by Dimethylthiocarbamyl benzothiazole sulfide is thiourea compounds. Contact Dermatitis formed by decomposition of the corresponding 31:242–248 disulfide and reaction with tetramethylthiuram disulfide during the vulcanization process. It has been shown that thiuram monosulfides showed 178 Dinitrochlorobenzene stronger test reaction than the corresponding thiuram disulfides and are therefore better markers DNCB, 2,4-Dinitrochlorobenzene, 2,4-Dinitro-1- of thiuram sensitivity. DMTBS appeared to be the chlorobenzene, 4-Chloro-1,3-dinitrobenzene, best marker of rubber allergy to substances of any 6-Chloro-1,3-dinitrobenzene of the thiurams, dithiocarbamates, and mercapto- benzothiazole group. 90 J.-P. Lepoittevin and C. J. Le Coz

CAS Registry Number [97-00-7] 179.1 Suggested Reading This substance is one of the strongest primary skin irritants known and a universal contact aller- Perez A, Narayan S, Sansom J (2004) Occupa- gen. Occupational dermatitis has been reported, tional contact dermatitis from but current use is decreasing or performed with 2,4-dinitrofluorobenzene. Contact Dermatitis completely closed systems. DNCB is sometimes 51:314 used for topical treatment of alopecia areata, severe warts, and cutaneous metastasis of malig- nant melanoma. 180 2,4-Dinitrotoluene

CI CAS Registry Number [121-14-12] Dinitrotoluene induced sensitization in a NO 2 worker for an explosives manufacturer, also sen- sitized to nitroglycerin.

NO 2 NO2

178.1 Suggested Reading

Adams RM, Zimmerman MC, Bartlett JB, Pres- NO2 ton JF (1971) 1-Chloro-2,4-dinitrobenzene as an algicide. Report of four cases of contact dermatitis. Arch Dermatol 103:191–193 180.1 Suggested Reading

Kanerva L, Laine R, Jolanki R et al (1991) Occu- 179 Dinitrofluorobenzene pational allergic contact dermatitis caused by nitroglycerin. Contact Dermatitis 24:356–362 DNFB, FDNB, 2,4-Dinitro-1-fluorobenzene, Sangertro-1-ntac CAS Registry Number [70-34-8] 181 Dipentamethylenethiuram DNFB is a strong skin irritant and a universal Disulfide contact allergen. It is used as an intermediate in the synthesis of pesticides and pharmaceuticals such as CAS Registry Number [94-37-1] “ ” flurbiprofen, a chemical reagent, and as a topical A rubber chemical contained in thiuram mix. sensitizer for the treatment of alopecia areata. The most frequent occupational categories are the metal industry, homemakers, health services and F laboratories, and the building industry.

NO2 S

S N N S

NO2 S Dictionary of Contact Allergens: Chemical Structures, Sources, and References 91

181.1 Suggested Reading S

Condé-Salazar L, Del-Rio E, Guimaraens D et al N S S (1993) Type IV allergy to rubber additives: a S S N 10-year study of 686 cases. J Am Acad S Dermatol 29:176–180 Condé-Salazar L, Guimaraens D, Villegas C et al (1995) Occupational allergic contact dermatitis in construction workers. Contact Dermatitis 183.1 Suggested Reading 35:226–230 ’ Kiec-Swierczynska M (1995) Occupational sen- Le Coz CJ (2004) Fiche d éviction en cas ’ sitivity to rubber. Contact Dermatitis d hypersensibilité au thiuram mix. Ann – 32:171–172 Dermatol Venereol 131:1012 1014 Pföhler C, Körner R, Müller CS et al (2011) Occupational allergic contact dermatitis of the ears caused by thiurams in a headset. Contact 184 Dipentene Dermatitis 65:242–243 CAS Registry Number [138-86-3] Dipentene corresponds to a racemic mixture of 182 Dipentamethylenethiuram d-limonene and l-limonene. Dipentene can be Hexasulfide prepared from wood turpentine or by synthesis. It is used as a solvent for waxes, rosin and gums, CAS Registry Number [971-15-3] in printing inks, perfumes, rubber compounds, This thiuram compound is used as an acceler- paints, enamels, and lacquers. An irritant and sen- ator for rubber vulcanization. sitizer, dipentene caused contact dermatitis mainly in painters, polishers, and varnishers.

S

S S S N N S S S

S

182.1 Suggested Reading

Le Coz CJ (2004) Fiche d’éviction en cas d’hypersensibilité au thiuram mix. Ann 184.1 Suggested Reading Dermatol Venereol 131:1012–1014 Martins C, Gonçalo M, Gonçalo S (1995) Allergic contact dermatitis from dipentene in wax pol- 183 Dipentamethylenethiuram ish. Contact Dermatitis 33:126–127 Tetrasulfide Moura C, Dias M, Vale T (1994) Contact derma- titis in painters, polishers and varnishers. Con- CAS Registry Number [120-54-7] tact Dermatitis 31:51–53 Dipentamethylenethiuram tetrasulfide is a Pesonen M, Suomela S, Kuuliala O et al (2014) thiuram compound used as an accelerator for rub- Occupational contact dermatitis caused by d- ber vulcanization. limonene. Contact Dermatitis 71:273–279 92 J.-P. Lepoittevin and C. J. Le Coz

185 Diphencyprone 186.1 Suggested Reading

2,3-Diphenylcyclopropenone Fernández-Jorge B, Goday Buján J, Fernández- CAS Registry Number [886-38-4] Torres R et al (2008) Concomitant allergic Diphencyprone is a potent contact allergen contact dermatitis from diphenhydramine and used in topical immunotherapy to treat some metronidazole. Contact Dermatitis 59:115–116 severe alopecia areata. It is responsible for occu- Rodríguez-Jiménez B, Domínguez-Ortega J, pational contact dermatitis in chemists and derma- González-García JM et al (2009) tology department staff. Dimenhydrinate-induced fixed drug eruption in a patient who tolerated other antihistamines O J Investig Allergol Clin Immunol 19:334–335 Yamada S, Tanaka M, Kawahara Y et al (1998) Photoallergic contact dermatitis due to diphen- hydramine hydrochloride. Contact Dermatitis 38:282

187 N,N0-Diphenyl-4- 185.1 Suggested Reading Phenylenediamine Sansom JE, Molloy KC, Lovell CR (1995) Occu- DPPD pational sensitization to diphencyprone in a CAS Registry Number [74-31-7] chemist. Contact Dermatitis 32:363 A rubber accelerant, formerly contained in Temesvári E, González R, Marschalkó M et al (2004) “black-rubber mix.” The most frequent occupa- Age dependence of diphenylcyclopropenone tional categories are in the metal industry, home- sensitization in patients with alopecia areata. Con- makers, health services and laboratories, and the tact Dermatitis 50:381–382 building industry.

186 Diphenhydramine (Hydrochloride) H N CAS Registry Number [58-73-1] (CAS Registry Number [147-24-0]) This antihistaminic drug with sedative proper- ties is mainly sold over the counter. It can be used both topically (treatment of pruritus) and orally for its antiallergic, antiemetic, sedative, and anticough N properties. Allergic or photoallergic contact derma- H titis and fixed drug eruption seem to be rare.

N O 187.1 Suggested Reading

HCl Condé-Salazar L, Del-Rio E, Guimaraens D et al (1993) Type IV allergy to rubber additives: a 10-year study of 686 cases. J Am Acad Dermatol 29:176–180 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 93

0 Kiec-Swierczynska M (1995) Occupational sen- 189 4,4 -Diphenylmethane sitivity to rubber. Contact Dermatitis Diisocyanate 32:171–172 Von Hintzenstern J, Heese A, Koch HU et al MDI (1991) Frequency, spectrum and occupational CAS Registry Number [101-68-8] relevance of type IV allergies to rubber MDI is used in the manufacture of various chemicals. Contact Dermatitis 24:244–252 polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, binding agents, syn- thetic rubbers, and elastomeric fibers. 188 1,3-Diphenylguanidine

CAS Registry Number [102-06-7] Diphenylguanidine is a rubber sensitizer that can induce immediate-type reactions and delayed- OCN NCO type contact allergy. It was formerly contained in “carba mix.” Occupational exposure concerns fin- ished rubber items and the rubber manufacturing 189.1 Suggested Reading industry. The most frequent occupational catego- ries are metal industry, homemakers, health ser- Estlander T, Keskinen H, Jolanki R et al (1992) vices and laboratories, and the building industry. Occupational dermatitis from exposure to polyurethane chemicals. Contact Dermatitis 27:161–165 Hannu T, Estlander T, Jolanki R (2005) Allergic H contact dermatitis due to MDI and MDA from N accidental occupational exposure. Contact Dermatitis 52:108–109 H Mancuso G, Reggiani M, Berdondini RM (1996) N N Occupational dermatitis in shoemakers. Con- H tact Dermatitis 34:17–22

188.1 Suggested Reading 190 Diphenylthiourea

Bruze M, Kestrup L (1994) Occupational allergic CAS Registry Number [102-08-9] contact dermatitis from diphenylguanidine in a It is a rubber chemical used as an accelerator gas mask. Contact Dermatitis 31:125–126 and stabilizing agent in neoprene. Condé-Salazar L, Del-Rio E, Guimaraens D et al (1993) Type IV allergy to rubber additives: a 10-year study of 686 cases. J Am Acad S Dermatol 29:176–180 Kiec-Swierczynska M (1995) Occupational sen- N N sitivity to rubber. Contact Dermatitis 32:171–172 H H Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. Con- 190.1 Suggested Reading tact Dermatitis 34:17–22 Kanerva L, Estlander T, Jolanki R (1994) Occu- pational allergic contact dermatitis caused by 94 J.-P. Lepoittevin and C. J. Le Coz

thiourea compounds. Contact Dermatitis occupational relevance. Constant concomitant 31:242–248 reactions with Disperse Blue 106, and even to Kiec-Swierczynska M (1995) Occupational sen- photographic developers CD1–4, are due to their sitivity to rubber. Contact Dermatitis chemical similarities. 32:171–172 N N 191 Disperse Blue 106 O2N S N

CAS Registry Number [12223-01-7] N This clothing dye used in synthetic fibers is one O of the most potent sensitizers in clothes. Allergic contact dermatitis is relatively frequent in con- O sumers. Occupational textile dye dermatitis was reported in a ready-to-wear shop. Constant con- comitant reactions with Disperse Blue 124 are due 192.1 Suggested Reading to their chemical similarities, as with photograph developers CD1, CD2, CD3, and CD4. Raccagni AA, Baldari U, Righini MG (1996) Airborne dermatitis in a painter. Contact Der- – N matitis 35:119 120 Soni BP, Sherertz EF (1996) Contact dermatitis in N the textile industry: a review of 72 patients. Am O2N S N J Contact Dermatitis 7:226–230

N Disperse Dyes OH Disperse dyes are so called because they are partially soluble in water. These synthetic dyes have either an anthraquinone (disperse anthraqui- 191.1 Suggested Reading none dyes) or an azoic structure (disperse azo dyes). They are the most commonly employed Menezes-Brandão F, Altermatt C, Pecegueiro M dyes, sometimes as hair dyes, but chiefly in the et al (1985) Contact dermatitis to Disperse textile industry to color synthetic fibers such as Blue 106. Contact Dermatitis 13:80–84 polyester, acrylic and acetate, and sometimes Mota F, Silva E, Varela P, Azenha A, Massa A nylon, particularly in stockings. They are not (2000) An outbreak of occupational textile dye used for natural fibers. These molecules are the dermatitis from Disperse Blue 106. Contact main textile sensitizers. Dermatitis 43:235–236

193 Disperse Orange 3 192 Disperse Blue 124 CI 11005 CAS Registry Number [15141-18-1] CAS Registry Number [730-40-5] This clothing dye used in synthetic fibers is one Disperse Orange 3 is an azo dye that can of the most potent sensitizers in clothes. It is a induce contact dermatitis in workers in the textile textile dye responsible for occupational contact industry. It is positive in a great majority of dermatitis in the textile industry. A positive PPD-positive people, because of hydrolysis in patch test reaction was observed in a painter sen- the skin into PPD. Disperse Orange 3 can also sitized to phthalocyanine dyes, with no be found in some semipermanent hair dyes. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 95

NH2 explained to be very frequent because of skin transformation of Disperse Orange 3 into PPD. N N 194.1 Suggested Reading

O2N Goon AT, Gilmour NJ, Basketter DA et al (2003) High frequency of simultaneous sensitivity to 193.1 Suggested Reading Disperse Orange 3 in patients with positive patch tests to para-phenylenediamine. Contact – Condé-Salazar L, Baz M, Guimaraens D et al Dermatitis 48:248 250 (1995) Contact dermatitis in hairdressers: Le Coz CJ, Jelen G, Goossens A et al (2004) patch test results in 379 hairdressers Disperse (yes), Orange (yes), 3 (no): what do (1980–1993). Am J Contact Dermatitis we test in textile dye dermatitis? Contact Der- – 6:19–23 matitis 50:126 127 Soni BP, Sherertz EF (1996) Contact dermatitis in the textile industry: a review of 72 patients. Am J Contact Dermat 7:226–230 195 Disperse Red 11

CI 62015 194 Disperse Orange 31 CAS Registry Number [2872-48-2] Disperse Red 11 is an example of disperse dye CI 111135 anthraquinone type. CAS Registry Numbers [61968-38-5] (and [68391-42-4]?) O NH2 The synthetic azo dye Disperse Orange 31 was O wrongly substituted by Disperse Orange 3 in patch test materials from chemotechnique. This situation explains why a relatively low percentage of patients positive to PPD were positive to Dis- perse Orange 3, although a co-reaction is O NH

NO2

NO2 N N N N N N N

N

O Disperse Orange 31 hydrolyzed

OH O

Disperse Orange 31 96 J.-P. Lepoittevin and C. J. Le Coz

195.1 Suggested Reading O

S CN Cronin E (1980) Contact dermatitis. Churchill Livingstone, Edinburgh, pp 36–92 S CN

O 196 Disperse Yellow 3

CI 11855 197.1 Suggested Reading CAS Registry Number [2832-40-8] This azoic dye is responsible for textile derma- Koch P (1996) Occupational allergic contact der- titis from stockings and occupational contact der- matitis and airborne contact dermatitis from matitis in workers in the textile industry. It can be 5 fungicides in a vineyard worker. Cross- found in some semipermanent hair dyes. reactions between fungicides of the dithiocar- bamate group? Contact Dermatitis 34:324–329 HO

N 198 Dodecyl Gallate O N Lauryl Gallate N CAS Registry Number [1166-52-5] This gallic acid ester (E 310) is an antioxidant H added to food and cosmetics to prevent oxidation of unsaturated fatty acids. Cases were reported in 196.1 Suggested Reading workers of the food industry, gallate being contained in margarine, and from washing powder. Condé-Salazar L, Baz M, Guimaraens D et al O (1995) Contact dermatitis in hairdressers: patch test results in 379 hairdressers HO (1980–1993). Am J Contact Dermat 6:19–23 O Soni BP, Sherertz EF (1996) Contact dermatitis in 9 the textile industry: a review of 72 patients. Am HO J Contact Dermat 7:226–230 OH

197 Dithianone 198.1 Suggested Reading CAS Registry Number [3347-22-6] Dithianone is an anthraquinone derivative, De Groot AC, Gerkens F (1990) Occupational used as a fungicide agent. With cymoxanil, it is airborne contact dermatitis from octyl gallate. contained in Aktuan®. Cases in agricultural Contact Dermatitis 23:184–186 workers were reported sparsely. Mancuso G, Staffa M, Errani A et al (1990) Occu- pational dermatitis in animal feed mill workers. Contact Dermatitis 22:37–41 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 97

199 Doxepin 200.1 Suggested Reading

CAS Registry Number [1668-19-5] Hald M, Bergendorf O, Isaksson M et al (2018) This benzoxepin tricylcic drug has antidepres- Allergic contact dermatitis caused by plastic items sant, , antiitching, and antihista- containing the ultraviolet absorber drometrizole. mine properties. After oral use, it has been Contact Dermatitis 79:110–112 developed as a topical antiitching agent. Allergic contact dermatitis is not infrequent. 201 Epichlorhydrin

N 1-Chloro-2,3-epoxypropane CAS Registry Number [106-89-8] Epoxy resin of the bisphenol A type is synthe- sized from epichlorhydrin and bisphenol A. It leads to bisphenol A diglycidyl ether, which is O the monomer of bisphenol A-based epoxy resins. Sensitization to epichlorhydrin occurs mainly in workers of the epoxy resin industry. Sensitization 199.1 Suggested Reading in individuals not working at epoxy resin plants is rare. It has, however, been described to occur Buckley DA (2000) Contact allergy to doxepin. following exposure to a soil fumigant, due to Contact Dermatitis 43:231–232 solvent cement, and in a worker in a pharmaceu- Taylor JS, Praditsuwan P, Handel D, Kuffner G tical plant, in a division of drug synthesis. (1996) Allergic contact dermatitis from Epichlorhydrin was used for the production of doxepin cream. One-year patch test clinic drugs propranolol and oxprenolol. experience. Arch Dermatol 132:515–518 Wakelin SH, Rycroft RJG (2007) Allergic contact O dermatitis from doxepin. Contact Dermatitis CI 40:214

200 Drometrizole 201.1 Suggested Reading

CAS Registry Number [2440-22-4] Holness DL, Nethercott JR (1993) The perfor- Drometrizole is an ultraviolet (UV) light mance of specialized collections of bisphenol absorber and stabilizer used in plastic and rubber A epoxy resin system components in the eval- fi products, dyes, synthetic and natural bers, uation of workers in an occupational health waxes, and detergents. It can also be used as an clinic population. Contact Dermatitis ingredient in cosmetics. 28:216–219 Rebandel P, Rudzki E (1990) Dermatitis caused by epichlorhydrin, oxprenolol hydrochloride and propranolol hydrochloride. Contact Der- matitis 23:199 Van Jost T, Roesyanto ID, Satyawan I (1990) Occupational sensitization to epichlorhydrin (ECH) and bisphenol-A during the manufacture of epoxy resin. Contact Dermatitis 22:125–126 98 J.-P. Lepoittevin and C. J. Le Coz

202 Epoxy Resins of the Bisphenol 203 (2,3-Epoxypropyl) A Type trimethylammonium Chloride

These resins are synthesized from bisphenol A and EPTMAC, Glycidyl Trimethyl Ammonium Chlo- epichlorhydrin. Hardeners are added, such as ride, Oxiranemethanaminium, N,N,N-Trimethyl amines (ethylenediamine, diethylenetriamine, Chloride triethylenetetramine, isophoronediamine, triethy- CAS Registry Number [3033-77-0] lenetriamine, and 4,4-diaminophenylmethane) or Used in the production of cationic starch for acid anhydrides (phthalic anhydride). Reactive dil- the paper industry; EPTMAC caused contact der- uents may be added, such as allyl glycidyl ether, matitis in workers. butanediol diglycidyl ether, n-butyl glycidyl ether, o-cresyl glycidyl ether, hexanediol diglycidyl ether, O neopentyl glycol diglycidyl ether, phenyl glycidyl ether, glycidyl ester of synthetic fatty acids, and + glycidyl ether of aliphatic alcohols (Epoxide 8). N − C1

O O O O O O

OH n

202.1 Suggested Reading 203.1 Suggested Reading

Holness DL, Nethercott JR (1993) The perfor- Estlander T, Jolanki R, Kanerva L (1997) Occu- mance of specialized collections of bisphenol pational allergic contact dermatitis from A epoxy resin system components in the evalu- 2,3-epoxypropyl trimethyl ammonium chlo- ation of workers in an occupational health clinic ride (EPTMAC) and Kathon R LX in a starch population. Contact Dermatitis 28:216–219 modification factory. Contact Dermatitis Aalto-Korte K, Pesonen M, Suuronen K (2015) 36:191–194 Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sen- sitizing products and diagnosis. Contact Der- matitis 73:336–342 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 99

204 Estradiol 205.1 Suggested Reading

17-β-Estradiol, (17β)-Estra-1,3,5(10)-triene-3,17- Mancuso G, Staffa M, Errani A et al (1990) Occu- diol pational dermatitis in animal feed mill workers. CAS Registry Number [50-28-2] Contact Dermatitis 22:37–41 Natural estradiol, used in transdermal systems for hormonal substitution, can induce allergic contact dermatitis, with the risk of systemic con- 206 Ethyl Alcohol tact dermatitis after oral reintroduction. Ethanol OH CAS Registry Number [64-17-5] Ethanol is widely used for its solvent and anti- septic properties. It is rather an irritant, and sensi- H tization has rarely been reported.

H H OH

HO 206.1 Suggested Reading 204.1 Suggested Reading Okazawa H, Aihara M, Nagatani et al (1998) Gonçalo M, Oliveira HS, Monteiro C et al (1999) Allergic contact dermatitis due to ethyl alco- Allergic and systemic contact dermatitis from hol. Contact Dermatitis 38:233 estradiol. Contact Dermatitis 40:58–59 Ophaswongse S, Maibach HI (1994) Alcohol der- matitis: allergic contact dermatitis and contact urticaria syndrome. Contact Dermatitis 30:1–6 205 Ethoxyquin Patruno C, Suppa F, Sarraco G et al (1994) Aller- gic contact dermatitis due to ethyl alcohol. 1,2-Dihydro 6-ethoxy 2,2,4-trimethylquinolein, Contact Dermatitis 31:124 Santoquin®, Santoflex® CAS Registry Number [91-53-2] Ethoxyquin is used as an antioxidant in animal 207 4-Ethylpyridine feed and caused contact dermatitis in a worker at an animal feed mill. CAS Registry Number [536-75-4] 4-Ethylpyridine is used as a monomer in poly- H mer chemistry. N

O CH3

N 100 J.-P. Lepoittevin and C. J. Le Coz

207.1 Suggested Reading contact dermatitis. In delayed contact allergy, it seems that cross-reaction can be observed to Sasseville D, Balbul A, Kwong P, Yu K (1996) epichlorhydrin or epoxypropane. Contact sensitization to pyridine derivatives. Contact Dermatitis 35:101–102 O

208 Ethylbutylthiourea 209.1 Suggested Reading

CAS Registry Number [32900-06-4] Birnie AJ, English JS (2006) Ethylene oxide Ethylbutylthiourea is an accelerator used with allergy may have been confirmed by patch other thiourea derivatives in the production of testing to a similar epoxy compound. Contact neoprene rubber. It is also contained in glues, Dermatitis 55:126 mainly neoprene type. Kerre S, Goossens A (2009) Allergic contact der- matitis to ethylene oxide. Contact Dermatitis S 61:47–48 Lerman Y, Ribak J, Skulsky M et al (1995) An outbreak of irritant contact dermatitis from eth- N N ylene oxide among pharmaceutical workers. H H Contact Dermatitis 33:280–281

208.1 Suggested Reading 210 Ethylenediamine

Bergendorff O, Persson CML, Hansson C (2004) CAS Registry Number [107-15-3] HPLC analysis of alkyl thioureas in an ortho- Ethylenediamine is used in numerous indus- paedic brace and patch testing with pure trial processes as a solvent for casein or albumin, ethylbutylthiourea. Contact Dermatitis as a stabilizer in rubber latex, and as a textile 51:273–277 lubricant. It can be found in epoxy resin hard- Kanerva L, Estlander T, Jolanki R (1994) Occu- eners, cooling oils, fungicides, and waxes. Con- pational allergic contact dermatitis caused by tact dermatitis from ethylenediamine is almost thiourea compounds. Contact Dermatitis exclusively due to topical medicaments. Occu- 31:242–248 pational contact dermatitis in epoxy resin Roberts JL, Hanifin JM (1980) Contact allergy systems is rather infrequent. Ethylenediamine and cross-reactivity to substituted thiourea can cross-react with triethylenetetramine and compounds. Contact Dermatitis 6:138–139 diethylenetriamine. Ethylenediamine was found to be responsible for sensitization in pharmacists handling aminophylline suppositories, in nurses 209 Ethylene Oxide preparing and administering injectable theophyl- line, and in a laboratory technician in the manu- CAS Registry Number [75-21-8] facture of aminophylline tablets. Ethylene oxide is a very strong irritant widely used in the chemical industry and as a sterilizer of NH2 medical supplies, pharmaceutical products, and H2N food. It can produce immediate (urticaria, asthma, anaphylaxis) or delayed reactions (irritant rather than allergic contact dermatitis). For example, residues in masks or dressings can produce irritant Dictionary of Contact Allergens: Chemical Structures, Sources, and References 101

210.1 Suggested Reading 212 Ethylhexylglycerin

Chieregato C, Vincenzi C, Guerra L et al (1994) Octoxyglycerin Occupational allergic contact dermatitis due to CAS Registry Number [70445-33-9] ethylenediamine dihydrochloride and cresyl This glycerol monoalkylether is used as a skin glycidyl ether in epoxy resin systems. Contact conditioning agent, with bactericidal properties Dermatitis 30:120 against Gram-positive bacteria. Corazza M, Mantovani L, Trimurti L et al (1994) Occupational contact sensitization to OH ethylenediamine in a nurse. Contact Dermatitis 31:328–329 O OH Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. Con- – tact Dermatitis 34:17 22 212.1 Suggested Reading Sasseville D, Al-Khenaizan S (1997) Occupa- tional contact dermatitis from ethylenediamine Aerts O, Verhulst L, Goossens A (2016) in a wire-drawing lubricant. Contact Dermati- Ethylhexylglycerin: a low-risk, but highly rel- tis 3:228–229 evant, sensitizer in “hypo-allergenic” cos- metics. Contact Dermatitis 74:281–288 Linsen G, Goossens A (2002) Allergic contact 211 Ethylenethiourea dermatitis from ethylhexylglycerin. Contact Dermatitis 47:169 CAS Registry Number [96-45-7] Ethylenethiourea, a thiourea derivative, is a rubber chemical. It caused contact dermatitis 213 Eugenol mainly in rubber workers. CAS Registry Number [97-53-0] H Eugenol is a fragrance allergen obtained from N many natural sources. Occupational sensitization to eugenol may occur in dental profession S workers. Eugenol is contained in “fragrance N mix” and has to be listed by name in cosmetics H within the EU.

OH 211.1 Suggested Reading O

Bruze M, Fregert S (1983) Allergic contact der- matitis from ethylenethiourea. Contact Derma- titis 9:208–212 Kanerva L, Estlander T, Jolanki R (1994) Occu- pational allergic contact dermatitis caused by thiourea compounds. Contact Dermatitis 31:242–248 102 J.-P. Lepoittevin and C. J. Le Coz

NH 213.1 Suggested Reading 2 O O NH2 S N H2N Rudzki E, Rebandel P, Grzywa Z (1989) Patch S N NH2 tests with occupational contactants in nurses, N doctors and dentists. Contact Dermatitis S 20:247–250 Sanchez-Pérez J, Garcia-Diez A (1999) Occupa- 215.1 Suggested Reading tional allergic contact dermatitis from eugenol, oil of cinnamon and oil of cloves in a physio- Guimaraens D, Gonzales MA, Condé-Salazar L therapist. Contact Dermatitis 41:295–296 (1994) Occupational allergic contact dermatitis from intermediate products in famotidine syn- ® thesis. Contact Dermatitis 31:259–260 214 Euxyl K 400 (See 1,2-Dibromo- Monteseirin J, Conde J (1990) Contact eczema 2,4-Dicyanobutane from famotidine. Contact Dermatitis 22:290 and Phenoxyethanol)

® Euxyl K 400 is a mixture of 1,2-dibromo-2,4- 216 Farnesol dicyanobutane 20% and phenoxyethanol 80%, widely utilized as a preservative in cosmetics, 3,7,11-Trimethyldodeca-2,6,10-trienol (Four hand creams, and toiletries but also in water- Isomers) based paints, glues, metalworking fluids, and CAS Registry Numbers [4602-84-0] for the detergents. Sensitization was reported in mas- mixture, [106-28-5] for the trans/trans, [3790-71- seurs, in a beautician, an offset printer, and a 4] for the cis/trans, [3879-60-5] for the trans/cis, hospital cleaner. We observed four cases of hand and [16106-95-9] for the cis/cis contact dermatitis in metalworkers, due to the Farnesol is one of the most frequent contact so-called Euxyl® K 400 contained in barrier allergens in perfumes. It is contained in small creams. No sensitization was observed to amounts in Myroxylon pereirae and poplar buds. phenoxyethanol (personal cases). It is a blend of four diastereosiomers trans/cis.As a fragrance allergen, farnesol has to be mentioned by name in cosmetics within the EU. 214.1 Suggested Reading

Aalto-Korte K, Jolanki R, Estlander T et al (1996) Occupational allergic contact dermatitis OH caused by Euxyl K 400. Contact Dermatitis 35:193–194 216.1 Suggested Reading

215 Famotidine Frosch PJ, Johansen JD, Menné T et al (2002) Further important sensitizers in patients sensi- CAS Registry Number [76824-35-6] tive to fragrances. Contact Dermatitis Contact dermatitis in a nurse from famotidine, 47:78–85 an H2-receptor agonist, was described. In indus- Krautheim A, Uter W, Frosch P et al (2010) Patch try, three cases were reported due to intermediates testing with fragrance mix II: results of the of the synthesis of 2-diamino-ethylene-amino- IVDK 2005–2008. Contact Dermatitis thiazolyl-methylenethiourea-dichloride and 4- 63:262–269 chloromethyl-2-guanidinothiazole-nitrochloride. Schnuch A, Uter W, Geier J et al (2004) Contact allergy to farnesol in 2021 consecutively patch Dictionary of Contact Allergens: Chemical Structures, Sources, and References 103

tested patients. Results of the IVDK. Contact 218.1 Suggested Reading Dermatitis 50:117–121 Bruynzeel DP, Tafelkruijer J, Wilks MF (1995) Contact dermatitis due to a new fungicide used 217 Fenvalerate in the tulip bulb industry. Contact Dermatitis 33:8–11 CAS Registry Number [51630-58-1] Van Ginkel CJW, Sabapathy NN (1995) Allergic Fenvalerate is an insecticide of the synthetic contact dermatitis from the newly introduced pyrethroid group, which induced sensitization in fungicide fluazinam. Contact Dermatitis farmers. 32:160–162

219 Flutamide O O 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl] O CN CI propanamide, Trifluoro-2-methyl-4-nitro-m-pro- pionotoluidide, 4-Nitro-3-trifluoromethylisobuty- ranilide, Niftolid 217.1 Suggested Reading CAS Registry Number [13311-84-7] Flutamide is an antiandrogenic hormonal anti- Sharma VK, Kaur S (1990) Contact sensitization neoplastic drug that can induce photosensitivity by pesticides in farmers. Contact Dermatitis and porphyria-like eruption. 23:77–80

CF3

O2N 218 Fluazinam O

Shirlan®, 3-Chloro-N-(3-chloro-5-trifluoromethyl- N 2-pyridyl)-trifluoro-2,6-dinitro-p-toluidine H CAS Registry Number [79622-59-6] Fluazinam is a pesticide with a broad spectrum of antifungal activity. It caused sensitization in 219.1 Suggested Reading employees in the tulip bulb industry and in farmers. Fluazinam induced contact dermatitis in Borroni G, Brazzelli V, Baldini F et al (1998) a worker in a plant where it was manufactured. Flutamide-induced pseudoporphyria. Br J Dermatol 138:711–712 NO H CI 2 Martín-Lázaro J, Goday Buján J, Parra Arrondo A N et al (2004) Is photopatch testing useful in the investigation of photosensitivity due to fl – N utamide? Contact Dermatitis 50:325 326

F3C NO2 CF3 CI 220 Folpet

Folpel, Phthalane, Trichloromethylthiophthalimide CAS Registry Number [133-07-3] 104 J.-P. Lepoittevin and C. J. Le Coz

Folpet is a pesticide, fungicide agent of formaldehyde-urea and melamine-formaldehyde thiophthalimide group. Occupational exposure resins, can be used in textiles and secondarily occurs mostly in agricultural workers or in florists. release free formaldehyde. Photosensitivity has been reported. Other resins, such as p-tert-butylphenol form- aldehyde resin or tosylamine formaldehyde resin, O do not release formaldehyde.

O NS

CCI3 HH O

221.1 Suggested Reading 220.1 Suggested Reading Flyvholm MA, Menné T (1992) Allergic contact Mark KA, Brancaccio RR, Soter NA et al (1999) dermatitis from formaldehyde. A case study Allergic contact and photoallergic contact der- focussing on sources of formaldehyde expo- matitis to plant and pesticide allergens. Arch sure. Contact Dermatitis 27:27–36 – Dermatol 135:67 70 Murray R (1991) Health aspects of carbonless Peluso AM, Tardio M, Adamo F et al (1991) copy paper. Contact Dermatitis 24:321–333 Multiple sensitization due to Rudzki E, Rebandel P, Grzywa Z (1989) Patch bis-dithiocarbamate and thiophthalimide pesti- tests with occupational contactants in nurses, cides. Contact Dermatitis 25:327 doctors and dentists. Contact Dermatitis 20:247–250 Scheman AJ, Katta R (1997) Photographic aller- 221 Formaldehyde gens: an update. Contact Dermatitis 37:130 Torresani C, Periti I, Beski L (1996) Contact urti- Methanal, Formalin caria syndrome from formaldehyde with mul- CAS Registry Number [50-00-0] tiple physical urticaria. Contact Dermatitis Sources and uses of formaldehyde are numer- 35:174–175 ous. Exposed people are mainly health workers, cleaners, painters, metalworkers, but also photog- raphers (color developers) and carbonless copy 222 Frullanolide paper users. Formaldehyde can induce contact urticaria. Formaldehyde may be the cause of l-(–)-Frullanolide: CAS Registry Number [27579- sensitization to formaldehyde releasers: benzylhe- 97-1] miformal, bromonitrodioxane, bromonitropro- d-(+)-Frullanolide: CAS Registry Number panediol (?), chloroallylhexaminium chloride or [40776-40-7] Quaternium-15, diazolidinylurea, dimethylol urea, Frullanolide is a sesquiterpene lactone, dimethyloldimethylhydantoin or DMDM hydantoin, contained in Frullania tamarisci Dum. (l- hexamethylenetetramine or methenamine, imidazoli- Frullanolide) and Frullania dilatata Dum. (d- dinylurea, monomethyloldimethylhydantoin, or frullanolide), a lichen that grows on lobed-leaf MDM hydantoin, N-methylolchloracetamide, trees such as oak and beech. Sensitivity causes paraformaldehyde and trihydroxyethylhexa- airborne and sometimes severe polymorphous hydrotriazine, or Grotan BK. Formaldehyde is used for the synthesis of many resins. Some of them, such as Dictionary of Contact Allergens: Chemical Structures, Sources, and References 105 erythema-like allergic contact dermatitis, mainly 223.1 Suggested Reading in foresters and in people using firewood, lumber- men, sawyers, carpenters, and merchants in rough Sánchez-Pérez J, Córdoba S, Jesús del Río M et al timber. (1999) Allergic contact dermatitis from furaltadone in eardrops. Contact Dermatitis 40:222 Vilaplana J, Grimalt F, Romaguera C (1990) Con- tact dermatitis from furaltadone in animal feed. Contact Dermatitis 22:232–233

O O O O 224 Furazolidone

3-(5-Nitrofurfurylideneamino)-2-oxazolidinone 222.1 Suggested Reading CAS Registry Number [67-45-8] Furazolidone belongs to the group of nitrofu- Ducombs G, Lepoittevin JP, Berl V et al (2003) rans. This antimicrobial (antibacterial and anti- Routine patch testing with frullanolide mix: an protozoal) agent is used in veterinary medicine European Environmental and Contact Derma- both topically and orally, particularly in animal titis Research Group multicentre study. Con- feed. Reactions are reported in workers exposed to – tact Dermatitis 48:158 161 it in animal feeds. Cross-reactions with other Quirino AP, Barros MA (1995) Occupational con- nitrofuran derivatives are rare. tact dermatitis from lichens and Frullania. Contact Dermatitis 33:68–69

Tomb RR (1992) Patch testing with frullania dur- N O ing a 10-year period: hazards and complica- H tions. Contact Dermatitis 26:220–223 O O O2N N N

223 Furaltadone O

5-Morpholinomethyl-3 (5-Nitrofurfurilidena- mine)-2-oxazolidinone 224.1 Suggested Reading CAS Registry Number [139-91-3] Burge S, Bransbury A (1994) Allergic contact H dermatitis due to furazolidone in a piglet med- ication. Contact Dermatitis 31:199–200 O O O2N N De Groot AC, Conemans MH (1990) Contact N allergy to furazolidone. Contact Dermatitis 22:202–205 O

This nitrofuran derivative can be added in 225 Geraniol animal feed or in eardrops. 3,7-Dimethyl-2,6-octadien-1-ol: CAS Registry Number [106-24-1] cis-Geraniol, Nerol: CAS Registry Number [106-25-2] 106 J.-P. Lepoittevin and C. J. Le Coz

trans-Geraniol, Citrol: CAS Registry Number Kiec-Swierczynska M, Kre cisz B (2001) Occu- [624-15-7] pational allergic contact dermatitis in hair- Geraniol is an olefinic terpene, constituting the dressers due to glutaraldehyde. Contact chief part of rose oil and oil of palmarosa. It is also Dermatitis 44:185–186 found in many other essential oils such as citro- Nethercott JR, Holness DL, Page E (1988) Occu- nella, lemongrass, or ylang-ylang (Cananga pational contact dermatitis due to glutaralde- odorata Hook.f. and Thoms.). It is contained in hyde in healthcare workers. Contact Dermatitis most fine fragrances and in “fragrance mix.” As a 18:193–196 fragrance allergen, geraniol has to be mentioned by name in cosmetics within the EU. 227 Glyceryl Thioglycolate

Glyceryl Monothioglycolate, Glycerol OH Monomercaptoacetate CAS Registry Number [30618-84-9] It is an acid permanent-wave ingredient, which induces contact dermatitis in hairdressers.

O 225.1 Suggested Reading O OH Frosch PJ, Johansen JD, Menné T et al (2002) Further important sensitizers in patients sensi- SH OH tive to fragrances. Contact Dermatitis 47:78–85 Kanerva L, Estlander T, Jolanki R (1995) Occu- 227.1 Suggested Reading pational allergic contact dermatitis caused by ylang-ylang oil. Contact Dermatitis Frosch PJ, Burrows D, Camarasa JG et al (1993) ’ 33:198–199 Allergic reactions to a hairdresser s series: results from 9 European centres. Contact Der- matitis 28:180–183 226 Glutaraldehyde Guerra L, Tosti A, Bardazzi F et al (1992) Contact dermatitis in hairdressers: the Italian experi- Glutaral, Pentanedial, Glutaric Dialdehyde ence. Gruppo Italiano Ricerca Dermatiti da CAS Registry Number [111-30-8] Contatto e Ambientali. Contact Dermatitis – Glutaraldehyde is a well-known sensitizer in 26:101 107 cleaners and health workers. It can also be found Van der Walle HB, Brunsveld VM (1994) Derma- in X-ray developers or in cosmetics. titis in hairdressers (I). The experience of the past 4 years. Contact Dermatitis 30:217–220 O O 228 Glycidyl 1-Naphthyl Ether 226.1 Suggested Reading 1-Naphthyl-glycidyl Ether CAS Registry Number [2461-42-9] Cusano F, Luciano S (1993) Contact allergy to Glycidyl ethers are used as reactive diluents for benzalkonium chloride and glutaraldehyde in a epoxy resins. Alpha-naphthyl glycidyl ether is dental nurse. Contact Dermatitis 28:127 formed by adding epichlorhydrin and NaOH to Dictionary of Contact Allergens: Chemical Structures, Sources, and References 107 alpha-naphthol. Contact dermatitis was reported 230 Grotan BK in workers of a chemical plant. Hexahydro-1,3,5-tris-(2-hydroxyethyl)triazine CAS Registry Number [4719-04-4] O O Grotan BK is a triazine derivative contained as a biocide in cutting fluids. It is a formaldehyde releaser. Dermatitis, delayed-type allergic con- junctivitis, and asthma were described.

OH 228.1 Suggested Reading

De Groot AC (1994) Occupational contact allergy N to alpha-naphthyl glycidyl ether. Contact Der- matitis 30:253–254 N N HO OH

229 3-Glycidyloxypropyltrime- 230.1 Suggested Reading thoxysilane Rasschaert V, Goossens A (2002) Conjunctivitis Gamma-Glycidoxypropyltrimethoxysilane, [(3- and bronchial asthma: symptoms of contact (Trimethoxysilyl)Propoxy)methyl]Oxirane allergy to 1,3,5-tris (2-hydroxyethyl)-hexa- CAS Registry Numbers [2530-83-8], [108727- hydrotriazine (Grotan BK). Contact Dermatitis 79-3], [120026-01-9], [138590-36-0] [163035- 47:116 07-2], [26348-10-7], [51938-40-0], [53029-18- Veronesi S, Guerra L, Valeri F et al (1987) Three 8], [65323-93-5], and [88385-40-4] cases of contact dermatitis sensitive to Grotan An impurity such as allyl glycidyl ether BK. Contact Dermatitis 17:255 seemed to be the sensitizing agent contained in 3-glycidyloxypropyltrimethoxysilane. 231 HC Blue No. 7 O CAS Registry Numbers [83732-72-3] and O Si [90817-34-8] O O O 6-Methoxy-N-2-methylpyridine-2,3-diamine dihydrochloride 6-Methoxy-2-methylamino-3-aminopyridine HCl 229.1 Suggested Reading This substance, with EINECS Nr. 280-622-9, is used in two component (oxidation) hair dyes. Dooms-Goossens A, Bruze M, Buysse L et al (1995) Contact allergy to allyl glycidyl ether NH2 present as an impurity in 2 HCl 3-glycidyloxypropyltrimethoxysilane, a fixing Me additive in silicone and polyurethane. Contact MeO N N Dermatitis 33:17–19 H 108 J.-P. Lepoittevin and C. J. Le Coz

231.1 Suggested Reading 233 Hexamethylene Diisocyanate

Anon (2006) Commission decision of 9 February 1,6-Hexamethylene Diisocyanate, HDI, HMDI 2006 amending decision 96/335/EC CAS Registry Number [822-06-0] establishing an inventory and a common This diisocyanate compound is used in the nomenclature of ingredients employed in cos- manufacture of various polyurethane products: metic products. Official Journal of the elastic and rigid foams, paints, lacquers, adhe- European Union, L97/1, 5.4.2006 (2006/257/ sives, binding agents, synthetics rubbers, and EC) elastomer fibers. Søsted H, Nielsen NH, Menné T (2009) Allergic contact dermatitis to the hair dye 6-methoxy-2- OCN methylamino-3-aminopyridine HCl (INCI HC NCO Blue no. 7) without cross-sensitivity to PPD. Contact Dermatitis 60:236–237 233.1 Suggested Reading

232 HC Yellow No. 7 Estlander T, Keskinen H, Jolanki R et al (1992) Occupational dermatitis from exposure to Hair Color Yellow No. 7 polyurethane chemicals. Contact Dermatitis – CAS Registry Number [104226-21-3] 27:161 165 HC Yellow no. 7 is a direct azo dye used in semipermanent hair dye preparation. Since this dye leads to PPD after hydrolysis, it explains the 234 Hexamidine allergic reaction in PPD-positive patients. CAS Registry Number [3811-75-4]

OH Hexamidine Diisethionate: CAS Registry Number [659-40-5] Hexamidine is an antiseptic active against Gram-positive bacteria and fungi, used as a disin- N OH fectant and a preservative in cosmetics. It induces papulovesicular and diffuse allergic contact N dermatitis. N

NH

NH H2N 2 O O H N 232.1 Suggested Reading 2 NH Sánchez-Pérez J, García del Río I, Alvares Ruiz S et al (2004) Allergic contact dermatitis from direct dyes for hair coloration in hairdressers’ 234.1 Suggested Reading clients. Contact Dermatitis 50:261–262 Dooms-Goossens A, Vandaele M, Bedert R et al (1989) Hexamidine isethionate: a sensitizer in topical pharmaceutical products and cos- metics. Contact Dermatitis 21:270 Le Coz CJ, Scrivener Y, Santinelli F et al (1998) Sensibilisation de contact au cours des ulcères Dictionary of Contact Allergens: Chemical Structures, Sources, and References 109

de jambe. Ann Dermatol Venereol 236.1 Suggested Reading 125:694–699 Revuz J, Poli F, Wechsler J et al (1984) Dermatites Frosch PJ, Johansen JD, Menné T et al (2002) de contact à l’hexamidine. Ann Dermatol Further important sensitizers in patients sensi- Venereol 111:805–810 tive to fragrances. Contact Dermatitis 47:78–85 Rastogi SC, Johansen JD, Menné T (1996) Natu- 235 Hexanediol Diglycidyl Ether ral ingredients based cosmetics. Content of selected fragrance sensitizers. Contact Derma- 1,6-Hexanediol Diglycidyl Ether titis 34:423–426 CAS Registry Number [16096-31-4] This chemical is a reactive diluent in epoxy resins. 237 Hydralazine

O CAS Registry Number [86-54-4] O Hydralazine Hydrochloride: CAS Registry O 2 O Number [304-20-1] Hydralazine is a hydrazine derivative used as an antihypertensive drug. Skin rashes have been 235.1 Suggested Reading described during treatment. Exposure occurs mainly in the pharmaceutical industry. Cross- Aalto-Korte K, Pesonen M, Suuronen K (2015) sensitivity is frequent with hydrazine, which is Occupational allergic contact dermatitis considered to be a potent sensitizer. caused by epoxy chemicals: occupations, sen-

sitizing products and diagnosis. Contact Der- H NH2 matitis 73:336–342 N Jolanki R, Kanerva L, Estlander T et al (1990) Occupational dermatoses from epoxy resin N compounds. Contact Dermatitis 23:172–183 N

236 Hexyl Cinnamic Aldehyde 237.1 Suggested Reading Hexyl Cinnamaldehyde, Alpha-Hexyl- Cinnamaldehyde, 2-(Phenylmethylene)octanal, Pereira F, Dias M, Pacheco FA (1996) Occupa- 2-Benzylideneoctanal tional contact dermatitis from propranolol, CAS Registry Number [101-86-0] hydralazine, and bendroflumethiazide. Contact Hexyl cinnamic aldehyde is a fragrance aller- Dermatitis 35:303–304 gen. Its presence has to be mentioned by name in cosmetics within the EU. 238 Hydrangenol

O CAS Registry Number [480-47-7] Hydrangenol is the allergen of hydrangea (Hydrangea macrophylla Thunb, Hydrangeaceae family). 110 J.-P. Lepoittevin and C. J. Le Coz

OH 240 Hydrocortisone

CAS Registry Number [50-23-7] Hydrocortisone is the principal hormone produced by the adrenal cortex and is O used topically or systemically. It belongs to the allergenic A group. Marker of allergy is tixocortol OH O pivalate.

O 238.1 Suggested Reading OH OH Avenel-Audran M, Hausen BM, Le Sellin J et al HO (2000) Allergic contact dermatitis from H hydrangea – is it so rare? Contact Dermatitis 43:189–191 H H Kuligowski ME, Chang A, Leemreize JHM (1992) Allergic contact hand dermatitis from O hydrangea: report of a 10th case. Contact Der- matitis 26:269–270 240.1 Suggested Reading

239 Hydrazine Le Coz CJ (2002) Fiche d’éviction en cas d’hypersensibilité au pivalate de tixocortol. CAS Registry Number [302-01-2] Ann Dermatol Venereol 129:348–349 Hydrazine sulfate CAS Registry Number Lepoittevin JP, Drieghe J, Dooms-Goossens A [10034-93-2], dihydrobromide CAS Registry (1995) Studies in patients with corticosteroid Number [23268-00-0], and hydrochloride CAS contact allergy. Understanding cross-reactivity Registry Number [14011-37-1] have been among different steroids. Arch Dermatol reported as occupational sensitizers, mainly in 131:31–37 soldering flux.

H2NNH2 241 Hydrocortisone 17-Butyrate

CAS Registry Number [13609-67-1] 239.1 Suggested Reading Hydrocortisone 17-butyrate is a C17 ester of hydrocortisone. It represents the D2 group of cor- Goh CL, Ng SK (1987) Airborne contact derma- ticosteroids, non C16 methylated with a C17 ester: titis to colophony in soldering flux. Contact hydrocortisone 17-butyrate, hydrocortisone Dermatitis 17:89–91 17-valerate, Wrangsjö K, Martensson A (1986) Hydrazine (17-propionate and 21-acetate), methylpredniso- contact dermatitis from gold plating. Contact lone aceponate, and prednicarbate. It is sometimes Dermatitis 15:244–245 hydrolyzed in vivo into hydrocortisone, giving allergic reactions to group-A-sensitized people. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 111

O 243 Hydroquinone OH O O HO 1,4-Benzenediol CAS Registry Number [123-31-9] H Hydroquinone is used in photography devel- opers (black and white, X-ray, and microfilms), in H H plastics, and in hair dyes as an antioxidant and hair colorant. Hydroquinone is found in many skin O bleaching creams.

OH 241.1 Suggested Reading

Le Coz CJ (2002) Fiche d’éviction en cas d’hypersensibilité au 17 butyrate d’hydrocortisone. Ann Dermatol Venereol OH 129:931 Lepoittevin JP, Drieghe J, Dooms-Goossens A (1995) Studies in patients with corticosteroid 243.1 Suggested Reading contact allergy. Understanding cross-reactivity among different steroids. Arch Dermatol Barrientos N, Ortiz-Frutos J, Gomez E et al (2001) – 131:31 37 Allergic contact dermatitis from a bleaching cream. Am J Contact Dermat 12:33–34 Gebhardt M, Geier J (1996) Evaluation of patch 242 Hydrogen Peroxide test results with denture material series. Con- tact Dermatitis 34:191–195 CAS Registry Number [7722-84-1] Scheman AJ, Katta R (1997) Photographic aller- Hydrogen peroxide is an oxidizing agent used gens: an update. Contact Dermatitis 37:130 as a topical antiseptic, and as part of permanent hair-dyes and color-removing preparations, and as a neutralizing agent in permanent waving. The 244 (S)-4-Hydroxy-4- concentration of the hydrogen peroxyde solution Methoxydalbergione is expressed in volume or percentage: Ten vol- umes correspond to 3%. It is an irritant. CAS Registry Number [3755-63-3] (S)-4-Hydroxy-4-methoxydalbergione is one O H of the allergens Brazilian rosewood or Palissander H O (Dalbergia nigra All., Papilionaceae family), cocobolo (Dalbergia retusa Hemsl., Dalbergia 242.1 Suggested Reading granadilla, and Dalbergia hypoleuca), or grenadil (Dalbergia melanoxylon Guill. and Perr.). Aguirre A, Zabala R, Sanz De Galdeano C et al (1994) Positive patch tests to hydrogen perox- O ide in 2 cases. Contact Dermatitis 30:113

CH3O OH O 112 J.-P. Lepoittevin and C. J. Le Coz

244.1 Suggested Reading Hydroxylammonium Sulfate – Hydroxylamine Sulfate, Oxammonium Sulfate: CAS Registry Hausen BM (1981) Wood injurious to human Number [7803-49-8] health. A manual. De Gruyter, Berlin Hydroxylamine and its salts are used in various branches of industry, as reducing agents in color film developers or as reagents in laboratories. 245 Hydroxycitronellal OH OH - + - + 7-Hydroxycitronellal, Citronellal Hydrate, Cl N H H HO NH2 SO3 N Laurine, Muguet Synthetic HH H H CAS Registry Number [107-75-5] Hydroxycitronellal is a classical fragrance allergen, found in many products. It is contained 246.1 Suggested Reading in “fragrance mix.” It has to be listed by name in the cosmetics of the EU. Aguirre A, Landa N, Gonzalez M et al (1992) Allergic contact dermatitis in a photographer. Contact Dermatitis 27:340–341 Estlander T, Jolanki T, Kanerva L (1997) O Hydroxylammonium chloride as sensitizer in OH a water laboratory. Contact Dermatitis 36:161–162 Goh CL (1990) Allergic contact dermatitis and 245.1 Suggested Reading onycholysis from hydroxylamine sulphate in colour developer. Contact Dermatitis 22:109 Corazza M, Virgili A, Bertoldi AM et al (2016) Allergic contact dermatitis caused by insect repellent wipes. Contact Dermatitis 247 Hydroxymethylpentacyclo- 74:295–296 hexenecarboxaldehyde Rastogi SC, Johansen JD, Frosch P et al (1998) ® Deodorants on the European market: quantita- Lyral , Hydroxyisohexyl 3-Cyclohexene Ca- tive chemical analysis of 21 fragrances. Con- rboxaldehyde, 4-(4-Hydroxy-4-methylpentyl)- tact Dermatitis 38:29–35 3-cyclohexene-1-carboxaldehyde, Svedman C, Bruze M, Johansen JD et al (2003) 4-(4-Hydroxy-4-methylpentyl)cyclohex-3-ene- Deodorants: an experimental provocation carbaldehyde study with hydroxycitronellal. Contact Derma- CAS Registry Number [31906-04-4] ® titis 48:217–223 Lyral is a synthetic blend of two isomers and one of the most frequently encountered allergens in perfumes. It has to be listed by name in the 246 Hydroxylamine ingredients of cosmetics in the EU, according to and Hydroxylammonium Salts the seventh amendment of the cosmetic directive 76/768/EEC. Hydroxylamine: CAS Registry Number [7803- O 49-8] OH OH Hydroxylammonium Chloride – Hydroxyl- O amine Hydrochloride, Oxammonium Hydrochlo- ride: CAS Registry Numbers [5470-11-1] Dictionary of Contact Allergens: Chemical Structures, Sources, and References 113

247.1 Suggested Reading household detergents. Hypochlorites have caused hand, diffuse, or periulcerous dermatitis, due to Braendstrup P, Johansen JD (2008) Hydroxyisohexyl bleach settings and detergents, swimming pool 3-cyclohexenecarboxaldehyde (Lyral) is still a water, endodontic treatment solution, or ulcer frequent allergen. Contact Dermatitis 59:187–188 treatment. Johansen JD, Frosch PJ, Svedman C et al (2003) Hydroxyisohexyl 3-cyclohexene carboxaldehyde − Cl O + O O Cl Na Cl Ca Cl – known as Lyral: quantitative aspects and risk HO assessment of an important fragrance allergen. Hypochlorous acid Sodium hypochloriteCalcium hypochlorit e Contact Dermatitis 48:310–316 248.1 Suggested Reading 248 Hypochlorous Acid and Hypochlorites Salphale PS, Shenoi SD (2003) Contact sensitiv- ity to calcium hypochlorite. Contact Dermatitis 48:162 Hypochlorous Acid: CAS Registry Number Sasseville D, Geoffrion CT, Lowry RN (1999) [7790-92-3] Allergic contact dermatitis from chlorinated Sodium Hypochlorite: CAS Registry Number swimming pool water. Contact Dermatitis [7681-52-9] 41:347–348 Sodium Hypochlorite Hydrate: CAS Registry Number [55248-17-4] Sodium Hypochlorite Pentahydrate: CAS Reg- 249 Imidazolidinyl Urea istry Number [10022-70-5] Sodium Hypochlorite Heptahydrate: CAS Germall® 115, IMIDUREA® Registry Number [6431-03-9] CAS Registry Number [39236-46-9] Calcium Hypochlorite: CAS Registry Number Imidazolidinyl urea, a formaldehyde releaser [7778-54-3] related to diazolidinyl urea (see above), is used as Calcium Hypochlorite Dihydroxide: CAS an antimicrobial agent very active against Gram- Registry Number [12394-14-8] positive and Gram-negative bacteria, used as a Calcium Hypochlorite Dihydrate: CAS Regis- synergist in combination with parabens. It is try Number [22464-76-2] used as a preservative in aqueous products, Calcium Sodium Hypochlorite: CAS Registry mainly in cosmetics, toiletries, and liquid soaps. Number [53053-57-9] Lithium Hypochlorite: CAS Registry Number H H H H [13840-33-0] HO OH N NNN Potassium Hypochlorite: CAS Registry Num- N N ber [7778-66-7] O O O O N N Hypochlorites are derived from hypochlorous O O acid. They are bleaching agents and have large- H H spectrum antimicrobial activity. Calcium hypo- chlorite is used for disinfection in swimming pools and in industrial applications and for pulp 249.1 Suggested Reading and textile bleaching. Sodium hypochlorite is used as household laundry bleach, in commercial Karlberg AT, Skare L, Lindberg I et al (1998) A laundering, in pulp and paper manufacture, in method for quantification of formaldehyde in industrial chemical synthesis, and in the disinfec- the presence of formaldehyde donors in skin- tion of drinking water. Lithium hypochlorite is care products. Contact Dermatitis 38:20–28 used in swimming pools for disinfection and in 114 J.-P. Lepoittevin and C. J. Le Coz

Lachapelle JM, Ale SI, Freeman S et al (1997) 251 Isoeugenol Proposal for a revised international standard series of patch tests. Contact Dermatitis Isoeugenol: CAS Registry Number [97-54-1] 36:121–123 cis-Isoeugenol: CAS Registry Number [5912- Le Coz CJ (2005) Hypersensibilité à la 86-7] Diazolidinyl urée et à l’Imidazolidinyl urée. trans-Isoeugenol: CAS Registry Number Ann Dermatol Venereol 132:587–588 [5932-68-3] Van Hecke E, Suys E (1994) Where next to look Isoeugenol is a mixture of two cis and trans for formaldehyde? Contact Dermatitis 31:268 isomers. It occurs in ylang-ylang and other essen- tial oils. It is a common allergen of perfumes and cosmetics such as deodorants and is contained in 250 Iodopropynyl Butylcarbamate fragrance mix. Its presence in cosmetics is indi- cated in the INGREDIENTS series. Substitution 3-Iodo-2-propynyl-butylcarbamate by esters such as isoeugenyl acetate (not indicated CAS Registry Number [55406-53-6] on the package) does not always resolve the aller- Iodopropynyl butylcarbamate (IPBC) is a genic problem, because of the in vivo hydrolysis broad-spectrum preservative used for years of the substitute into isoeugenol. because of its wide field of application, in polymer emulsions, and pigment dispersions such as OH OH water-based paints and adhesives, cements and O O inks, as a wood preservative, in metalworking fluids, household products, and cosmetics. Aller- gic contact dermatitis to IPBC was reported due to cosmetics, from sanitary wipes, and in metalworkers.

O Cis-Isoeugenol Trans-Isoeugenol

N O

H I 251.1 Suggested Reading

Rastogi SC, Johansen JD, Frosch P et al (1998) 250.1 Suggested Reading Deodorants on the European market: quantita- tive chemical analysis of 21 fragrances. Con- Badreshia S, Marks JG Jr (2002) Iodopropynyl tact Dermatitis 38:29–35 butylcarbamate. Am J Contact Dermat Tanaka S, Royds C, Buckley D et al (2004) Con- 13:77–79 tact allergy to isoeugenol and its derivatives: Bryld LE, Agner T, Rastogi SC et al (1997) problems with allergen substitution. Contact Iodopropynyl butylcarbamate: a new contact Dermatitis 51:288–291 allergen. Contact Dermatitis 36:156–158 Majoie IM, van Ginkel CJW (2000) The biocide iodopropynyl butylcarbamate (IPBC) as an 252 Alpha-Isomethylionone allergen in cutting oils. Contact Dermatitis 43:238–239 3-Buten-2-one, 3-Methyl-4-(2,6,6-trimethyl-2- cyclohexen-1-yl), 3-Methyl-4-(2,6,6-trimethyl-2- cyclohexen-1-yl)-3-buten-2-one, Cetone Alpha CAS Registry Number [127-51-5] Dictionary of Contact Allergens: Chemical Structures, Sources, and References 115

As a fragrance allergen, α-isomethylionone has Lodi A, Mancini LL, Pozzi M et al (1993) Occu- to be mentioned by name in cosmetics within pational airborne allergic contact dermatitis in the EU. parquet layers. Contact Dermatitis 29:281–282

254 Isopropyl Myristate O Tetradecanoic Acid 1-Methyl Ethyl Ester CAS Registry Number [110-27-0] Despite wide use in cosmetics, perfumes, and topical medicaments, isopropyl myristate is a very 252.1 Suggested Reading weak sensitizer and a mild irritant.

Frosch PJ (1998) Are major components of fra- O grances a problem? In: Frosch PJ, Johansen JD, White IR (eds) Fragrances. Beneficial and O adverse effects. Springer, Berlin, pp 92–99 254.1 Suggested Reading

253 Isophorone Diamine Tong PL, Chow ET (2017) Isopropyl myristate contact allergy: could your moisturizer be the 1-Amino-3-aminomethyl-3,3,5-trimethylcyclo- culprit? Contact Dermatitis 77:184–185 hexane, 3-Aminomethyl-3,5,5-trimethylcyclohexy- Uter W, Schnuch A, Geier J et al (2004) Isopropyl lamine myristate recommended for aimed rather than CAS Registry Number [2855-13-2] routine patch testing. Contact Dermatitis Isophorone diamine is widely used in urethane 50:242–244 and epoxy coatings for light-stable, weather-resis- tant properties. It is used in water proofing and paving concreting and in the manufacture of 255 N-Isopropyl-N-Phenyl-4- diisocyanates and polyamides as an epoxy resin Phenylenediamine hardener. It is a strong sensitizer and can cause airborne contact dermatitis. IPPD, N-Isopropyl-N-phenyl-p-phenylenediamine, N-(1-Methylethyl)-N-phenyl-1,4-benzenediamine

NH2 CAS Registry Number [101-72-4] This rubber chemical is used as an antioxidant and antiozonant. The main occupational sources are tires. NH2

H 253.1 Suggested Reading N

Guerra L, Vincenzi, Bardazzi F et al (1992) Con- tact sensitization to isophoronediamine. Con- tact Dermatitis 27:52–53 Kelterer D, Bauer A, Elsner P (2000) Spill- N H induced sensitization to isophorone diamine. Contact Dermatitis 43:110 116 J.-P. Lepoittevin and C. J. Le Coz

255.1 Suggested Reading 18 consecutive patients with contact photo- allergy to ketoprofen: associated photo- Condé-Salazar L, Del-Rio E, Guimaraens D et al allergies to nonbenzophenone-containing (1993) Type IV allergy to rubber additives: a molecules. Contact Dermatitis 48:144–149 10-year study of 686 cases. J Am Acad Hindsen M, Zimerson E, Bruze M (2006) Photo- Dermatol 29:176–180 allergic contact dermatitis from ketoprofen in Lewis VG, Hughes TM, Stone NM (2006) Occu- southern Sweden. Contact Dermatitis pational allergic contact dermatitis to N-isopro- 54:150–157 pyl-N-phenyl-p-phenylenediamine from a Le Coz CJ, Bottlaender A, Scrivener JN et al black rubber “kidney” used in the ceramics (1998) Photocontact dermatitis from industry. Contact Dermatitis 55:250–251 ketoprofen and tiaprofenic acid: cross- Von Hintzenstern J, Heese A, Koch HU et al reactivity study in 12 consecutive patients. (1991) Frequency, spectrum and occupational Contact Dermatitis 38:245–252 relevance of type IV allergies to rubber chemicals. Contact Dermatitis 24:244–252 257 Labetalol

256 Ketoprofen CAS Registry Number [36894-69-6] This beta-adrenergic and alpha-1 blocking CAS Registry Number [22071-15-4] agent caused contact dermatitis and a contact ana- Ketoprofen is an anti-inflammatory drug, used phylactoid reaction during patch testing in a both topically and systemically. It is above all a nurse. photoallergen, responsible for photoallergic or photo-worsened contact dermatitis, with O OH H sun-induced, progressive, severe, and durable reactions. Recurrent photosensitivity is possible N H2N for many years. Photosensitivities are expected to thiophene-phenylketone derivatives such as HO tiaprofenic acid and suprofen, to ketoprofen esters such as piketoprofen, and to benzophenone deriv- atives (see above) such as fenofibrate and 257.1 Suggested Reading benzophenone-3. Concomitant photosensitivities – without clinical relevance – have been observed Bause GS, Kugelman LC (1990) Contact anaphy- to fenticlor, tetrachlorosalicylanilide, triclosan, lactoid response to labetalol. Contact Dermati- tribromsalan, and bithionol. tis 23:51

O 258 Lactucin COOH CAS Registry Number [1891-29-8] Lactucin, as lactucopicrin, is a sesquiterpene lactone contained in lettuce (Lactuca sativa L.).

256.1 Suggested Reading

Durbize E, Vigan M, Puzenat E et al (2003) Spec- trum of cross-photosensitization in Dictionary of Contact Allergens: Chemical Structures, Sources, and References 117

O 259.1 Suggested Reading OH O Bischoff TA, Kelley CJ, Karchesy Y et al (2004) Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. J Ethnopharmacol OH 95:455–457 O

260 Lapachenol 258.1 Suggested Reading CAS Registry Number [573-13-7] Lapachenol is contained in the heartwood of Paulsen E, Andersen KE, Hausen BM (1993) Lapacho wood (Tabebuia avellanedae Lorentz, Compositae dermatitis in a Danish dermatol- Bignoniaceae family). It is a secondary allergen, ogy department in one year (I). Results of after lapachol and deoxylapachol, and likely a routine patch testing with the sesquiterpene prohapten transformed in vivo into a quinone lactone mix supplemented with aimed patch hapten. testing with extracts and sesquiterpene lac- tones of Compositae plants. Contact Dermati- tis 29:6–10 O

259 Lactucopicrin

Intybin CAS Registry Number [6466-74-6] O Lactucopicrin, as lactucin, is a sesquiterpene lactone extracted from various Lactuca spp. and Cichorium intybus L., Asteraceae-Compositae family. 260.1 Suggested Reading

HO Hausen BM (1981) Wood injurious to human health. A manual. De Gruyter, Berlin

O O 261 Lapachol O O 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphth- oquinone, CI 75490, CI Natural Yellow 16 CAS Registry Number [84-79-7] OH Lapachol, a benzoquinone, is a secondary O allergen in teak (Tectona grandis L., Verbenaceae family), a wood largely used for various indoor and outdoor applications (doors, windows, etc.) because of its strong durability. It has similar reactivity to deoxylapachol. 118 J.-P. Lepoittevin and C. J. Le Coz

O a mixture of henna and p-phenylenediamine and its derivatives. Arch Dermatol OH 136:1515–1517 Pasricha JS, Gupta R, Panjwani S (1980) Contact dermatitis to henna (Lawsonia). Contact Der- matitis 6:288–290 O Sukuroglu AA, Battal D, Burgaz S (2017) Moni- toring of Lawsone, p-phenylenediamine and heavy metals in commercial temporary black henna tattoos sold in Turkey. Contact Derma- titis 76:89–95 261.1 Suggested Reading

Estlander T, Jolanki R, Alanko K et al (2001) 263 Lidocaine Occupational allergic contact dermatitis caused by wood dusts. Contact Dermatitis Lidocaine: CAS Registry Number [137-58-6] 44:213–217 Lidocaine Hydrochloride Monohydrate: CAS Lamminpää A, Estlander T, Jolanki R et al (1996) Registry Number [6108-05-0] Occupational allergic contact dermatitis Lidocaine is an anesthetic of the amide group, caused by decorative plants. Contact Dermati- like articaine or bupivacaine. Immediate-type tis 34:330–335 IgE-dependent reactions are rare, and delayed- type contact dermatitis is exceptional. Cross- reactivity between the different amide anesthetics 262 Lawsone is not systematic.

2-Hydroxy-1,4-naphthalenedione, Henna H CAS Registry Number [83-72-7] N Henna, prepared by powdering the dried leaves N of henna plant (Lawsonia inermis L.), is used for O coloring and conditioning hair and nails, particu- larly by Muslims or Hindus. It contains Lawsone, which very rarely induces contact allergy. Most 263.1 Suggested Reading dermatitis caused by “black henna” is due to PPD and derivatives. Duque S, Fernandez L (2004) Delayed hypersen- sitivity to amide local anesthetics. Allergol O Immunopathol (Madr) 32:233–234 Halabi-Tawil, Kechichian E, Tomb R (2016) An OH unusual complication of minor surgery: con- tact dermatitis caused by injected lidocaine. Contact Dermatitis 75:253–255 Waton J, Boulanger A, Trechot PH et al (2004) O Contact urticaria from Emla® cream. Contact Dermatitis 51:284–287 262.1 Suggested Reading

Le Coz CJ, Lefebvre C, Keller F et al (2000) Allergic contact dermatitis caused by skin painting (pseudotattooing) with black henna, Dictionary of Contact Allergens: Chemical Structures, Sources, and References 119

® 264 Lilial Meding B, Barregard L, Marcus K (1994) Hand eczema in car mechanics. Contact Dermatitis See p-tert-Butyl-alpha-methylhydrocinnamic 30:129–134 aldehyde. Pesonen M, Suomela S, Kuuliala O et al (2014) Occupational contact dermatitis caused by d- limonene. Contact Dermatitis 71:273–279 265 Limonene

Limonene – d-limonene + l-limonene: CAS Reg- 266 Linalool istry Number [138-86-3] d-limonene – (+)-limonene, R-limonene, 3,7-Dimethyl-1,6-octadien-3-ol, Linalyl Alcohol, α-limonene, (R)- p-Mentha-1,8-diene, Dipentene, 2,6-Dimethyl-2,7-octadien-6-ol Carvene, Citrene: CAS Registry Number [5989- CAS Registry Number [78-70-6] 27-5] Linalool is a terpene chief constituent of l-limonene – ()-limonene, S-limonene, linaloe oil, also found in oils of Ceylon cinnamon, β-Limonene, 4-(S)-1-Methyl-4-(1-methylethenyl)- sassafras, orange flower, bergamot, Artemisia cyclohexene: CAS Registry Number [5989-54-8] balchanorum, and ylang-ylang. This frequently Limonene is a racemic form of d- and used scented substance is a sensitizer by the way l-limonene. d-limonene is contained in Citrus spe- of primary or secondary oxidation products. As a cies such as citrus, orange, mandarin, and berga- fragrance allergen, linalool has to be mentioned mot. l-limonene is contained in Pinus pinea. The by name in cosmetics within the EU. racemic form (d- and l-limonene) is also named dipentene. d-limonene, used as a solvent, may be OH found in cleansing or in degreasing agents. Its sensitizing potential increases with prolonged air contact, which induces oxidation and leads to oxidation products. The presence of d-limonene has to be mentioned by name in cosmetics of the EU.

266.1 Suggested Reading

Christensson JB, Karlberg A-T, Andersen KE et al (2016) Oxidized limonene and oxidized linal- d-limonene l-limonene ool – concomitant contact allergy to common fragrance terpenes. Contact Dermatitis 74:273–280 265.1 Suggested Reading Kanerva L, Estlander T, Jolanki R (1995) Occu- pational allergic contact dermatitis caused by Karlberg AT, Dooms-Goossens A (1997) Contact ylang-ylang oil. Contact Dermatitis allergy to oxidized d-limonene among derma- 33:198–199 – titis patients. Contact Dermatitis 36:201 206 Skold M, Borje A, Harambasic E et al (2004) Karlberg AT, Magnusson K, Nilsson U (1992) Air Contact allergens formed on air exposure of oxidation of d-limonene (the citrus solvent) linalool. Identification and quantification of creates potent allergens. Contact Dermatitis primary and secondary oxidation products – 26:332 340 and the effect on skin sensitization. Chem Res Toxicol 17:1697–1705 120 J.-P. Lepoittevin and C. J. Le Coz

267 Linalyl Acetate 268.1 Suggested Reading

CAS Registry Number [115-95-7] Vilaplana J, Romaguera C, Grimalt F (1991) Con- Structurally close to linalool, linalyl acetate is tact dermatitis from lincomycin and spectino- the main component of lavender oil and is com- mycin in chicken vaccinators. Contact monly used in fragrances and toiletries and in Dermatitis 24:225–226 household cleaners and detergents as well. By autoxidation, it leads mainly to hydroperoxides, with a high sensitizing potent. 269 Lindane

γ OAc -1,2,3,4,5,6-Hexachlorocyclohexane CAS Registry Number [58-89-9] Lindane is a pesticide used for its antiinsect properties in agriculture, wood protection, in anti- insect paints, and veterinary and human medicine against many insects such as spiders, mosquitoes, ticks, scabies, lice, and demodicidosis. Its use is 267.1 Suggested Reading controlled, particularly because of neurological toxicity. Sköld M, Hagvall L, Karlberg AT (2008) Autox- idation of linalyl acetate, the main component Cl of lavender oil, creates potent contact aller- Cl Cl gens. Contact Dermatitis 58:9–14

Cl Cl 268 Lincomycin (Hydrochloride Monohydrate) Cl

Lincomycin: CAS Registry Number [154-21-2] 269.1 Suggested Reading Lincomycin hydrochloride monohydrate: CAS Registry Number [7179-49-9] Sharma VK, Kaur S (1990) Contact sensitization Lincomycin is an antibiotic of the lincosanide by pesticides in farmers. Contact Dermatitis – group, active against Gram-positive bacteria. 23:77 80 Occupational exposure occurs in poultry and pig breeders. 270 Lyral®

See Hydroxymethylpentacyclohexenecarboxal- N O dehyde. OH

HN 271 Malathion OH OH Carbetox, Carbofos, Chemathion, Cimexan, S Dorthion, Extermathion, Fosfotion OH CAS Registry Number [121-75-5] This organophosphorus pesticide is used as an insecticide and an acaricide, particularly against head lice. Sensitization was reported in farmers. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 121

O 5 fungicides in a vineyard worker. Cross- reactions between fungicides of the dithiocar- – S O bamate group? Contact Dermatitis 34:324 329

P O O S 273 Maneb O O Ethylenebisdithiocarbamate Manganese CAS Registry Number [12427-38-2] 271.1 Suggested Reading Maneb is a pesticide with fungicide properties, belonging to the dithiocarbamate group. Sensiti- O’Malley M, Rodriguez P, Maibach HI (1995) zation occurs mainly in farmers and agricultural Pesticide patch testing: California nursery workers. workers and controls. Contact Dermatitis 32:61–62 H S Sharma VK, Kaur S (1990) Contact sensitization S N by pesticides in farmers. Contact Dermatitis Mn N S 23:77–80 S H n

272 Mancozeb 273.1 Suggested Reading Zinc Manganese Ethylenebisdithiocarbamate CAS Registry Number [8018-01-7] Crippa M, Misquith L, Lonati A et al (1990) Mancozeb is a fungicide of the ethylene-bis- Dyshidrotic eczema and sensitization to dithio- fl dithiocarbamate group. It is present in Rondo-M® in a orist. Contact Dermatitis – with pyrifenox. Occupational exposure occurs 23:203 204 mainly in agricultural workers, in vineyard Koch P (1996) Occupational allergic contact der- workers, or in florists. matitis and airborne contact dermatitis from 5 fungicides in a vineyard worker. Cross- reactions between fungicides of the dithiocar- H S bamate group? Contact Dermatitis 34:324–329 S N Zn2+ O’Malley M, Rodriguez P, Maibach HI (1995) Mn N S Y Pesticide patch testing: California nursery S H X workers and controls. Contact Dermatitis 32:61–62 Peluso AM, Tardio M, Adamo F et al (1991) 272.1 Suggested Reading Multiple sensitization due to bis-dithiocarbamate and thiophthalimide pesti- Crippa M, Misquith L, Lonati A et al (1990) cides. Contact Dermatitis 25:327 Dyshidrotic eczema and sensitization to dithio- Sharma VK, Kaur S (1990) Contact sensitization fl carbamates in a orist. Contact Dermatitis by pesticides in farmers. Contact Dermatitis – 23:203 204 23:77–80 Iliev D, Elsner P (1997) Allergic contact from the fungicide Rondo-M® and the insecticide Alfacron®. Contact Dermatitis 36:51 Koch P (1996) Occupational allergic contact der- matitis and airborne contact dermatitis from 122 J.-P. Lepoittevin and C. J. Le Coz

274 Melamine and Melamine- metal industry, homemakers, health services and Formaldehyde Resins laboratories, the building industry, and shoe- makers. It is also used as a corrosion inhibitor in Melamine: 2,4,6-Triaminotriazine cutting fluids or in releasing fluids in the pottery CAS Registry Number [108-78-1] industry. Melamine-formaldehyde resin (MFR) results from condensation of melamine and formalde- N hyde. It is an active ingredient of strong SH (reinforced) plasters, such as industrial or some S dental plasters used for molding. It is also used as a textile finish resin. MFR acts as an allergen generally because of formaldehyde releasing. 275.1 Suggested Reading

H NNNH 2 2 Condé-Salazar L, Del-Rio E, Guimaraens D et al (1993) Type IV allergy to rubber additives: a N N 10-year study of 686 cases. J Am Acad Dermatol 29:176–180 Mancuso G, Reggiani M, Berdondini RM (1996) NH2 Occupational dermatitis in shoemakers. Con- tact Dermatitis 34:17–22 274.1 Suggested Reading Tomc C, Kwasniak L, Shoureshi P et al (2012) Allergic contact dermatitis probably caused by Aalto-Korte K, Jolanki R, Estlander T (2003) mercaptobenzothiazole in thermal undergar- – Formaldehyde-negative allergic contact der- ments. Contact Dermatitis 66:293 295 matitis from melamine-formaldehyde resin. Von Hintzenstern J, Heese A, Koch HU et al Contact Dermatitis 49:194–196 (1991) Frequency, spectrum and occupational Garcia Bracamonte B, Ortiz de Frutos FJ, Iglesias relevance of type IV allergies to rubber – Diez L (1995) Occupational allergic contact chemicals. Contact Dermatitis 24:244 252 dermatitis due to formaldehyde and textile fin- Wilkinson SM, Cartwright PH, English JSC ish resins. Contact Dermatitis 33:139–140 (1990) Allergic contact dermatitis from fl Lewis FM, Cork MJ, McDonagh AJG et al (1993) mercaptobenzothiazole in a releasing uid. Allergic contact dermatitis from resin- Contact Dermatitis 23:370 reinforced plaster. Contact Dermatitis 28:40–41 Rustemeyer T, Frosch PJ (1996) Occupational 276 Mercaptobenzothiazole Salts skin diseases in dental laboratory technicians. (I). Clinical picture and causative factors. Con- Mercaptobenzothiazole, Sodium Salt: CAS Reg- tact Dermatitis 34:125–133 istry Numbers [2492-26-4] Mercaptobenzothiazole, Zinc Salt: CAS Reg- istry Numbers [155-04-4] 275 Mercaptobenzothiazole Such mercaptobenzothiazole hydrosoluble salts are used as antioxidants and biocides in fl 2-Mercaptobenzothiazole, MBT cutting uids and greases, paints, or glues. CAS Registry Number [149-30-4] MBT is a rubber chemical, accelerant of vul- canization, and contained in “mercapto mix.” The most frequent occupational categories are the Dictionary of Contact Allergens: Chemical Structures, Sources, and References 123

N - + N S Zn2 OH - + S . Na S S 2

276.1 Suggested Reading 278.1 Suggested Reading Le Coz CJ (2004) Fiche d’éviction en cas d’hypersensibilité au mercaptobenzothiazole Clerx V, van den Keybus C, Kochuyt A et al et au mercapto mix. Ann Dermatol Venereol (2003) Drug intolerance reaction to insulin 131:1012–1014 therapy caused by metacresol. Contact Derma- titis 48:162–163 277 MESNA 279 Metanil Yellow Sodium 2-Mercaptoethane Sulfonate CAS Registry Number [19767-45-4] Acid Yellow 36, CI 13065 Mesna is used as a mucolytic agent and as an CAS Registry Number [587-98-4] antidote to chloro-acetyl-aldehyde and acrolein Metanil yellow is a yellow monoazoic dye. (a bladder toxic metabolite of ifosfamide or cyclo- This coloring agent is used in leather and wood phosphamide). It has been reported as a cause of stains and is also employed as a food dye in India. occupational allergic (hand and airborne) derma- titis in nurses. H

O N + -

Na O S H N NaO3S S N O

277.1 Suggested Reading 279.1 Suggested Reading Benyoussef K, Bottlaender A, Pfister HR et al (1996) Allergic contact dermatitis from Hausen BM (1994) A case of allergic contact mesna. Contact Dermatitis 34:228–229 dermatitis due to metanil yellow. Contact Der- Kiec-Swierczynska M, Krecisz B (2003) Occupa- matitis 31:117–118 tional airborne allergic contact dermatitis from mesna. Contact Dermatitis 48:171 280 Methenamine

278 Metacresol Hexamethylenetetramine CAS Registry Number [100-97-0] 3-Cresol, 3-Methylphenol, m-Cresol Hexamethylenetetramine is used in the CAS Registry Number [108-39-4] foundry, tire and rubber, and phenol formalde- Metacresol is contained as a preservative in hyde resins industries and in other applications almost all human insulin. It has been reported as such as a hardener in epoxy resins bisphenol A a cause of allergic reaction due to injected insulin. type and as an anticorrosive agent. It is an 124 J.-P. Lepoittevin and C. J. Le Coz ammonia and formaldehyde releaser sometimes 282 Methiocarb used in topical medicaments and cosmetics. 3,5-Dimethyl-4-(methylthio)phenol N methylcarbamate, Mesurol CAS Registry Number [2032-65-7] N N Methiocarb is an insecticide or molluscicide N with a cholinesterase inhibiting effect. A case of contact dermatitis was reported in a carnation grower. 280.1 Suggested Reading H Gonzalez-Perez R, Gonzalez-Hermosa R, Aseginolaza B et al (2003) Allergic contact O N dermatitis from methenamine in an antiperspi- rant spray. Contact Dermatitis 49:266 O Holness DL, Nethercott JR (1993) The perfor- S mance of specialized collections of bisphenol A epoxy resin system components in the eval- uation of workers in an occupational health clinic population. Contact Dermatitis 282.1 Suggested Reading 28:216–219 Willems PWJM, Geursen-Reitsma AM, van Joost T (1997) Allergic contact dermatitis due to 281 Methidathion methiocarb (Mesurol). Contact Dermatitis 36:270 Somonil, Supracid, Suprathion, Ultracid CAS Registry Number [950-37-8] Methidation is an organophosphorus com- 283 Methomyl pound used as an insecticide. Cross-sensitivity was described to dichlorvos. S-Methyl-N-(methylcarbamoyloxy)-thioacetimidate, Lannate CAS Registry Number [16752-77-5] S O O Methomyl is a pesticide agent, a carbamate P insecticide with anticholinesterase activity. This O S N mixture of two stereoisomers is used as a foliar S spray to control field crops, in stables and poultry N houses, and in glasshouses on ornamentals and vegetables, or in flypapers. Cases were reported O in chrysanthemum growers and in two women working in a plant nursery.

281.1 Suggested Reading O S N Ueda A, Aoyama K, Manda F et al (1994) O N Delayed-type allergenicity of triforine H (Saprol®). Contact Dermatitis 31:140–145 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 125

283.1 Suggested Reading International Nomenclature of Cosmetics Ingredi- ents (INCI) inventory system. It belongs to the Bruynzeel DP (1991) Contact sensitivity to chemical class of alkoxylated alcohols. It is uti- Lannate®. Contact Dermatitis 25:60–61 lized as an emulsion stabilizer, a skin- conditioning, and a viscosity-increasing agent in cosmetics. 284 (R)-4-Methoxy Dalbergione

CAS Registry Numbers [4640-26-0] and [28396- O O 75-0] O H (R)-4-Methoxy dalbergione is the main aller- gen of Dalbergia nigra All. (Brazilian rosewood, x palissander) and Dalbergia latifolia Roxb. (East Indian rosewood). Occupational sensitization occurs in timber workers.

O

y

O

O 285.1 Suggested Reading

Le Coz CJ, Heid E (2001) Allergic contact der- 284.1 Suggested Reading matitis from methoxy PEG-17/dodecyl glycol copolymer (Elfacos® OW 100). Contact Der- Gallo R, Guarrera M, Hausen BM (1996) Air- matitis 44:308–309 borne contact dermatitis from East Indian rose- wood (Dalbergia latifolia Roxb.). Contact Dermatitis 35:60–61 286 Methoxypsoralens Hausen BM (2000) Woods. In: Kanerva L, Elsner P, Wahlberg JE, Maibach HI (eds) 5-Methoxypsoralen, Bergapten(e): CAS Registry Handbook of occupational dermatology. Number [484-20-8] Springer, Berlin/Heidelberg/New York, pp 8-Methoxypsoralen, Methoxsalen, Meladinin, 771–780 Xanthotoxin: CAS Registry Number [298-81-7] These fur(an)ocoumarins are phototoxic com- pounds that cause phototoxic dermatitis. Many 285 Methoxy PEG-17/Dodecyl plants of the Apiaceae-Umbelliferae and most of Glycol Copolymer the Rutaceae family contain 5-methoxypsoralen and 8-methoxypsoralen. Their spectra are in the CAS Registry Number [88507-00-0] UVA range (300–360 nm). They are used in com- Methoxy PEG-17/dodecyl glycol copolymer is bination with UVA to treat various skin disorders one of the numerous copolymers recorded in the such as psoriasis. 126 J.-P. Lepoittevin and C. J. Le Coz

O 288 Methyl-2,3-Epoxy-3- (4-Methoxyphenyl)Propionate

3-(-Methoxyphenyl)glycidic acid methylester, O O O O O O Methyl 3-(p-methoxyphenyl)oxirane-2-carboxylate 5-MOP O 8-MOP CAS Registry Number [42245-42-1] Methyl 2,3 epoxy-3-(4-methoxyphenyl)propi- onate is an intermediate product in the synthesis of 286.1 Suggested Reading diltiazem hydrochloride. Contact dermatitis was observed in several laboratory technicians. Ena P, Camarda I (1990) Phytophotodermatitis from Ruta corsica. Contact Dermatitis 22:63 O Ena P, Cerri R, Dessi G, Manconi PM, Atzei AD O (1991) Phototoxicity due to Cachrys libanotis. Contact Dermatitis 24:1–5 O

287 Methyl Aminolevulinate

O CAS Registry Number [33320-16-0] Methyl aminolevulinate is sued as a photosen- sitizer for the treatment of non-melanoma skin cancers by photodynamic therapy. 288.1 Suggested Reading

O Rudzki E, Rebandel P (1990) Dermatitis from methyl 2,3 epoxy-3-(4-methoxyphenyl)propi- H2N OCH3 onate. Contact Dermatitis 23:382 O

289 Methyl Gallate 287.1 Suggested Reading CAS Registry Number [99-24-1] Al Malki A, Marguery M-C, Giordano-Labadie F This ester of gallic acid is used as an antioxi- et al (2017) Systemic allergic contact dermati- dant agent. A case was reported by using a reprog- tis caused by methyl aminolaevulinate in a raphy paper. patient with keratosis-ichthyosis-deafness syn- – drome. Contact Dermatitis 76:190 192 OH Jungersted JM, Dam TN, Bryld LE et al (2008) Allergic reactions to Metvix (ALA-ME). Con- HO OH tact Dermatitis 58:184–186 Korshøj S, Sølvsten H, Erlandsen M et al (2009) Frequency of sensitization to methyl aminolae- vulinate after photodynamic therapy. Contact – Dermatitis 60:320 324 O O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 127

289.1 Suggested Reading O

Degos R, Lépine J, Akhoundzadeh H (1968) O Sensibilisation cutanée due à la manipulation de papier reprographie. Bull Soc Fr Dermatol 75:595–596

290 Methyl Heptine Carbonate 291.1 Suggested Reading Methyl oct-2-ynoate, Methyl 2-octynoate, Folione English JS, Rycroft RJ (1988) Allergic contact CAS Registry Number [111-12-6] dermatitis from methyl heptine and methyl This perfumed molecule belongs to the list of octine carbonates. Contact Dermatitis 26 allergens that have to be indicated by name on 18:174–175 the ingredients list of cosmetics in the EU. Active sensitization to this chemical have been reported. 292 Methyl Salicylate O CAS Registry Number [119-36-8] O This anti-inflammatory agent is found in a wide number of ointments and can induce allergic contact dermatitis.

O 290.1 Suggested Reading O English JS, Rycroft RJ (1988) Allergic contact dermatitis from methyl heptine and methyl OH octine carbonates. Contact Dermatitis 18:174–175 Heisterberg MV, Vigan M, Johansen JD (2010) 292.1 Suggested Reading Active sensitization and contact allergy to methyl 2-octynoate. Contact Dermatitis Hindson C (1977) Contact eczema from methyl – 62:97 101 salicylate reproduced by oral aspirin (acetyl ). Contact Dermatitis 3:348–349 Oiso N, Fulai K, Ishii M (2004) Allergic contact 291 Methyl Octine Carbonate dermatitis due to methyl salicylate in a com- press. Contact Dermatitis 51:34–35 Methyl non-2-ynoate, Methyl 2-nonynoate Registry Number [111-80-8] This perfumed molecule is related to methyl heptine carbonate. Cross-reactivity is frequent. 128 J.-P. Lepoittevin and C. J. Le Coz

293 Methyl-Terpyridine 295 Methylchloroisothiazolinone

2,2:6,2,-(4-Methyl)-ter-pyridine), 4-Methyl Chloromethylisothiazolinone, 5-Chloro-2-me- (2,2,2-terpyridine) thyl-4-isothiazolin-3-one, MCI CAS Registry Number for 2,2,2-Terpyridine CAS Registry Number [26172-55-4] [1148-79-4] MCI is mainly associated with methylisothia- This molecule is a terpyridine with a 4-methyl zolinone for its bactericidal and fongistatic prop- substitution. A case of occupational dermatitis erties. It is found in Kathon® CG or derivatives. was reported in a chemical technician with no MCI is found in water-based products such as cross-reactivity to pyridine derivatives. cosmetics, paints, and glues. Pure MCI is highly irritant and may cause active sensitization.

O

N N Cl S N N

295.1 Suggested Reading 293.1 Suggested Reading Isaksson, Persson L (2015) Occupational contact Le Coz CJ, Caussade P, Bottlaender A (1998) dermatitis caused by methylchloroisothia- Occupational contact dermatitis from methyl- zolinone/methylisothiazolinone through expo- fi ter-pyridine in a chemistry laboratory techni- sure to ller dust containing this preservative cian. Contact Dermatitis 38:214–215 and with a positive patch rest reaction to the dust. Contact Dermatitis 73:119–120 Nielsen H (1994) Occupational exposure to iso- 294 2-Methyl-4,5-Trimethylene-4- thiazolinones. A study based on a product reg- Isothiazolin-3-one ister. Contact Dermatitis 31:18–21 Schubert H (1997) Airborne contact dermatitis CAS Registry Number [82633-79-2] due to methylchloro- and methylisothia- This biocide induced contact dermatitis in a zolinone (MCI/MI). Contact Dermatitis 36:274 laboratory technician, also sensitive to the other Tay P, Ng SK (1994) Delayed skin burns from isothiazolinone BIT. MCI/MI biocide used in water treatment. Con- tact Dermatitis 30:54–55 O 296 Methylchloroisothiazolinone N + Methylsiothiazolinone S (MCI/MI)

CAS Registry Numbers [55965-84-9] and 294.1 Suggested Reading [96118-96-6] Kathon® CG (CG = cosmetic grade) is a 3:1 ’ Burden AD, O Driscoll JB, Page FC et al (1994) mixture of CMI and MI, at a 1.5% concentration. Contact hypersensitivity to a new iso- It is used for cosmetics and toiletries, metalwork- – thiazolinone. Contact Dermatitis 30:179 180 ing fluids, or paints, in which it can be added only Dictionary of Contact Allergens: Chemical Structures, Sources, and References 129 periodically or in color film developers. Kathon® 297 Methyldibromoglutaronitrile 886 MW (MW = metalworking fluids) is a mix- ture CMI/MI mixture at a 13.9% concentration, 1,2-Dibromo 2,4-Dicyanobutane mainly contained in metalworking fluids. CAS Registry Number [35691-65-7] Kathon® FP 1.5 contains MCI/MI at 1.5% con- Methyldibromoglutaronitrile is a biocide centration in propylene glycol. Kathon® LX widely used as a preservative agent in cosmetics, (LX = LateX) contains MCI/MI at a tenfold con- toiletries, and metalworking fluids. It is a potent centration of Kathon® CG. Kathon® WT allergen, banned in all cosmetics in the EU (WT = water treatment) is a MCI/MI mixture since 2007. used in the paper industry. Parmetol® K40, Parmethol® DF 12 and Parmetol® DF CN 35, Parmetol® A 23, Parmetol® K50, and Parmetol® DF 18 are other brand names of MCI/MI.

O Br Br CN O

N 297.1 Suggested Reading N S Cl S Aalto-Korte K, Jolanki R, Estlander T et al (1996) Occupational allergic contact dermatitis caused by Euxyl K 400. Contact Dermatitis 296.1 Suggested Reading 35:193–194 Le Coz CJ (2005) Hypersensibilité au méthyldi- Björkner B, Bruze M, Dahlquist I et al (1986) bromoglutaronitrile (Dibromodicyanobutane). ® Contact allergy to the preservative Kathon Ann Dermatol Venereol 132:496–497 – CG. Contact Dermatitis 14:85 90 Marcano ME, Heras F, Conde-Salazar L (2007) Fernandez de Corres L, Navarro JA, Gastaminza Occupational allergic contact dermatitis to G et al (1995) An unusual case of sensitization methyldibromoglutaronitrile in hand to methylchloro- and methyl-isothiazolinone degreasing toilet paper. Contact Dermatitis (MCI/MI). Contact Dermatitis 33:215 57:126–127 Isaksson, Persson L (2015) Occupational contact dermatitis caused by methylchloroisothia- zolinone/methylisothiazolinone through expo- 298 Methylhexahydrophthalic sure to filler dust containing this preservative Anhydride and with a positive patch rest reaction to the – dust. Contact Dermatitis 73:119 120 1,3-Isobenzofurandione, Hexahydromethyl Pazzaglia M, Vincenzi C, Gasparri F et al (1996) CAS Registry Numbers [19438-60-9] [39363- Occupational hypersensitivity to iso- 62-7], [86403-41-0], and [95032-44-3] thiazolinone derivatives in a radiology techni- Methylhexahydrophthalic anhydride is an – cian. Contact Dermatitis 34:143 144 epoxy hardener, irritant to skin and mucous mem- branes. It is included in nondiglycidyl-ether-of- bisphenol A epoxy resins. It can induce both allergic contact dermatitis and immunologic con- tact urticaria. It is structurally close to 130 J.-P. Lepoittevin and C. J. Le Coz methyltetrahydrophthalic anhydride, which can Schwensen JF, Menné T, Friis UT et al (2015) also cause sensitization. Undisclosed methylisothiazolinone in wet wipes for occupational use causing occupa- O tional allergic contact dermatitis in a nurse. Contact Dermatitis 73:182–184

O 300 Methylol Phenols

O 2-Methylol Phenol – 2-Hydroxymethyl-Phenol: CAS Registry Number [90-01-7] – 298.1 Suggested Reading 3-Methylol Phenol 3-Hydroxymethyl-Phe- nol, 3-Hydroxybenzyl Alcohol: CAS Registry Aalto-Korte K, Pesonen M, Suuronen K (2015) Number [620-24-6] – Occupational allergic contact dermatitis 4-Methylol Phenol 4-Hydroxymethyl-Phe- caused by epoxy chemicals: occupations, sen- nol: CAS Registry Number [623-05-2] sitizing products and diagnosis. Contact Der- Methylol phenols are sensitizers contained in matitis 73:336–342 resins based on phenol and formaldehyde of the Kanerva L, Jolanki R, Estlander T (1997) Allergic resol type. Cross-reactivity is possible with other contact dermatitis from non-diglycidyl-ether- phenol-derivative molecules. of-bisphenol-A epoxy resins. Contact Derma- titis 36:34–38 OH OH OH OH

299 Methylisothiazolinone OH 2-MP 3-MP 4-MP 2-Methyl-4-isothiazolin-3-one, MI OH CAS Registry Number [2682-20-4] MI is generally associated with MCI, in Kathon® CG, MCI/MI, and Euxyl® K 100. This 300.1 Suggested Reading preservative is currently used in water-based products such as cosmetics, paints, and glues. Bruze M, Zimerson E (1997) Cross-reaction pat- Skin contact with concentrated solution can terns in patients with contact allergy to simple cause severe irritant dermatitis. methylol phenols. Contact Dermatitis 37:82–86 O Bruze M, Fregert S, Zimerson E (1985) Contact allergy to phenol-formaldehyde resins. Contact Dermatitis 12:81–86 N S 301 1-Methylpyrrolidone

299.1 Suggested Reading N-Methyl-2-pyrrolidone, 1-Methyl-2-pyrrolidone CAS Registry Number [872-50-4] Schubert H (1997) Airborne contact dermatitis 1-Methylpyrrolidone is an aprotic solvent with due to methylchloro- and methylisothia- a wide range of applications: petrochemical pro- zolinone (MCI/MI). Contact Dermatitis 36:274 cessing, surface coating, dyes and pigments, Dictionary of Contact Allergens: Chemical Structures, Sources, and References 131 industrial and domestic cleaning compounds, and 302.1 Suggested Reading agricultural and pharmaceutical formulations. It is mainly an irritant, but it can cause severe contact Liden C, Brehmer-Andersson E (1988) Occupa- dermatitis due to prolonged contact. tional dermatoses from color developing agents. Clinical and histopathological observa- tions. Acta Derm Venereol (Stockh) 68:514–522 N O Scheman AJ, Katta R (1997) Photographic aller- gens: an update. Contact Dermatitis 37:130

303 Metronidazole (Hydrochloride) 301.1 Suggested Reading CAS Registry Number [443-48-1] (CAS Registry Jungbauer FH, Coenraads PJ, Kardaun SH (2001) Number [69198-10-3]) Toxic hygroscopic contact reaction to N- Metronidazole is a nitro-5-imidazole com- methyl-2-pyrrolidone. Contact Dermatitis pound with antiprotozoal and antibacterial prop- 45:303–304 erties. Topical exposure may induce allergic Leira H, Tiltnes A, Svendsen K, Vetlesen L (1992) contact dermatitis. Sensitization is mainly Irritant cutaneous reactions to N-methyl-2- observed with the treatment of rosacea and rarely pyrrolidone (NMP). Contact Dermatitis occurs from handling of tablets in nurses. Sys- 27:148–150 temic intake may provoke fixed drug eruption.

N 302 Metol (Sulfate) HCl H3C N NO2 4-(Methylamino)phenol: CAS Registry Number [150-75-4] 4-(Methylamino)phenol Sulfate: CAS Regis- OH try Numbers [1936-57-8] (unspecified sulfate), [51-72-9] (sulfate[1:1]), and [55-55-0] (sulfate [2:1]) 303.1 Suggested Reading Metol is contained in black and white film developers and caused contact dermatitis in Madsen JT, Thormann J, Kerre S et al (2007) photographers. Allergic contact dermatitis to topical metroni- dazole – 3 cases. Contact Dermatitis OH 56:364–366 Madsen JT, Lorentzen HF, Paulsen E (2009) Con- tact sensitization to metronidazole from possi-

(.H2SO4) ble occupational exposure. Contact Dermatitis 60:117–118 Vila JB, Bernier MA, Gutierrez JV et al (2002) N Fixed drug eruption caused by metronidazole. H Contact Dermatitis 46:122 132 J.-P. Lepoittevin and C. J. Le Coz

304 Mevinphos 305.1 Suggested Reading

CAS Registry Number [7786-34-7] Keller K, Schwanitz HJ (1992) Combined imme- Sensitization to mevinphos (also named diate and delayed hypersensitivity to Duraphos, Phosdrin, and Phosfene), an organo- mezlocillin. Contact Dermatitis 27:348–349 phosphate cholinesterase inhibitor that is used as an insecticide, was rarely reported. 306 Monoethanolamine

O O O Ethanolamine, 2-Aminoethanol P CAS Registry Number [141-43-5] O O Monoethanolamine is contained in many prod- ucts, such as metalworking fluids. It is mainly an irritant. Traces may exist in other ethanolamine fluids. 304.1 Suggested Reading

H2N Jung HD, Ramsauer E (1987) Akute Pesticid- OH Intoxication kombiniert mit epicutaner Sensibilisierung durch den organischen 306.1 Suggested Reading Phosphorsäureester Mevinphos (PD5). Aktuel Dermatol 13:82–83 Bhushan M, Craven NM, Beck MH (1998) Con- tact allergy to 2-aminoethanol (mono- ethanolamine) in a soluble oil. Contact 305 Mezlocilin Dermatitis 39:321 Ulrich S, Skudlik C, John SM (2007) CAS Registry Number [51481-65-3] Occupatiuonal allergic contact dermatitis Mezlocillin sodium salt monohydrate: CAS from monoethanolamine in a dental nurse. Registry Number [59798-30-0] Contact Dermatitis 56:292–293 Mezlocillin is an acylaminopenicillin, which caused both immediate and delayed hypersensi- tivity in a nurse. 307 Morphine (Morphine Hydrochloride, Morphine O O O H Tartrate) O N S N N O CAS Registry Number [57-27-2] (CAS Registry Number [52-26-6], CAS Registry Number

N S [302-31-8]) H Morphine bitartrate caused contact dermatitis N in a worker at a plant producing opium alkaloids. O Morphine hydrochloride and morphine bitartrate COOH showed patch-test-positive reactions in another patient with contact dermatitis working in the production of concentrated poppy straw. We observed a concomitant reaction between a Dictionary of Contact Allergens: Chemical Structures, Sources, and References 133 morphine base and a codeine base in a patient with 309 Morpholinyl drug skin eruption due to codeine. Mercaptobenzothiazole

HO 2-(4-Morpholinylthiobenzothiazole), 2-Morpholin Benzothiazyl Sulfenamide, Benzothiazole, 2-(4-Morpholinylthio) CAS Registry Number [102-77-2] O H This rubber vulcanization accelerator belongs to the mercaptobenzothiazole-sulfenamide group. N It is used as a chemical in the rubber industry, especially in the production of synthetic rubber HO articles. It is contained in “mercapto mix.” As a corrosion inhibitor, it can be found in cutting fluids or in releasing fluids in the pottery industry. 307.1 Suggested Reading It induces mainly delayed-type hypersensitivity, but a case of immediate-type hypersensitivity was Condé-Salazar L, Guimaraens D, Gonzalez M reported in a dental assistant. et al (1991) Occupational allergic contact der- matitis from opium alkaloids. Contact Derma- N titis 25:202–203 Hvid L, Svendsen MT, Andersen KE (2016) S Occupational allergic contact dermatitis S N caused by heroin (diacetylmorphine) and mor- phine. Contact Dermatitis 74:301–302 O

308 4-Morpholinyl-2-Benzothiazyle 309.1 Suggested Reading Disulfide Brehler R (1996) Contact urticaria caused by latex-free nitrile gloves. Contact Dermatitis 2-(Morpholinodithio)benzothiazole, Benzothiazole, 34:296 2-(4-morpholinyldithio) Condé-Salazar L, Del-Rio E, Guimaraens D et al CAS Registry Number [95-32-9] (1993) Type IV allergy to rubber additives: a This chemical is a mercaptobenzothiazole- 10-year study of 686 cases. J Am Acad sulfenamide compound, used as moderate accel- Dermatol 29:176–180 erator in rubber vulcanization. Le Coz CJ (2004) Fiche d’éviction en cas d’hypersensibilité au mercaptobenzothiazole N et au mercapto mix. Ann Dermatol Venereol S 131:846–848 S SN O

310 Naled 308.1 Suggested Reading CAS Registry Number [300-76-5] Le Coz CJ (2004) Fiche d’éviction en cas Naled is an organophosphate cholinesterase d’hypersensibilité au mercaptobenzothiazole inhibitor that is used as an insecticide and acari- et au mercapto mix. Ann Dermatol Venereol cide. Sensitization seems to be very rare. 131:1012–1014 134 J.-P. Lepoittevin and C. J. Le Coz

O Br dyed clothing. It has been indirectly reported as a CI cause of occupational allergy due to its coupling P CI O O with Diazo Component 51 or as a cross-sensitizer O or sensitizer associated with Pigment Red 23 in Br red parts of tattoos. Pigmented contact dermatitis is usual in patients with a high phototype.

310.1 Suggested Reading OH H Edmundson WF, Davies JE (1967) Occupational N dermatitis from naled. Arch Environ Health – 15:89 91 O Mick DL, Gartin TD, Long KR (1970) A case report: occupational exposure to the insecticide naled. J Iowa Med Soc 60:395–396 312.1 Suggested Reading

311 1-Naphthol Le Coz CJ, Lepoittevin JP (2001) Clothing der- matitis from Naphthol AS. Contact Dermatitis – Alpha-Naphthol, CI 76605, CI Oxidation Base 33 44:366 367 CAS Registry Number [90-15-3] Roed-Petersen J, Batsberg W, Larsen E (1990) Alpha-naphthol can be used in dye manufac- Contact dermatitis from Naphthol – ture and is classified as a hair dye. Combined with AS. Contact Dermatitis 22:161 163 epichlorhydrin and NaOH to form alpha-naphthyl glycidyl ether, it caused sensitization in one of three workers in a chemical plant. 313 Neomycin (Neomycin B Hydrochloride, Neomycin B Sulfate) OH

Framycetin, Soframycin® CAS Registry Number [1404-04-2] (CAS Registry Number [25389-99-5], CAS Registry Number [1405-10-3]) Neomycin is an antibiotic complex of the aminoglycosides group, extracted from Strepto- 311.1 Suggested Reading myces fradiae. It is composed of neomycin A (neamin) and an isomer neobiosamin, either neo- De Groot AC (1994) Occupational contact allergy mycin B (framycetin or Soframycin®) or neomy- to alpha-naphthyl glycidyl ether. Contact Der- cin C. Its use has been progressively forbidden in matitis 30:253–254 cosmetics and as an additive for animal feed. Occupational contact dermatitis occurs in workers at animal feed mills, in veterinaries, or in health 312 Naphthol AS workers. Nonoccupational dermatitis mainly con- cerns patients with chronic dermatitis, leg ulcers, CI 37505, CI Azoic Coupling Component 2 or chronic otitis. Cross-sensitivity is usual with CAS Registry Number [92-77-3] other aminoglycosides (amikacin, arbekacin, Naphthol AS is a coupling agent in cotton butirosin, dibekacin, gentamicin, isepamicin, dyeing, inducing occupational dermatitis or con- kanamycin, paromomycin, ribostamycin, tact allergy in consumers in contact with cotton- Dictionary of Contact Allergens: Chemical Structures, Sources, and References 135 sisomycin, tobramycin), is rare with netilmicin in patients who start smoking again after skin and streptomycin, but nonexistent with sensitization. spectinomycin. N

NH2 N HO O Neamin HO

H2N H2N O O NH2 314.1 Suggested Reading OH HO Bircher AJ, Howald H, Rufli T (1991) Adverse O skin reactions to nicotine in a transdermal ther- HO O HO apeutic system. Contact Dermatitis NH 25:230–236 2 O OH Neobiosamin Vincenzi C, Tosti A, Cirone M, Guarrera M, H N 2 Cusano F (1993) Allergic contact dermatitis from transdermal nicotine systems. Contact – 313.1 Suggested Reading Dermatitis 29:104 105

Le Coz CJ (2001) Fiche d’éviction en cas 315 3-Nitro-4- d’hypersensibilité à la néomycine. Ann hydroxyethylaminophenol Dermatol Venereol 128:1359–1360 Mancuso G, Staffa M, Errani A et al (1990) Occu- 4-[(2-Hydroxyethyl)amino]-3-nitrophenol pational dermatitis in animal feed mill workers. CAS Registry Number [65235-31-6] Contact Dermatitis 22:37–41 This dye belongs to the aminophenol class and Rebandel P, Rudzki E (1986) Occupational con- is used as a hair colorant, particularly in semiper- tact sensitivity in oculists. Contact Dermatitis manent hair dye preparations. 15:92

OH 314 Nicotine

CAS Registry Number [55-11-5]

Nicotine is an alkaloid found in tobacco and is NO2 responsible for its pharmacological effects and addiction. Contact dermatitis from nicotine, con- NH sidered as rare, has been more frequent since its use in transdermal systems. Irritant dermatitis is mainly encountered, as contact urticaria seems to HO be rare. Allergic contact dermatitis, sometimes generalized, has been reported, with positive patch testing to nicotine base (10% ethanol or petrolatum). No consequences have been reported 136 J.-P. Lepoittevin and C. J. Le Coz

315.1 Suggested Reading 317 Nitrofurazone

Le Coz CJ, Kühne S, Engel F (2003) Hair dye Nitrofural, Nitrozone, Aldomycin allergy due to 3-nitro- p-hydroxyethyl- CAS Registry Numbers [59-87-0], [60051-85-6], aminophenol. Contact Dermatitis 49:103 and [8027-71-2] Søsted H, Rustemeyer T, Gonçalo L et al (2013) Nitrofurazone is an antibacterial agent used in Contact allergy to common ingredients in hair animal feeds. Occupational dermatitis was dyes. Contact Dermatitis 69:32–39 reported in cattle breeders or farmers.

H 316 2-Nitro-4-Phenylenediamine O O2N N N NH2 o-Nitro-p-phenylenediamine, ONPD, CI 76070 CAS Registry Number [5307-14-2] ONPD is a hair dye and a sensitizer in hair- O dressers and consumers who are generally sensi- tive to PPD too. 317.1 Suggested Reading

NH2 Condé-Salazar L, Guimaraens D, Gonzalez MA NO 2 et al (1995) Occupational allergic contact der- matitis from nitrofurazone. Contact Dermatitis 32:307–308 Vilaplana J, Grimalt F, Romaguera C (1990) Con- tact dermatitis from furaltadone in animal feed. NH2 Contact Dermatitis 22:232–233 316.1 Suggested Reading

Frosch PJ, Burrows D, Camarasa JG et al (1993) 318 Nitroglycerin Allergic reactions to a hairdresser’s series: results from 9 European centres. Contact Der- Glyceryl Trinitrate, Glycerol Trinitrate matitis 28:180–183 CAS Registry Number [55-63-0] Guerra L, Tosti A, Bardazzi F et al (1992) Contact Nitroglycerin is an explosive agent contained dermatitis in hairdressers: the Italian experi- in dynamite and an antianginal and vasodilator ence. Gruppo Italiano Ricerca Dermatiti da treatment available in systemic and topical Contatto e Ambientali. Contact Dermatitis forms. It is a well-known irritant agent in dyna- 26:101–107 mite manufacture. It can also cause allergic reac- Søsted H, Rustemeyer T, Gonçalo L et al (2013) tions in employees of explosives manufacturers Contact allergy to common ingredients in hair and in the pharmaceutical industry. Transdermal dyes. Contact Dermatitis 69:32–39 systems are the main source of iatrogenic sensiti- Van der Walle HB, Brunsveld VM (1994) Derma- zation. Nitroglycerin can cross-react with iso- titis in hairdressers (I). The experience of the sorbide dinitrate. past 4 years. Contact Dermatitis 30:217–220 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 137

O O- O OH N+ N+ n -O O O O

O O- + N 319.1 Suggested Reading O Dooms-Goossens A, Deveylder H, de Alam AG et al (1989) Contact sensitivity to nonoxynols 318.1 Suggested Reading as a cause of intolerance to antiseptic prepara- tions. J Am Acad Dermatol 21:723–727 Aquilina S, Felice H, Boffa MJ (2002) Allergic Meding B (1985) Occupational contact dermatitis reactions to glyceryl trinitrate and isosorbide from nonylphenolpolyglycolether. Contact dinitrate demonstrating cross-sensitivity. Clin Dermatitis 13:122–123 Exp Dermatol 27:700–702 Nethercott JR, Lawrence MJ (1984) Allergic con- Kanerva L, Laine R, Jolanki R et al (1991) Occu- tact dermatitis due to nonylphenol ethoxylate pational allergic contact dermatitis caused by (nonoxynol-6). Contact Dermatitis nitroglycerin. Contact Dermatitis 24:356–362 10:235–239 Wilkinson SM, Beck MH, August PJ (1995) Allergic contact dermatitis from nonoxynol- 319 Nonoxynols 12 in a polish. Contact Dermatitis 33:128–129

Nonylphenol Ethoxylates, PEG-(n) Nonyl Phenyl Ether, Polyoxyethylene (n) Nonyl Phenyl Ether 320 Octocrylene CAS Registry Number [26027-38-3] and more than 25 other numbers Octocrylene Their general formula is CAS Registry Number [6197-30-4] fi C9H19C6H4(OCH2CH2) nOH. Each nonoxynol Octocrylene is an anti-UVB lter used in cos- is characterized by the number (n) of ethylene metics that may induce photoallergic contact oxide units repeated in the chain, for example, dermatitis. nonoxynol-9 and nonoxynol-14. They are present in detergents, liquid soaps, emulsifiers for creams, O fabric softeners, photographic paper additives, NC hair dyes, lubricating oils, spermicides, and anti- O infective agents. They are irritants and sensitizers. Nonoxynol-6 was reported as a sensitizing agent in an industrial hand cleanser and in a crack- indicating fluid in the metal industry. Nonoxynol-9 is the most commonly used, as a preservative in topical antiseptics or in spermi- cides, acting as an iodophor in PVP-iodine solu- 320.1 Suggested Reading tions. Nonoxynol-10 was reported as a UVB-photosensitizer. Nonoxynol-12 caused con- Carrotte-Lefebvre I, Bonnevalle A, Segard M et al tact dermatitis in a domestic cleaner who used a (2003) Contact allergy to octocrylene. Contact polish containing it. Dermatitis 48:46–47 138 J.-P. Lepoittevin and C. J. Le Coz

De Groot A, Roberts DW (2014) Contact and O photocontact allergy to octocrylene: a review. Contact Dermatitis 70:193–204 N

S 321 Octyl Gallate

CAS Registry Number [1034-01-1] Octyl gallate, a gallate ester (E 311), is an 322.1 Suggested Reading antioxidant added to food and cosmetics to pre- vent oxidation of unsaturated fatty acids. Cases Ghazavi MK, Johnston GA (2011) An outbreak of were sparsely reported in food industry or from occupational allergic contact dermatitis caused lipsticks. Patch tests are frequently irritant. by 2-N-octyl-4-isothiazolin-3-one among workers in an adhesive factory. Contact Der- – OH matitis 64:114 115 Oleaga JM, Aguirre A, Landa N et al (1992) HO OH Allergic contact dermatitis from Kathon 893. Contact Dermatitis 27:345–346 Young HS, Ferguson JEF, Beck MH (2004) Con- tact dermatitis from 2-n-octyl-4-isothiazoline- 3-one in a PhD student. Contact Dermatitis O O 50:47–48

321.1 Suggested Reading 323 Olaquindox

De Groot AC, Gerkens F (1990) Occupational N-(2-Hydroxyethyl)-3-methyl-2-quinoxalinecar- airborne contact dermatitis from octyl gallate. boxamide-1,4-dioxide Contact Dermatitis 23:184–186 CAS Registry Number [23696-28-8] Giordano-Labadie F, Schwarze HP, Bazex J Olaquindox is an antibacterial agent derivative (2000) Allergic contact dermatitis from octyl of quinoxaline, used as a growth promoter of pigs. gallate in lipstick. Contact Dermatitis 42:51 It can be found in Bayo-N-Ox® and Proquindox® and numerous other pig feeds. It is a photosensi- tizer that forms reactive photoproducts on light 322 2-N-Octyl-4-isothiazolin-3-one exposure. It can induce photoallergic contact der- matitis and persistent light reactions. Kathon® LM, Kathon® 4200, Kathon® 893, Pancil, Skane M-8 O O CAS Registry Number [26530-20-1] This isothiazolinone, contained in relatively N OH N few products compared to other isothiazolinones, is used in cleaning and polishing agents, latex H paints, stains, adhesives, wood and leather pre- N servatives, metalworking fluids (cutting oils), and plastic manufacture. O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 139

323.1 Suggested Reading Alwan W, Banerjee P, White IR (2014) Occupa- tional contact dermatitis caused by omeprazole Belhadjali H, Marguery MC, Journe F et al (2002) in a veterinary medicament. Contact Dermati- Allergic and photoallergic contact dermatitis to tis 71:376 Olaquindox in a pig breeder with prolonged Ghatan PH, Marcusson-Stahl, Matura M et al photosensitivity. Photodermatol Photo- (2014) Sensitization to omeprazole in the occu- immunol Photomed 18:52–53 pational setting. Contact Dermatitis Kumar A, Freeman S (1996) Photoallergic contact 71:371–375 dermatitis in a pig farmer caused by olaquindox. Contact Dermatitis 35:249–250 Schauder S, Schröder W, Geier J (1996) 325 Oxacillin Olaquindox-induced airborne photoallergic contact dermatitis followed by transient or per- CAS Registry Number [66-79-5] sistent light reactions in 15 pig breeders. Con- Oxacillin Sodium Salt Monohydrate: CAS tact Dermatitis 35:344–354 Registry Number [7240-38-2] Oxacillin is a semisynthetic penicillin of the group M. It is closely related to cloxacillin. 324 Omeprazole

N-(2-Hydroxyethyl)-3-methyl-2-quinoxalinecar- O H H boxamide-1,4-dioxide N S CAS Registry Number [73590-58-6] H Omeprazole is a proton-pump inhibitor used in N fl N the treatment of gastroesophageal re ux disease O and has been associated with occupational contact O dermatitis in pharmaceutical workers. Omepra- COOH zole is also used as a veterinary product and has been responsible of occupational contact dermati- tis in race horse breeder. 325.1 Suggested Reading

Bruevich TS, Zakharov GA (1978) Semi- synthetic penicillins, ampicillin and oxacillin and their role in development of occupational allergic dermatoses. Vestn Dermatol Venerol 3:74–78

326 7-Oxodehydroabietic Acid 324.1 Suggested Reading CAS Registry Number [18684-55-4] Al-Falah K, Schachter J, Sasseville D (2014) 7-Oxodehydroabietic acid is an auto-oxidation Occupational allergic contact dermatitis product of dehydroabietic acid and an allergen caused by omeprazole in a horse breeder. Con- contained in colophony. tact Dermatitis 71:377–378 140 J.-P. Lepoittevin and C. J. Le Coz

328 Pantothenol

2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dime- thylbutanamide, Pantothenylol, N-Pantoyl-3-pro- panolamine, Panthenol, Pantothenyl Alcohol CAS Registry Number [81-13-0] Pan(to)thenol is the alcohol corresponding to O pantothenic acid, of the vitamin B5 group. It is OH used as a food additive and in skin and hair prod- O ucts as a conditioning agent. Contact dermatitis and urticaria have been reported.

326.1 Suggested Reading H OH

N Bergh M, Menné T, Karlberg AT (1994) Colo- HO OH phony in paper-based surgical clothing. Con- tact Dermatitis 31:332–333 O

327 Oxprenolol 328.1 Suggested Reading

CAS Registry Number [6452-71-7] Schalock PC, Storrs FJ, Morrison L (2000) Con- The beta-blocker oxprenolol induced contact tact urticaria from panthenol in hair condi- dermatitis in a worker at a pharmaceutical plant, in tioner. Contact Dermatitis 43:223 a division for drug synthesis. Epichlorhydrin was Stables GI, Wilkinson SM (1998) Allergic contact also used for the production of drugs propranolol dermatitis due to panthenol. Contact Dermati- – and oxprenolol. tis 38:236 237

OH H 329 Parabens (Parahydroxybenzoic O N Acid Esters)

Methylparaben, E218, E219 (Sodium Salt) O CAS Registry Number [99-76-3], E219 (Sodium Salt), CAS Registry Number [5026-62-0] Ethylparaben, E214, E215 (Sodium Salt) 327.1 Suggested Reading CAS Registry Number [120-47-8], E215 (Sodium Salt), CAS Registry Number [35285- Rebandel P, Rudzki E (1990) Dermatitis caused 68-8] by epichlorhydrin, oxprenolol hydrochloride Propylparaben, E216, E217 (Sodium Salt) and propranolol hydrochloride. Contact Der- CAS Registry Number [94-13-3], E217 matitis 23:199 (Sodium Salt), CAS Registry Number [35285- 69-9] Isopropylparaben CAS Registry Number [4191-73-5] Dictionary of Contact Allergens: Chemical Structures, Sources, and References 141

Butylparaben 329.1 Suggested Reading CAS Registry Number [94-26-8] Isobutylparaben Le Coz CJ (2004) Fiche d’éviction en cas CAS Registry Number [4247-02-3] d’hypersensibilité aux esters de l’acide para- Phenylparaben hydroxybenzoïque (parahydroxybenzoates ou CAS Registry Number [17696-62-7] parabens). Ann Dermatol Venereol Benzylparaben 131:309–310 CAS Registry Number [94-18-8] Phenoxyethylparaben CAS Registry Number [55468-88-7] 330 p-Phenylenediamine Parabens are esters formed by p- hydroxybenzoic acid and an alcohol. They are PPD, Paraphenylenediamine, 4-Phenylenediamine largely used as biocides in cosmetics and toilet- CAS Registry Number [106-50-3] ries, medicaments, or food. They have synergistic PPD is a colorless compound oxidized by power with other biocides. Parabens can induce hydrogen peroxide in the presence of ammonia. allergic contact dermatitis, mainly in chronic der- It is then polymerized to a color by a coupling matitis and wounded skin. agent. Although a well-known allergen in hair dyes, PPD can be found as a cause of contact

OH OH OH OH OH OH OH

O OH OOOOOOOO OOOO

Methyl-

Ethyl- Isopropyl- Isobutyl- P-Hydroxybenzoic acid Propyl- Butyl-

OH OH OH OH OH

O O OO OO O O O O

O

Phenyl- Benzyl-

Hexyl- Phenoxyethyl-paraben Isodecyl- 142 J.-P. Lepoittevin and C. J. Le Coz dermatitis in chin rest stains or in milk testers. It is CAS Registry Numbers [4685-14-7] and also a marker of group sensitivity to para-amino [116047-10-0] (CAS Registry Number [1910- compounds such as benzocaine, some azo dyes, 42-5], CAS Registry Number [2074-50-2]) and some previous antibacterial sulphonamides. Paraquat is a quaternary ammonium com- pound with herbicide properties, as diquat. It is ® ® NH2 contained in Cekuquat or Dipril . It can cause contact and phototoxic contact dermatitis, acne, and leukoderma mainly in agricultural workers.

+ N

NH2

+ 330.1 Suggested Reading N

Bork K (1993) Allergic contact dermatitis on a violinist’s neck from para-phenylenediamine in 331.1 Suggested Reading a chin rest stain. Contact Dermatitis 28:250–251 Cordoba S, Sanz-Sanchez T, Hernandez-Nunez A Vilaplana J, Azon A, Romaguera C et al (1993) et al (2008) Occupational contact dermatitis Phototoxic contact dermatitis with toxic hepa- from P-phenylenediamine in a furrier. J titis due to the percutaneous absorption of EADV 22:773 paraquat. Contact Dermatitis 29:163–164 Guerra L, Tosti A, Bardazzi F et al (1992) Contact dermatitis in hairdressers: the Italian experi- ence. Gruppo Italiano Ricerca Dermatiti da 332 Parathion Contatto e Ambientali. Contact Dermatitis 26:101–107 Parathion-ethyl: Parathion, Ethylparathion, Le Coz CJ, Lefebvre C, Keller F et al (2000) Corothion, Dantion, Folidol Allergic contact dermatitis caused by skin paint- CAS Registry Number [56-38-2] ing (pseudotattooing) with black henna, a mix- Parathion-methyl: Methylparathion, Matafos, ture of henna and p-phenylenediamine and its Paratox, Folidol M derivatives. Arch Dermatol 136:1515–1517 CAS Registry Number [298-00-0] Rebandel P, Rudzki E (1995) Occupational One case was reported of a bullous contact allergy to p-phenylenediamine in milk testers. dermatitis due to ethylparathion. A case of sensi- Contact Dermatitis 33:138 tization to methyl-parathion was described in a Søsted H, Rustemeyer T, Gonçalo L et al (2013) female agricultural worker with multiple Contact allergy to common ingredients in hair sensitization. dyes. Contact Dermatitis 69:32–39

NO2 S NO2 S P 331 Paraquat (Dichloride, P O O O O O Methosulfate) O

Methyl-Parathion Ethyl-Parathion 1-1-Dimethyl-4,4-bipyridinium Salt Dictionary of Contact Allergens: Chemical Structures, Sources, and References 143

332.1 Suggested Reading 334 Penicillins

Jung HD, Holzegel K (1988) Akute Toxisch- CAS Registry Number [1406-05-9] for Penicillin bullöse Kontaktdermatitis durch den Penicillins can induce contact dermatitis, con- Phosphorsäurester Parathionethyl im Follidel- tact urticaria, and systemic and sometimes severe Öl. Aktuel Dermatol 14:19–31 reactions. Occupational sensitivity to penicillins concerns health workers, workers in the pharma- ceutical industry, and veterinaries, since these 333 Parthenolide antibiotics are used by veterinarians and cattle breeders as medications and animal feed antibi- CAS Registry Number [20554-84-1] otic. All penicillins contain the Parthenolide is a sesquiterpene lactone found 6-aminopenicillanic acid moiety. Penicillins in Asteraceae-Compositae such as feverfew of G, V, A, and M groups are characterized by a

(Tanacetum parthenium Schultz-Bip.) or congress specificC7 side chain. Cross-reactivity is possible grass (Parthenium hysterophorus L.). between several penicillins, but is not systematic since both immediate- and delayed-type sensitiv- ity can implicate the 6-aminopenicillanic acid moiety or be specific to the 7-side chain.

H O R O H H N O S

O N 333.1 Suggested Reading O

Hausen BM, Osmundsen PE (1983) Contact OH allergy to parthenolide in Tanacetum O parthenium (L.) Schultz-Bip. (feverfew, Asteraceae) and cross-reactions to related ses- quiterpene lactone containing Compositae spe- 334.1 Suggested Reading cies. Acta Derm Venereol (Stockh) 63:308–314 Guerra L, Venturo N, Tardio M, Tosti A (1995) Lamminpää A, Estlander T, Jolanki R et al (1996) Airborne contact dermatitis from animal feed Occupational allergic contact dermatitis antibiotics. Contact Dermatitis 32:61–62 caused by decorative plants. Contact Dermati- Rudzki E, Rebandel P, Grzywa Z (1989) Patch tis 34:330–335 tests with occupational contactants in nurses, Paulsen E, Andersen KE, Hausen BM (1993) doctors and dentists. Contact Dermatitis Compositae dermatitis in a Danish dermatol- 20:247–250 ogy department in one year (I). Results of routine patch testing with the sesquiterpene lactone mix supplemented with aimed patch 335 Pentachloronitrobenzene testing with extracts and sesquiterpene lac- tones of Compositae plants. Contact Dermati- Quintozene, PCNB, Brassicol, Terrachlor® tis 29:6–10 CAS Registry Number [82-68-8] 144 J.-P. Lepoittevin and C. J. Le Coz

Pentachloronitrobenzene is a pesticide and a 337 Phenoxyethanol fungicide. Sensitization can occur in farmers or in chemical plants. 2-Phenoxyethanol CAS Registry Numbers [122-99-6], [37220-

NO2 49-8], and [56257-90-0] Phenoxyethanol is an aromatic ether alcohol CI CI used mainly as a preservative, mostly with methyldibromoglutaronitrile (in Euxyl® K 400) or with parabens. Sensitization to this molecule CI CI is very rare. CI O OH 335.1 Suggested Reading

O’Malley M, Rodriguez P, Maibach HI (1995) Pesticide patch testing: California nursery 337.1 Suggested Reading workers and controls. Contact Dermatitis 32:61–62 Gallo R, Marro I, Sorbara S (2005) Contact Sharma VK, Kaur S (1990) Contact sensitization allergy from phenoxyethanol on Fitostimoline by pesticides in farmers. Contact Dermatitis gauzes. Contact Dermatitis 53:23 23:77–80 Vigan M, Brechat N, Girardin P et al (1996) Un nouvel allergène: le dibromodicyanobutane. 336 Pentadecylcatechol Etude sur 310 patients de janvier à décembre 1994. Ann Dermatol Venereol 123:322–324 3-Pentadecylcatechol, Hydrourushiol, Tetrahy- drourushiol 338 Phenyl Glycidyl Ether CAS Registry Number [492-89-7] Pentadecylcatechol belongs to the urushiols CAS Registry Numbers [122-60-1] and [66527- and is the main allergen of the Anacardiaceae 93-3] poison ivy (Toxicodendron radicans) and of Poi- This monoglycidyl derivative is a reactive dil- son oak (Toxicodendron diversiloba, Rhus uent in epoxy resins bisphenol A type. It is a diversiloba). component of epoxy paints, epoxy glues, and epoxy resins. Sensitization has been observed in OH many professions, such as in construction OH workers, marble workers, ceramic workers, and shoemakers.

O 336.1 Suggested Reading O

Epstein WL (1994) Occupational poison ivy and oak dermatitis. Dermatol Clin 12:511–516 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 145

338.1 Suggested Reading Svedman C, Isaksson M, Zimerson E et al (2004) Occupational contact dermatitis from a grease. Aalto-Korte K, Pesonen M, Suuronen K (2015) Dermatitis 15:41–44 Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sen- sitizing products and diagnosis. Contact Der- 340 Phenyl-beta-naphthylamine matitis 73:336–342 Angelini G, Rigano L, Foti C et al (1996) Occu- N-Phenyl-2-naphthylamine, Neozone pational sensitization to epoxy resin and reac- CAS Registry Numbers [135-88-6], [52907- tive diluents in marble workers. Contact 17-2], and [84420-28-0] Dermatitis 35:11–16 Phenyl-beta-naphthylamine is an amine com- Condé-Salazar L, Gonzalez de Domingo MA, pound. Sensitization was reported in patients with Guimaraens D (1994) Sensitization to epoxy hypersensitivity from rubber. resin systems in special flooring workers. Con- tact Dermatitis 31:157–160 H N Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. Con- tact Dermatitis 34:17–22 Tarvainen K (1995) Analysis of patients with allergic patch test reactions to a plastic and glues series. Contact Dermatitis 32:346–351 340.1 Suggested Reading

Condé-Salazar L, Guimaraens D, Romero LVet al 339 Phenyl-Alpha-Naphthylamine (1987) Unusual allergic contact dermatitis to aromatic amines. Contact Dermatitis 17:42–44 Neozone A, CI 44050 Condé-Salazar L, Del-Rio E, Guimaraens D et al CAS Registry Number [90-30-2] (1993) Type IV allergy to rubber additives: a Phenyl-alpha-naphthylamine is contained in 10-year study of 686 cases. J Am Acad some rubbers and oils as an antioxidant of the Dermatol 29:176–180 amine group. It is closely related to phenyl-beta- Kiec-Swierczynska M (1995) Occupational sen- naphthylamine and to di-beta-naphthyl- p- sitivity to rubber. Contact Dermatitis phenylenediamine but without cross-reactivity. 32:171–172

341 Phenylephrine (Hydrochloride)

HN CAS Registry Number [59-42-7] Phenylephrine Hydrochloride: CAS Registry Number [61-76-7] Phenylephrine hydrochloride is an alpha- adrenergic agonist, used as a mydriatic and decon- gestant in eyedrops.

339.1 Suggested Reading

Carmichael AJ, Foulds IS (1990) Isolated naph- thylamine allergy to phenyl-alpha-naphthyl- amine. Contact Dermatitis 22:298–299 146 J.-P. Lepoittevin and C. J. Le Coz

OH poplar bud resin in a tree surgeon. Contact H Dermatitis 27:127–128 HO N (•HCI)

343 Phthalic Anhydride

CAS Registry Numbers [85-44-9] and 341.1 Suggested Reading [39363-63-8] Phthalic anhydride is used in the manufacture Borch JE, Elmquist JS, Bindslev-Jensen et al of unsaturated polyesters and as a curing agent for (2005) Phenylephrine and acute periorbital epoxy resins. When used as a pigment, it can be dermatitis. Contact Dermatitis 53:298–299 responsible for sensitization in ceramic workers. Narayan S, Prais L, Foulds IS (2002) Allergic Phthalic anhydride per se is not responsible for the contact dermatitis caused by phenylephrine sensitization to the resin used in nail varnishes eyedrops. Am J Contact Dermat 13:208–209 phthalic anhydride/trimellitic anhydride/glycols copolymer, CAS Registry Number [85-44-9].

342 Phenylethyl Caffeate o

Caffeic Acid Phenethyl Ester, Capee o CAS Registry Number [104594-70-9] Capee is one of the allergens of propolis (bee glue). It is also contained in poplar bud secretions. o

OH 343.1 Suggested Reading HO Seidenari S, Danese P, di Nardo A et al (1990) O Contact sensitization among ceramics workers. Contact Dermatitis 22:45–49 O Tarvainen K, Jolanki R, Estlander T et al (1995) Immunologic contact urticaria due to airborne methylhexahydrophthalic and methyltetrahy- 342.1 Suggested Reading drophthalic anhydrides. Contact Dermatitis 32:204–209 Lamminpää A, Estlander T, Jolanki R et al (1996) Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- 344 Picric Acid tis 34:330–335 Langan SM, English JS (2007) Occupational con- CI 10305 tact dermatitis from propolis in a dental tech- CAS Registry Number [88-89-1] nician. Contact Dermatitis 56:43 Contact dermatitis occurred primarily in the Oliwiecki S, Beck MH, Hausen BM (1992) Occu- explosives industry. pational contact dermatitis from caffeates in Dictionary of Contact Allergens: Chemical Structures, Sources, and References 147

OH 346 Beta-pinene

O N 2 NO2 Nopinene, Terebenthene CAS Registry Number [127-91-3] Beta-pinene is a component of turpentine. Concentrations vary with the source and seem

NO2 higher in European (Portuguese) than in Asian (Indonesian) turpentine.

344.1 Suggested Reading

Aguirre A, Sanz de Galdeano C, Oleaga JM et al (1993) Allergic contact dermatitis from picric acid. Contact Dermatitis 28:291 Hausen BM (1994) Letter to the editor. Picric acid. Contact Dermatitis 30:59 346.1 Suggested Reading

345 Alpha-Pinene Lear JT, Heagerty AHM, Tan BB et al (1996) Transient re-emergence of oil turpentine CAS Registry Numbers [80-56-8] and allergy in the pottery industry. Contact Derma- [2437-95-8] titis 35:169–172 Alpha-pinene is the major constituent of tur- pentine (about 80%). It exists in levogyre form in European turpentine and in dextrogyre form in 347 Piperazine turpentine found in North Americans. Sensitiza- tion occurs mainly in painters, polishers, and var- Diethylenediamine nishers and in those in the perfume and in the CAS Registry Number [110-85-0] ceramics industry. Piperazine is contained in pyrazinobutazone, an equimolar salt of piperazine and phenylbuta- zone. Among occupational cases, most were reported in the pharmaceutical industry or labora- tory workers, in nurses, and in veterinarians.

H

N

345.1 Suggested Reading N Lear JT, Heagerty AHM, Tan BB et al (1996) Transient reemergence of oil turpentine allergy H in the pottery industry. Contact Dermatitis 35:169–172 347.1 Suggested Reading Moura C, Dias M, Vale T (1994) Contact derma- titis in painters, polishers and varnishers. Con- Dorado Bris JM, Montanes Aragues M, Sols Can- tact Dermatitis 31:51–53 dela M et al (1992) Contact sensitivity to 148 J.-P. Lepoittevin and C. J. Le Coz

pyrazinobutazone (Carudol®) with positive 349 Pivampicillin oral provocation test. Contact Dermatitis 26:355–356 CAS Registry Number [33817-20-8] Rudzki E, Rebandel P, Grzywa Z et al (1982) Pivampicillin Hydrochloride Occupational dermatitis in veterinarians. Con- CAS Registry Number [26309-95-5] tact Dermatitis 8:72–73 Pivampicillin is a prodrug of ampicillin. It caused sensitization in 56 workers at a penicillin factory. Pivampicillin and pivmecillinam were 348 Piroxicam responsible for contact dermatitis in pharmaceuti- cal production workers. Ampicillin, mecillinam or CAS Registry Number [36332-90-4] amdinocillin, and penicillin V and penicillin G This nonsteroidal anti-inflammatory drug were also implicated in cross-reactions. belongs to the oxicam class. It induces photo- allergic contact dermatitis rather than contact O allergy. Systemic photosensitivity is frequent, in patients previously sensitized to . N S Thiosalicylic acid, the nonmercurial moiety of O NH H thiomersal, is a marker of photoallergy to 2 N O piroxicam. Reactions are expected with piroxicam O O β-cyclodextrin, but cross-sensitivity is generally O not observed to tenoxicam or meloxicam (per- sonal observations). 349.1 Suggested Reading

OH O Moller NE, von Würden K (1992) Hypersensitiv- ity to semisynthetic penicillins and cross- N N reactivity with penicillin. Contact Dermatitis – N H 26:351 352 S Moller NE, Nielsen B, von Würden K (1990) O O Changes in penicillin contamination and allergy in factory workers. Contact Dermatitis 22:106–107 348.1 Suggested Reading

Arévalo A, Blancas R, Ancona A (1995) Occupa- 350 Polyaminopropyl Biguanide tional contact dermatitis from piroxicam. Am J Contact Dermat 6:113–114 CAS Registry Number [133029-32-0] De la Cuadra J, Pujol C, Aliaga A (1989) Clinical PAPB evidence of cross-sensitivity between Polyaminopropyl biguanide is broad- thiosalicylic acid, a contact allergen, and spectrum, fast-acting bactericide that is widely piroxicam, a photoallergen. Contact Dermatitis used as preservative for cosmetics such as make- 21:349–351 up removers, toners, facial cleanser, and wet wipes. It is permitted at concentration of 0.3% according to Annex VI of the European Cosmetics Directive 76/768/EEC. Cases of contact urticarial to this chemical have been reported. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 149

351.1 Suggested Reading

Jiaravuthisan MM, DeKoven JG (2008) Contact dermatitis to polymyxin B. Contact Dermatitis 59:314–316 350.1 Suggested Reading 352 Potassium Metabisulfite Creytens K, Goossens A, Faber M et al (2014) Contact urticarial syndrome caused by poly- Sodium Pyrosulfite, Disodium Disulfite, E224 aminopropyl biguanide in wipes for intimate CAS Registry Number [16731-55-8] – hygiene. Contact Dermatitis 71:307 309 Potassium metabisulfite is an antioxidant used as an antifermentative agent in breweries and win- eries, as a preservative of fruits and vegetables, 351 Polymyxin B (Sulfate) and to bleach straw. Reactions to both sodium and potassium metabisulfite are expected. CAS Registry Number [1404-26-8] (CAS Regis- try Number [1405-20-5]) OO Polymyxin, CAS Registry Number [1406-11- S S 7], is a polypeptidic antibiotic complex (Poly- - - myxin A to E) produced by Bacillus polymyxa. OOO Polymyxin E is known as Colistin. Active against K+ K+ Gram-negative bacteria, Polymyxin B is a mixture of Polymyxin B1 and B2. Sensitization occurs by topical, ophthalmic, and otic preparations. 352.1 Suggested Reading Cosensitization is frequent with other topical anti- biotics like neomycin or bacitracin. Stingeni L, Bianchi L, Lisi P (2009) Occupational airborne allergic contact dermatitis from potas- sium metabisulfite. Contact Dermatitis 60:52–53

O O H2N NH HN O

OH O NH HN NH2 O O H H N N N N HN O H H H SO O O 2 4 NH HN O NH2 NH2 O NH2 HO 150 J.-P. Lepoittevin and C. J. Le Coz

353 Povidone-Iodine 354.1 Suggested Reading

Polyvinylpyrrolidone-Iodine, PVP-Iodine Le Coz CJ, Cribier BJ, Heid E (1996) Patch test- CAS Registry Number [25655-41-8] ing in suspected allergic contact dermatitis due Povidone-iodine is iodophor, used as a topical to Emla® cream in haemodialyzed patients. antiseptic. A 10% povidone-iodine solution con- Contact Dermatitis 35:316–317 tains 1% available iodine, but free iodine is at Garcia F (2007) Contact dermatitis from prilocaine 0.1% concentration. Skin exposure causes irritant with cross-sensitivity to pramocaine and rather than allergic contact dermatitis. In such a bupivacaine. Contact Dermatitis 56:120–121 situation, however, iodine seems to be the true hapten. 355 Primin

CAS Registry Number [15121-94-5] n Primin is the major allergen of Primula N O obconica Hance (Primulaceae family). Allergic contact dermatitis is mainly occupational, occur- ring in florists and horticulturists.

O 353.1 Suggested Reading O Amschler K, Fuchs T, Geier J et al (2017) In search for a better patch test concentration for povidone-iodine. Contact Dermatitis 77:346–347 O Lachapelle JM (2005) Allergic contact dermatitis from povidone-iodine: a reevaluation study. 355.1 Suggested Reading Contact Dermatitis 52:9–10 Tosti A, Vincenzi C, Bardazzi F, Mariani R (1990) Christensen LP, Larsen E (2000) Direct emission Allergic contact dermatitis due to povidone- of the allergen primin from intact Primula – iodine. Contact Dermatitis 23:197 198 obconica plants. Contact Dermatitis 42:149–153 Lamminpää A, Estlander T, Jolanki R et al (1996) 354 Prilocaine (Hydrochloride) Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- CAS Registry Number [25655-41-8] (CAS Reg- tis 34:330–335 istry Number [1786-81-8]) Prilocaine in a local anesthetic of the amide group. It can induce allergic contact dermatitis, 356 Pristinamycin particularly from EMLA® cream. Pristinamycin H CAS Registry Number [270076-60-3] N Pristinamycin IA (Streptogramin B, N H Mikamycin IA, Ostreogrycin B, Vernamycin O Balpha) Dictionary of Contact Allergens: Chemical Structures, Sources, and References 151

CAS Registry Number [3131-03-1] 356.1 Suggested Reading Pristinamycin IIA (Mikamycin A,

Ostreogrycin A, Pristinamycin IIA, Barbaud A, Trechot P, Weber-Muller F et al Staphylomycin M1, Streptogramin A, (2004) Drug skin tests in cutaneous adverse Vernamycin A, Virginiamycin M1) drug reactions to pristinamycin: 29 cases with CAS Registry Number [21411-53-0] a study of cross-reactions between syn- Pristinamycin is a systemic antibiotic of the ergistins. Contact Dermatitis 50:22–26 synergistins/streptogramins class, composed of two subunits: pristinamycin IA and pristinamycin IIA. It induces several types of drug reactions such 357 Procaine (Hydrochloride) as maculopapular exanthema, systemic dermati- tis, or acute generalized exanthematous 2-Diethylaminoethyl 4-Aminobenzoate, pustulosis. Some patients have been previously Novocaine® skin-sensitized by virginiamycin (see below). CAS Registry Number [59-46-1] Cross-reactivity is expected to virginiamycin Procaine Hydrochloride CAS [11006-76-1] and to the associated CAS Registry Number [51-05-8] dalfopristin (CAS [112362-50-2]) and Procaine is a local anesthetic with para-amino quinupristin (CAS [120138-50-3]). function. Sensitization mainly concerns the med- ical, dental, and veterinary professions.

OH N O O HN H N O N N N O O O O O (.HCI) H N N N H2N O O O 357.1 Suggested Reading Pristinamycin IA Berova N, Stranky L, Krasteva M (1990) Studies HN on contact dermatitis in stomatological staff. – OH Dermatol Monatschr 176:15 18 O Rudzki E, Rebandel P, Grzywa Z et al (1982) Occupational dermatitis in veterinarians. Con- O tact Dermatitis 8:72–73 O N O

N O 358 Propacetamol

4-Acetamidophenyl N,N-Diethylglycinate O Hydrochloride Pristinamycin IIA CAS Registry Number [66532-85-2] Propacetamol is a prodrug of paracetamol (acetaminophen) used for intravenous administra- tion. It results from the combination of paraceta- mol and diethylglycine. It caused contact (hand and airborne) dermatitis in nurses and acute 152 J.-P. Lepoittevin and C. J. Le Coz systemic dermatitis (pompholyx and nummular dermatitis, generalized eczema, urticaria-like eruption) in nurses who had become sick and received intravenous propacetamol. Allergenic properties are due to the N,N-diethylglycine moi- O H ety, and not to the paracetamol moiety. Pro- OO pacetamol is now substituted by a solution of S ® paracetamol in (Perfalgan ). O

O 359.1 Suggested Reading N O Nishioka K, Kozuka T, Tashiro M (1970) Agri- cultural miticide (BPPS) dermatitis. Skin Res • HCI 12:15 O’Malley M, Rodriguez P, Maibach HI (1995) Pesticide patch testing: California nursery N workers and controls. Contact Dermatitis H 32:61–62

O 360 Propranolol 358.1 Suggested Reading CAS Registry Number [525-66-6] Barbaud A, Trechot P, Bertrand O et al (1995) Propranolol is a beta-blocking agent that was Occupational allergy to propacetamol. Lancet responsible for the sensitization of workers in 30:902 drug synthesis. In one case, epichlorhydrin was Berl V, Barbaud A, Lepoittevin JP (1998) Mech- used for the production of drugs propranolol and anism of allergic contact dermatitis from pro- oxprenolol. Cross-reactivity is expected between pacetamol: sensitization to activated N,N- beta-blockers. diethylglycine. Contact Dermatitis 38:185–188 Le Coz C, Collet E, Dupouy M (1999) Consé- quences d’une administration systémique de propacétamol (Pro-Dafalgan®) chez les O N infirmières sensibilisées au propacétamol. OH H Ann Dermatol Venereol 126 (Suppl 2):32–33

359 Propargite

Omite® 360.1 Suggested Reading CAS Registry Number [2312-35-8] The pesticide omite principally acts as an irri- Pereira F, Dias M, Pacheco FA (1996) Occupa- tant. Contact dermatitis was reported in 40 of tional contact dermatitis from propranolol, fl 47 agricultural workers using Omite®. hydralazine and bendro umethiazide. Contact Dermatitis 35:303–304 Rebandel P, Rudzki E (1990) Dermatitis caused by epichlorhydrin, oxprenolol hydrochloride Dictionary of Contact Allergens: Chemical Structures, Sources, and References 153

and propranolol hydrochloride. Contact Der- Flexicolor®. Patch tests in aqua are sometimes matitis 23:199 irritant.

HO OH 361 Propyl Gallate

CAS Registry Number [121-79-9] 362.1 Suggested Reading This gallate ester (E 311) is an antioxidant frequently used in the food, cosmetic, and phar- Claverie F, Giordano-Labadie F, Bazex J (1997) maceutical industries to prevent the oxidation of Eczéma de contact au propylène glycol. Ann unsaturated fatty acids into rancid-smelling com- Dermatol Venereol 124:315–317 pounds. It causes cosmetic dermatitis mainly from Connoly M, Buckley DA (2004) Contact derma- lipsticks and induced contact dermatitis in a baker, titis from propylene glycol in ECG electrodes, and in a female confectioner, primarily sensitized complicated by medicament allergy. Contact by her night cream, who fried doughnuts – the Dermatitis 50:42 margarine probably containing gallates. Hernàndez N, Hernàndez Z, Liuti F et al (2017) Intolerance to cosmetics as key to the diagnosis OH in a patient with allergic contact dermatitis HO OH caused by propylene glycol contained in a top- ical medication. Contact Dermatitis 76:246–247 Scheman AJ, Katta R (1997) Photographic aller- gens: an update. Contact Dermatitis 37:130

O O 363 Propylene Oxide 361.1 Suggested Reading CAS Registry Number [75-56-9] Bojs G, Niklasson B, Svensson A (1987) Allergic Propylene oxide is an allergic and irritant contact dermatitis to propyl gallate. Contact agent, used as a solvent and raw material in the Dermatitis 17:294–298 chemical industry, as the starting material and Mahendran R, Quinlan RM, Wilkinson SM intermediate for a broad spectrum of polymers. It (2002) Allergic contact dermatitis from occu- can be used as a dehydrating agent for the prepa- pational propyl gallate exposure. Contact Der- ration of slides in electron microscopy. Occupa- matitis 47:109–125 tional dermatitis was also reported following the use of a skin disinfectant swab.

362 Propylene Glycol O

1,2-Propanediol CAS Registry Number [57-55-6] Propylene glycol is used as a solvent, a vehicle 363.1 Suggested Reading for topical medicaments such as corticosteroids or aciclovir, an emulsifier and humectant in food and Steinkraus V, Hausen BM (1994) Contact allergy cosmetics, and as antifreeze in breweries, in the to propylene oxide. Contact Dermatitis 31:120 manufactures of resins. It was present as an occu- pational sensitizer in the color film developer 154 J.-P. Lepoittevin and C. J. Le Coz

Van Ketel WG (1979) Contact dermatitis from 365 Pyrethroids propylene oxide. Contact Dermatitis 5:191–192 Cypermethrin(e) CAS Registry Number [52315-07-8] Permethrin(e) 364 Pseudoephedrine CAS Registry Number [52645-53-1] Deltamethrin(e) CAS Registry Number [90-82-4] CAS Registry Number [52918-63-5] Pseudoephedrine Hydrochloride: CAS Regis- Bioallethrin(e), Depalethrin(e) try Number [345-78-8] CAS Registry Number [584-79-2] Pseudoephedrine Sulfate: CAS Registry Num- Pyrethroids, also called pyrethrinoids, are neu- ber [7460-12-0] rotoxic synthetic compounds used as insecticides, This sympathomimetic α-adrenergic agonist is with irritant properties. Cypermethrin and found in plants of the genus Ephedra fenvalerate have been reported as causing positive (Ephedraceae) and is systemically used as a allergic patch tests, but only fenvalerate was rele- nasal decongestant. It can induce drug skin reac- vant in an agricultural worker. tions such as acute generalized exanthematic pustulosis or generalized eczema. 365.1 Suggested Reading OH H Flannigan SA, Tucker SB, Key MM et al (1985) N Primary irritant contact dermatitis from syn- thetic pyrethroid insecticide exposure. Arch Toxicol 56:288–294 Lisi P (1992) Sensitization risk of pyrethroid insecticides. Contact Dermatitis 26:349–350 364.1 Suggested Reading

Assier-Bonnet H, Viguier M, Dubertret L et al 366 Pyrethrosin (2002) Severe adverse drug reactions due to pseudoephedrine from over-the-counter medi- CAS Registry Number [28272-18-6] cations. Contact Dermatitis 47:165–182 Pyrethrosin is an allergen of Asteraceae- Fukuda R, Ouchi T, Hirai I et al (2017) Compositae such as Chrysanthemum Non-pigmenting fixed drug eruption with cinerariifolium Vis. mixed features of acute generalized exanthem- atous pustulosis induced by pseudoephedrine: O a case report. Contact Dermatitis 77:123–126 O Padial MA, Alvarez-Ferreira J, Tapia B et al O (2004) Acute generalized exanthematous pustulosis associated with pseudoephedrine. – Br J Dermatol 150:139 142 O

O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 155

CI

O O CI O O O C O Cypermethrin N Bioallethrin

Br O O O Br O O O CI CI Permethrin N Deltamethrin

366.1 Suggested Reading

Mitchell JC, Dupuis G, Towers GHN (1972) Allergic contact dermatitis from pyrethrum N (Chrysanthemum spp.). The roles of pyrethrosin, a sesquiterpene lactone, and of pyrethrin II. Br J Dermatol 86:568–573 367.1 Suggested Reading Paulsen E, Andersen KE, Hausen BM (1993) Compositae dermatitis in a Danish dermatol- Knegt-Junk C, Geursen-Reitsma L, van Joost T ogy department in one year (I). Results of (1993) Allergic contact dermatitis from pyri- routine patch testing with the sesquiterpene dine in Karl Fischer reagent. Contact Dermati- lactone mix supplemented with aimed patch tis 28:252 testing with extracts and sesquiterpene lac- tones of Compositae plants. Contact Dermati- tis 29:6–10 368 Pyrithione

Pyrithione, Omadine 367 Pyridine CAS Registry Number [1121-30-8] Sodium Pyrithione, Sodium Omadine CAS Registry Number [110-86-1] CAS Registry Numbers [1121-30-8] and Pyridine (unsubstituted pyridine) and its deriv- [15922-78-8] ative (substituted pyridines) are widely used in Zinc Pyrithione, Zinc Omadine chemistry. Pyridine is a solvent used for many CAS Registry Number [13463-41-7] and more organic compounds and anhydrous metallic salt than 20 others chemicals. Contained in Karl Fischer reagent, it The sodium salt of N-hydroxy-2- induced contact dermatitis in a laboratory techni- pyridinethiones has germicidal activity against cian. No cross-sensitivity is observed between yeasts and fungi. Sodium omadine is a 40% aque- those different substances. ous solution of sodium pyrithione. It is used in the metallurgical industry as a component of water- based metalworking fluids, of aceto-polyvinyl lat- tices, water-based printer’s ink, a lubricant for synthetic fibers, and antidandruff shampoos. 156 J.-P. Lepoittevin and C. J. Le Coz

Zinc pyrithione is widely used in antidandruff results from 9 European centres. Contact Der- shampoos and is a classic allergen. Concomitant matitis 28:180–183 reactions are expected to both zinc and sodium Guerra L, Tosti A, Bardazzi F et al (1992) Contact pyrithione. dermatitis in hairdressers: the Italian experi- ence. Gruppo Italiano Ricerca Dermatiti da Contatto e Ambientali. Contact Dermatitis 26:101–107

N SH N S 370 PVP − Na+ O O SS Polyvinylpyrrolidone, Polyvidone, Povidone, Zn 2-Pyrrolidinone, 1-Ethenyl-, Homopolymer CAS Registry Number [9003-39-8] N+ N+ − − O O Polyvinylpyrrolidone is widely used as is in cosmetics such as hair care products and in med- ical products. It acts as iodophor in iodine- 368.1 Suggested Reading polyvinylpyrrolidone. PVP is an irritant and has been claimed as the allergen in some cases of Isaksson M (2002) Delayed diagnosis of occupa- dermatitis from iodine-polyvinylpyrrolidone tional contact dermatitis from sodium (although iodine is more likely the hapten). It pyrithione in a metalworking fluid. Contact may cause type I contact urticaria or anaphylaxis. Dermatitis 47:248–249 Le Coz CJ (2001) Allergic contact dermatitis from sodium pyrithione in metalworking fluid. Con- tact Dermatitis 45:58–59 n N O

369 Pyrogallol

1,2,3-Benzenetriol, CI 76515, Pyrogallic Acid CAS Registry Number [87-66-1] 370.1 Suggested Reading Pyrogallol belongs to the phenols group. It is an old photograph developer and a low sensitizer Adachi A, Fukunaga A, Hayashi K, Kunisada M, in hair dyes. Horikawa T (2003) Anaphylaxis to poly- vinylpyrrolidone after vaginal application of povidone-iodine. Contact Dermatitis OH 48:133–136 HO OH Ronnau AC, Wulferink M, Gleichmann E, Unver E, Ruzicka T, Krutmann J, Grewe M (2000) Anaphylaxis to polyvinylpyrrolidone in an analgesic preparation. Br J Dermatol 143:1055–1058 369.1 Suggested Reading

Frosch PJ, Burrows D, Camarasa JG et al (1993) Allergic reactions to a hairdresser’s series: Dictionary of Contact Allergens: Chemical Structures, Sources, and References 157

371 PVP/Eicosene Copolymer

N O Polyvinylpyrrolidone/Eicosene Copolymer CAS Registry Numbers [28211-18-9] and y [77035-98-4] PVP/eicosene copolymer is the polymer of vinylpyrrolidone and of 1-eicosene and one of the 11 PVP copolymers recorded in the Interna- tional Nomenclature of Cosmetics Ingredients inventory system. This substance is utilized in cosmetics, in sunscreens to enhance their water resistance, and is an inert ingredient in pesticides. x Contact sensitization to a close compound VP/eicosene copolymer was also reported. 372.1 Suggested Reading

H C-(H C) 3 2 17 De Groot AC, Bruynzeel DP, Bos JD, van der Meeren HL, van Joost T, Jagtman BA, Weyland JW (1988) The allergens in cos- y x metics. Arch Dermatol 124:1525–1529 N O Scheman A, Cummins R (1998) Contact allergy to PVP/hexadecene copolymer. Contact Der- matitis 39:201 371.1 Suggested Reading

Gallo R, dal Sacco D, Ghigliotti G (2004) Allergic 373 Quaternium-15 contact dermatitis from VP/eicosene copoly- mer (Ganex® V-220) in an emollient cream. N-(3-Chloroallyl)hexaminium Chloride, Hexa- Contact Dermatitis 50:261 methylenetetramine Chloroallyl Chloride, Le Coz CJ, Lefebvre C, Ludmann F, Grosshans E Dowicil 200 (2000) Polyvinylpyrrolidone (PVP)/eicosene CAS Registry Numbers [4080-31-3], [103638- copolymer: an emerging cosmetic allergen. 29-5], and [60789-82-4] Contact Dermatitis 43:61–62 Quaternium-15 is a quaternary ammonium compound, used as a broad-spectrum formalde- hyde-releasing bactericide agent. It is contained as 372 PVP/Hexadecene Copolymer a preservative in cosmetics, toiletries, and aque- ous products. Allergy is mainly due to formalde- CAS Registry Number [32440-50-9] hyde and not to Quaternium-15 itself. PVP/hexadecene copolymer, another PVP Occupational case reports concerned hairdressers, copolymer used for identical applications as a beautician, an engineer working on the mainte- PVP/eicosene copolymer, has been rarely impli- nance of machinery in a chicken processing plant, cated in contact dermatitis. and an employee carrying out photocopying tasks. 158 J.-P. Lepoittevin and C. J. Le Coz

Cl 374.1 Suggested Reading

N Le Coz CJ, Leclere JM, Arnoult E, Raison- Cl Peyron N, Pons-Guiraud A, Vigan M, Mem- bers of Revidal-GERDA (2002) Allergic con- N N tact dermatitis from shellac in mascara. N Contact Dermatitis 46:149–152 Scheman AJ (1998) Contact allergy to 373.1 Suggested Reading quaternium-22 and shellac in mascara. Contact Dermatitis 38:342–343 De Groot A, Coenraads P-J (2010) Twenty-five years quaternium-15 in the European baseline series: does it deserve its place there? Contact 375 Ranitidine Dermatitis 62:210–220 CAS Registry Number [66357-35-5] Finch TM, Prais L, Foulds IS (2001) Occupational Ranitidine Hydrochloride allergic contact dermatitis from quaternium-15 CAS Registry Number [66357-59-3] in an electroencephalography skin preparation Ranitidine, an H2-receptor antagonist, can gel. Contact Dermatitis 44:44–45 cause contact dermatitis within the pharmaceuti- O’Reilly FM, Murphy GM (1996) Occupational cal industry and in health-care workers or may contact dermatitis in a beautician. Contact Der- induce systemic drug reactions in patients. matitis 35:47–48 Tosti A, Piraccini BM, Bardazzi F (1990) Occu- H pational contact dermatitis due to quaternium O H 15. Contact Dermatitis 23:41–42 S N N N Zina AM, Fanan E, Bundino S (2000) Allergic contact dermatitis from formaldehyde and

quaternium-15 in photocopier toner. Contact NO2 Dermatitis 43:241–242

375.1 Suggested Reading 374 Quaternium-22 Martinez MB, Salvador JF, Aguilera GVet al CAS Registry Numbers [51812-80-7] and (2003) Acute generalized exanthematous [82970-95-4] pustulosis induced by ranitidine hydrochlo- This quaternary ammonium compound, used ride. Contact Dermatitis 49:47 as a film former and conditioning agent, was Romaguerra C, Grimalt F, Vilaplana J (1988) Epi- reported as a co-sensitizer in eyelid dermatitis demic of occupational contact dermatitis from due to shellac-based mascara. ranitidine. Contact Dermatitis 18:177–178

OH OH O HO OH 376 Resorcinol NN

OH OH H Cl 1,3-Benzendiol, CI 76505 CAS Registry Number [108-46-3] Resorcinol is used in hairdressing as a modifier (or a coupler) of the PPD group of dyes. It is the least frequent sensitizer in hairdressers. It is also Dictionary of Contact Allergens: Chemical Structures, Sources, and References 159 used in resins, in skin treatment mixtures, and for 378 Sodium Bisulfite tanning. Severe cases of dermatitis due to resor- cinol contained in wart preparations have been Sodium Acid Sulfite, E222 reported. CAS Registry Number [7631-90-5] Sodium bisulfite is mainly used as an antioxi- OH dant in pharmaceutical products, as a disinfectant or bleach, and in the dye industry. The bisulfite of commerce consists chiefly of metabisulfite and possesses the same properties as the true bisulfite. So, the allergen to be tested in products containing OH disulfite is the corresponding metabisulfite.

O 376.1 Suggested Reading S Na Barbaud A, Modiano P, Cocciale M et al (1996) HO O The topical application of resorcinol can pro- voke a systemic allergic reaction. Br J Dermatol 135:1014–1015 378.1 Suggested Reading Frosch PJ, Burrows D, Camarasa JG et al (1993) ’ Allergic reactions to a hairdresser’s series: Budavari S, O Neil MJ, Smith A, Heckelman PE, results from 9 European centres. Contact Der- Kinneary JF (eds) (1996) The Merck Index, matitis 28:180–183 12th edn. Merck, Whitehouse Station, NJ, Tarvainen K (1995) Analysis of patients with USA allergic patch test reactions to a plastics and Garcia-Gavin J, Parente J, Goossens A (2012) glue series. Contact Dermatitis 32:346–351 Allergic contact dermatitis caused by sodium fi Vilaplana J, Romaguera C, Grimalt F (1991) Con- metabisul te: a challenging allergen. A case tact dermatitis from resorcinol in a hair dye. series and literature review. Contact Dermatitis – Contact Dermatitis 24:151–152 67:260 269

377 Silane 379 Sodium Lauryl Sulfate

Monosilane SLS, Sodium Dodecyl Sulfate CAS Registry Number [7803-62-5] CAS Registry Number [151-21-3] Various silane derivatives are used as bonding This anionic detergent is widely used in cos- agents between glass and the resin used as a coat- metics and industry. As a skin irritant agent, SLS can be used in several dermatological applica- ing agent of glass filaments. Organosilanes have been implicated as sensitizers in workers at a glass tions. It is also a good indicator of excited skin filament manufactory. during patch testing.

O SiH O 4 S O

O− Na+ 377.1 Suggested Reading

Heino T, Haapa K, Manelius F (1996) Contact sensitization to organosilane solution in glass filament production. Contact Dermatitis 34:294 160 J.-P. Lepoittevin and C. J. Le Coz

379.1 Suggested Reading 381 Sodium Methyldithiocarbamate Geier J, Uter W, Pirker C et al (2003) Patch testing with the irritant sodium lauryl sulfate (SLS) is Metham-Na, Carbathion, Sodium-N-methyl- useful in interpreting weak reactions to contact dithiocarbamate allergens as allergic or irritant. Contact Derma- CAS Registry Number [137-42-8] titis 48:99–107 Metham-Na is a fungicide nematocide of the dithiocarbamate group. Sensitization occurs among agricultural workers. 380 Sodium Metabisulfite S Sodium Pyrosulfite, Disodium Disulfite, E223 H CAS Registry Number [7681-57-4] N S− This agent is frequently used as a preservative Na+ in pharmaceutical products, in the bread-making industry as an antioxidant, and it can induce con- tact dermatitis. It can be used as a reducing agent 381.1 Suggested Reading in photography and caused dermatitis in a photo- graphic technician, probably acting as an aggra- Koch P (1996) Occupational allergic contact der- fi vating irritative factor. Sodium metabisul te matitis and airborne contact dermatitis from fi contains a certain amount of sodium sul te and 5 fungicides in a vineyard worker. Cross- sodium sulfate. reactions between fungicides of the dithiocar- bamate group? Contact Dermatitis 34:324–329 OO Pambor M, Bloch Y (1985) Dimethoat und S S Dithiocarmabat als berufliche Kontaktallergene − −O O O bei einer Agrotechnikerin. Dermat Monatsschr Na+ Na+ 171:401–405 Schubert H (1978) Contact dermatitis to sodium- N-methyldithiocarbamate. Contact Dermatitis 380.1 Suggested Reading 4:370–371

Acciai MC, Brusi C, Francalanci Giorgini S et al (1993) Allergic contact dermatitis in caterers. 382 Sodium Sulfite Contact Dermatitis 28:48 Garcia-Gavin J, Parente J, Goossens A (2012) E225 Allergic contact dermatitis caused by sodium CAS Registry Number [7757-83-7] fi metabisul te: a challenging allergen. A case Sodium sulfite is mainly used in photographic series and literature review. Contact Dermatitis developers, for fixing prints, bleaching textile – 67:260 269 fibers, as a reducer in manufacturing dyes, as a Jacobs MC, Rycroft RJG (1995) Contact derma- remover of Cl in bleached textiles and paper, and fi titis and asthma from sodium metabisul te in a as a preservative in the food industry for meat, egg photographic technician. Contact Dermatitis yolks, and so on. 33:65–66 Sasseville D, El-Helou T (2009) Occupational allergic contact dermatitis from sodium meta- bisulfite. Contact Dermatitis 61:244–245 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 161

O 384 Sorbitan Sesquioleate

S −O O− Sorbitan 9-Octadecenoate (2:3), Arlacel 83, Na+ Na+ Anhydrohexitol Sesquioleate CAS Registry Number [8007-43-0], [37318- 79-9] 382.1 Suggested Reading Sorbitan sesquioleate is a mixture of mono- and diesters of oleic acid and extol anhydrides Budavari S, O’Neil MJ, Smith A, Heckelman PE, derived from . It is used as a surfactant Kinneary JF (eds) (1996) The Merck Index, and an emulsifier in cosmetics. It acts sometimes 12th edn. Merck, Whitehouse Station as a contact allergen, particularly in leg ulcer Vena GA, Foti C, Angelini G (1994) Sulfite con- patients. It is also responsible for false-positive tact allergy. Contact Dermatitis 31:172–175 patch test reactions to haptens, with which some allergen providers emulgated, such as parabens mix, fragrance mix, Amerchol L101, and ethylene 383 Solvent Red 23 urea/melamine formaldehyde.

Sudan III, CI 26100, D and C Red No. 17 O CAS Registry Number [85-86-9] Solvent Red 23 is an oil-soluble red azo dye HO used in cosmetic products in Japan. Cases were OH OH reported in hairdressers, who also reacted to PPD OH (the molecule is likely to be hydrolyzed into PPD) HO and to p-aminoazobenzene. One case of contact OH OH dermatitis was reported in the metal industry.

384.1 Suggested Reading

Orton DI, Shaw S (2001) Sorbitan sesquioleate as an allergen. Contact Dermatitis 44:190–191 N Pasche-Koo F, Piletta PA, Hunziker N et al (1994) N High sensitization rate to emulsifiers in N OH patients with chronic leg ulcers. Contact Der- N matitis 31:226–228

385 Spectinomycin 383.1 Suggested Reading CAS Registry Number [1695-77-8] Fregert S (1967) Allergic contact dermatitis due to Spectinomycin is an aminocyclitol antibiotic. fumes from burning alcohol containing an It is used in human medicine against Neisseria azo-dye. Contact Dermatitis Newslett 1:11 gonorrhoeae and in veterinary medicine, espe- Matsunaga K, Hayakawa R, Yoshimura K et al cially for poultry, pigs, and cattle. Cases of der- (1990) Patch-test-positive reactions to Solvent matitis have been reported in veterinary practice. Red 23 in hairdressers. Contact Dermatitis 23:266 162 J.-P. Lepoittevin and C. J. Le Coz

H OH 387 Tetrabutylthiuram Disulfide H H O O CH3 TBTD H3C CAS [1634-02-2] TBTD is a rubber vulcanization accelerator. HO O H OH O N S H3C N S N N S

385.1 Suggested Reading S

Dal Monte A, Laffi G, Mancini G (1994) Occu- pational contact dermatitis due to spectinomy- 387.1 Suggested Reading cin. Contact Dermatitis 31:204–205 Vilaplana J, Romaguera C, Grimalt F (1991) Con- Le Coz CJ (2004) Fiche d’éviction en cas tact dermatitis from lincomycin and spectino- d’hypersensibilité au thiuram mix. Ann mycin in chicken vaccinators. Contact Dermatol Venereol 131:1012–1014 Dermatitis 24:225–226

388 Tetrabutylthiuram Monosulfide 386 Tetrabenzylthiuram Disulfide TBTM TBzTD CAS Registry Number [97-74-5] CAS Registry Number [10591-85-2] TBTM is a rubber vulcanization accelerator. TBzTD is a rubber vulcanization accelerator.

S S

N S N

S

N S S N

S 388.1 Suggested Reading

Le Coz CJ (2004) Fiche d’éviction en cas d’hypersensibilité au thiuram mix. Ann Dermatol Venereol 131:1012–1014 386.1 Suggested Reading 389 Tetrachloroacetophenone Le Coz CJ (2004) Fiche d’éviction en cas ’ d hypersensibilité au thiuram mix. Ann CAS Registry Number [39751-78-5] – Dermatol Venereol 131:1012 1014 Tetrachloroacetophone was combined with tri- ethyl phosphate to form an organophosphate insecticide. It induced contact dermatitis in a pro- cess operator in an insecticide plant. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 163

O O implanted disulfiram. Contact Dermatitis 43 (4):246–247 Cl Mathelier-Fusade P, Leynadier F (1994) Occupa- tional allergic contact reaction to disulfiram. Cl Contact Dermatitis 31:121–122 Cl Pföhler C, Körner R, Müller CS et al (2011) Occupational allergic contact dermatitis of the ears caused by thiurams in a headset. Contact 389.1 Suggested Reading Dermatitis 65:242–243 Van Joost T, Wiemer GR (1991) Contact derma- titis from tetrachloroacetophenone (TCAP) in 391 Tetraethylthiuram Monosulfide an insecticide plant. Contact Dermatitis 25:66–67 Sulfiram, TETM, Tetraethylthiodicarbonic Diamide CAS Registry Number [95-05-6] 390 Tetraethylthiuram Disulfide This rubber vulcanization accelerator is also used as an ectoparasiticide against Sarcoptes Disulfiram, TETD, Antabuse, Esperal® scabiei, louses, or in veterinary medicine. CAS Registry Number [97-77-8] TETD is a rubber accelerator of the thiuram S S group, contained in “thiuram mix.” It can cross- react with other thiurams, especially TMTD. N SN TETD is used to aid those trying to break their dependence on alcohol. The disulfiram-alcohol reaction is not allergic but is due to the accumula- tion of toxic levels of acetaldehyde. The implanted drug can, however, lead to local or generalized 391.1 Suggested Reading dermatitis, for example, ingested disulfiram, mainly in previously rubber-sensitized patients. Le Coz CJ (2004) Fiche d’éviction en cas As an adjunctive treatment of alcoholism, it caused d’hypersensibilité au thiuram mix. Ann occupational contact dermatitis in a nurse. Dermatol Venereol 131:1012–1014

S 392 Tetraglycidyl- S N 4,40-methylenedianiline N S (TGMDA) S 4,40-Methylenebis(N,N-diglycidylaniline) CAS Registry Number [28768-32-3] 0 390.1 Suggested Reading Tetraglycidyl-4-4 -methylenedianiline (TGMDA) is an epoxy component of glues used in the aircraft industry. Such resin systems are Condé-Salazar L, Del-Rio E, Guimaraens D et al present in pre-impregnated composite materials (1993) Type IV allergy to rubber additives: a (prepregs). It can be used in association with 10-year study of 686 cases. J Am Acad triglycidyl-p-aminophenol (TGPAP) and N-N0- Dermatol 29:176–180 diglycidylaniline (DGA). Kiec-Swierczynska M, Krecisz B, Fabicka B (2000) Systemic contact dermatitis from 164 J.-P. Lepoittevin and C. J. Le Coz

394 Tetramethylthiuram Disulfide

Thiram, TMTD CAS Registry Number [137-26-8] This rubber chemical, accelerator of vulcani- zation, represents the most commonly positive allergen contained in “thiuram mix.” The most frequent occupational categories are the metal industry, homemakers, health services and labo- ratories, the building industry, and shoemakers. It 392.1 Suggested Reading is also widely used as a fungicide, belonging to the dithiocarbamate group of carrots, bulbs, and Jappe U, Geier J, Hausen BM (2005) Contact woods, and as an insecticide. Thiram is the agri- vitiligo following a strong patch test reaction cultural name for thiuram. to triglycidyl-p-aminophenol in an aircraft industry worker: case report and review of the S literature. Contact Dermatitis 53:89–92 S N Pesonen M, Suuronen K, Jolanki R et al (2015) N S Occupational contact dermatitis caused by ani- line epoxy resins in the air craft industry. Con- S tact Dermatitis 73:113–118 394.1 Suggested Reading 393 Tetraisobutylthiuram Disulfide Condé-Salazar L, Guimaraens D, Villegas C et al (1995) Occupational allergic contact dermatitis TITD, Thioperoxydicarbonic Diamide, Tetrakis in construction workers. Contact Dermatitis (2-Methylpropyl) 35:226–230 CAS Registry Number [137-26-8] Kiec-Swierczynska M (1995) Occupational sen- TITD is a rubber vulcanization accelerator. sitivity to rubber. Contact Dermatitis 32:171–172 S Mancuso G, Reggiani M, Berdondini RM (1996) Occupational dermatitis in shoemakers. Con- S N – N S tact Dermatitis 34:17 22 Pföhler C, Körner R, Müller CS et al (2011) S Occupational allergic contact dermatitis of the ears caused by thiurams in a headset. Contact Dermatitis 65:242–243 393.1 Suggested Reading Sharma VK, Kaur S (1990) Contact sensitization by pesticides in farmers. Contact Dermatitis Le Coz CJ (2004) Fiche d’éviction en cas 23:77–80 d’hypersensibilité au thiuram mix. Ann Dermatol Venereol 131:1012–1014 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 165

395 Tetramethylthiuram Monosulfide O

N TMTM CAS Registry Number [97-74-5] This rubber accelerator is contained in N “thiuram mix.” The most frequent occupational categories are the metal industry, homemakers, CI health services and laboratories, and the building industry.

396.1 Suggested Reading

Hulst KV, Kerre S, Goossens A (2010) Occupa- tional allergic contact dermatitis from tetra- zepam in nurses. Contact Dermatitis – 395.1 Suggested Reading 62:303 308 Swinnen I, Ghys K, Kerre S, et al (2013) Occu- pational airborne contact dermatitis from ben- Condé-Salazar L, Del-Rio E, Guimaraens D et al zodiazepines and other drugs. Contact (1993) Type IV allergy to rubber additives: a Dermatitis 70:227–232 10-year study of 686 cases. J Am Acad Dermatol 29:176–180 Condé-Salazar L, Guimaraens D, Villegas C et al (1995) Occupational allergic contact dermatitis 397 Thebaine in construction workers. Contact Dermatitis CAS Registry Number [115-37-7] 35:226–230 The naturally occurring opiate alkaloid Le Coz CJ (2004) Fiche d’éviction en cas thebaine is present in concentrated poppy straw d’hypersensibilité au thiuram mix. Ann and in small concentrations in codeine alkaloid. It Dermatol Venereol 131:1012–1014 is used in the manufacture of other opiate phar- Pföhler C, Körner R, Müller CS et al (2011) maceuticals, such as buprenorphine and mor- Occupational allergic contact dermatitis of the phine, and caused contact dermatitis in a ears caused by thiurams in a headset. Contact laboratory worker at an opiates manufacturing Dermatitis 65:242–243 pharmaceutical company, also sensitive to codeine. 396 Tetrazepam O CAS Registry Number [10379-14-3] Tetrazepam is a benzodiazepine compound used systemically as a myorelaxant. It may induce skin rashes such as maculopapular eruption, O Stevens-Johnson syndrome, or photosensitivity. Occupational sensitization can be observed in N pharmaceutical plants. Sensitization generally O does not concern other benzodiazepines. 166 J.-P. Lepoittevin and C. J. Le Coz

397.1 Suggested Reading especially in contact lens fluids, eyedrops, and vaccines. The ethylmercuric moiety is the major Dekeyser S, van Tomme M, Boone B et al (2017) allergenic determinant, sometimes associated Occupational allergic contact dermatitis with mercury sensitivity. Thiomersal is an indica- caused by thebaine and oripavine. Contact tor of photosensitivity to piroxicam, through its Dermatitis 76:120 thiosalicylic moiety. Waclawski ER, Aldridge R (1995) Occupational dermatitis from thebaine and codeine. Contact - + Dermatitis 33:51 COO Na

Hg 398 Thiabendazole S

CAS Registry Number [148-79-8] This fungicide and vermifuge agent is widely 399.1 Suggested Reading used in agriculture (e.g., forcitrus fruits) and in medical and veterinary practice as an Arévalo A, Blancas R, Ancona A (1995) Occupa- anthelmintic drug. tional contact dermatitis from piroxicam. Am J Contact Dermat 6:113–114 H De Groot AC, van Wijnen WG, van Wijnen-Vos M (1990) Occupational contact dermatitis of N N the eyelids, without ocular involvement, from fl S thimerosal in contact lens uid. Contact Der- N matitis 23:195 Kiec-Swierczynska M, Krecisz B, Swierczynska- Machura D (2003) Occupational allergic con- 398.1 Suggested Reading tact dermatitis due to thimerosal. Contact Der- matitis 48:337–338 Izu R, Aguirre A, Goicoechea A et al (1993) Photoaggravated allergic contact dermatitis due to topical thiabendazole. Contact Derma- 400 Thioctic Acid titis 28:243–244 Mancuso G, Staffa M, Errani A et al (1990) Occu- Alpha-lipoic acid, 1,2-Dithiolane-3-pentanoic pational dermatitis in animal feed mill workers. acid Contact Dermatitis 22:37–41 CAS Registry Number [1077-28-7] Thioctic acid or α-lipoic acid has been identi- fied as a potentially important sensitizer in cos- 399 Thimerosal metics such as “antiaging” creams due to its antioxidant properties. Thiomersal, Thiomersalate, Merthiolate, Mercurothiolic Acid Sodium Salt CAS Registry Number [54-64-8] Thiomersal is an organic mercury salt prepared by reacting ethylmercuric chloride (or ethylmercuric hydroxide) with thiosalicylic acid. It is still used as a disinfectant and a preser- vative agent but less commonly than previously, Dictionary of Contact Allergens: Chemical Structures, Sources, and References 167

400.1 Suggested Reading cedar (Calocedrus decurrens Florin) used for pen- cils, chests or toys, and western cedar (Thuja Bergqvist-Karlsson A, Thelin I, Bergendorff O plicata Donn.) as used for hard realizations such (2006) Contact dermatitis to α-lipoic acid in as construction or boats. an anti-wrinkle cream. Contact Dermatitis 55:56–57 O Leysen J, Aerts O (2016) Further evidence of thioctic acid (α-lipoiv acid) being a strong cos- metic sensitizer. Contact Dermatitis 74:182–184

O 401 Thiourea

Thiocarbamide 402.1 Suggested Reading CAS Registry Number [62-56-6] Thiourea is used as a cleaner agent for silver Hausen BM (2000) Woods. In: Kanerva L, and copper and as an antioxidant in diazo copy Elsner P, Wahlberg JE, Maibach HI (eds) paper. It can induce (photo)contact dermatitis. Handbook of occupational dermatology. Springer, Berlin/Heidelberg/New York, pp S 771–780 Lamminpää A, Estlander T, Jolanki R et al (1996) H H NN Occupational allergic contact dermatitis caused by decorative plants. Contact Dermati- H H tis 34:330–335

401.1 Suggested Reading 403 Timolol

Dooms-Goossens A, Debusschère K, Morren M CAS Registry Number [26839-75-8] et al (1988) Silver polish: another source of Timolol was implicated in allergic contact der- contact dermatitis reactions to thiourea. Con- matitis due to beta-blocker agents in eyedrops. tact Dermatitis 19:133–135 Geier J, Fuchs T (1993) Contact allergy due to S 4-N,N-dimethylaminobenzene diazonium N N chloride and thiourea in diazo copy paper. Contact Dermatitis 28:304–305 N O N Kanerva L, Estlander T, Jolanki R (1994) Occu- H pational allergic contact dermatitis caused by O OH thiourea compounds. Contact Dermatitis 31:242–248 403.1 Suggested Reading

402 Thymoquinone Giordano-Labadie F, Lepoittevin JP, Calix I et al (1997) Allergie de contact aux ^a-bloqueurs des CAS Registry Number [490-91-5] collyres: allergie croisée? Ann Dermatol Thymoquinone is an allergen in different cedar Venereol 124:322–324 species, Cupressaceae family, such as incense 168 J.-P. Lepoittevin and C. J. Le Coz

Horcajada-Reales C, Rodriguez-Soria VJ, Suàrez- 404.1 Suggested Reading Fernàndez R (2015) Allergic contact dermatitis caused by timolol with cross-sensitivity to Le Coz CJ (2002) Fiche d’éviction en cas levobunolol. Contact Dermatitis 73:368–369 d’hypersensibilité au pivalate de tixocortol. Ann Dermatol Venereol 129:348–349 Lepoittevin JP, Drieghe J, Dooms-Goossens A 404 (1995) Studies in patients with corticosteroid contact allergy. Understanding cross-reactivity Tixocortol 21-pivalate, Tixocortol 21-trimethy- among different steroids. Arch Dermatol lacetate 131:31–37 CAS Registry Number [55560-96-8] Shaw DW, Maibach HI (2013) Clinical relevance Tixocortol 21-pivalate is a 21-ester of of tixocortol pivalate-positive patch tests and tixocortol, widely used in topical treatments. It questionable bioequivalence of different can induce severe allergic contact dermatitis. hydrocortisone preparations. Contact Dermati- This corticosteroid is a marker of the allergenic tis 68:369–375 A group that includes molecules without major substitution on the D cycle (no C16 methylation, no C17 side chain). A short-chain C21 ester is 405 Tocopherol, Tocopheryl possible. Molecules are , , Acetate (DL-, D-) fludrocortisone, fluorometholone, hydrocorti- sone, methylprednisolone, methylprednisone, Vitamin E , , tixocortol, and their CAS Registry Number [1406-66-2]

C21 esters (acetate, caproate or hexanoate, phos- Vitamin E Acetate DL, Vitamin E Acetate D phate, pivalate or trimethylacetate, succinate or CAS Registry Number [7695-91-2] and CAS hemisuccinate, m-sulfobenzoate). Registry Number [58-95-7] Tocopherol and tocopheryl acetate are used mainly as antioxidants. Tocopheryl acetate, an ester of tocopherol (vitamin E), can induce aller- gic contact dermatitis. O S O

O HO HO OH

405.1 Suggested Reading

De Groot AC, Berretty PJ, van Ginkel CJ et al O (1991) Allergic contact dermatitis from tocopheryl acetate in cosmetic creams. Contact Dermatitis 25:302–304 Matsumura T, Nakada T, Iijima M (2004) Wide- spread contact dermatitis from tocopherol ace- tate. Contact Dermatitis 51:211–212 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 169

406 Toluene-2,5-Diamine foams, paints, lacquers, adhesives, binding agents, synthetics rubbers, and elastomeric fibers. p-Toluylenediamine, p-Toluenediamine CAS Registry Number [95-70-5] NCO Toluene-2,5-diamine is a permanent hair dye NCO involved in contact dermatitis in hairdressers and consumers. It does not cross-react with PPD, but cosensitization is frequent.

NCO NCO 2,4-TDI 2,6-TDI NH2

407.1 Suggested Reading H2N Estlander T, Keskinen H, Jolanki R et al (1992) 406.1 Suggested Reading Occupational dermatitis from exposure to polyurethane chemicals. Contact Dermatitis – Frosch PJ, Burrows D, Camarasa JG et al (1993) 27:161 165 Allergic reactions to a hairdresser’s series: Le Coz CJ, El Aboubi S, Ball C (1999) Active results from 9 European centres. Contact Der- sensitization to toluene di-isocyanate. Contact – matitis 28:180–183 Dermatitis 41:104 105 Guerra L, Tosti A, Bardazzi F et al (1992) Contact dermatitis in hairdressers: the Italian experi- ence. Gruppo Italiano Ricerca Dermatiti da 408 Tosyl Chloride Contatto e Ambientali. Contact Dermatitis 26:101–107 p-Toluene Sulfonyl Chloride, p-Toluene Le Coz CJ, Lefebvre C, Keller F et al (2000) Sulfochloride Allergic contact dermatitis caused by skin CAS Registry Number [98-59-9] painting (pseudotattooing) with black henna, Tosyl chloride is used mainly in the prepara- a mixture of henna and p-phenylenediamine tion of chemical derivatives in the pharmaceuti- and its derivatives. Arch Dermatol cal, plastics, and organic chemical industries. 136:1515–1517 OO S Cl 407 Toluene Diisocyanate

Toluene Diisocyanate (Mixture) CAS Registry Number [26471-62-5] Toluene 2,4-Diisocyanate 408.1 Suggested Reading CAS Registry Number [584-84-9] Toluene 2,6-Diisocyanate Watsky KL, Reynolds K, Berube D et al (1993) CAS Registry Number [91-08-7] Occupational contact dermatitis from tosyl Toluene diisocyanate is a mixture of 2,4-TDI chloride in a chemist. Contact Dermatitis and 2,6-TDI. It is used in the manufacture of 29:211–212 various polyurethane products: elastic and rigid 170 J.-P. Lepoittevin and C. J. Le Coz

409 Triacetin Endo H, Kawada A, Yudate T et al (1999). Drug eruption due to tribenoside. Contact Dermatitis Glyceryl Triacetate 41:223 CAS Registry Number [102-76-1] Triacetin is a component of cigarette filters, which induced a contact dermatitis in a worker 411 Tributyltin Oxide at a cigarette manufactory. CAS Registry Number [56-35-9] Tributyltin oxide is used as an antifouling and AcO OAc biocide agent against fungi, algae, and bacteria, OAc particularly in paints. Sometimes used in chemis- try, tributyltin oxide is a strong irritant.

409.1 Suggested Reading

Unna PJ, Schulz KH (1963) Allergisches Kontaktekzem durch Triacetin. Hautarzt 14:423–425 O Sn Sn

410 Tribenoside

CAS Registry Number [10310-32-4] This drug is used for the treatment, both topical and oral, of hemorrhoids. It leads to benzoïc acid, which is contained in Myroxylon pereirae as well, 411.1 Suggested Reading and could be the sensitizer. Goh CL (1985) Irritant dermatitis from tri- N- butyl tin oxide in paint. Contact Dermatitis 12:161–163 Grace CT, Ng SK, Cheong LL (1991) Recurrent irritant contact dermatitis due to tributyltin O oxide on work clothes. Contact Dermatitis – O 25:250 251 O O

O OH 412 Trichloroethane

1,1,1-Trichloroethane, Methylchloroform CAS Registry Numbers [71-55-6] and [25323- 89-1] Trichloroethane is a solvent that has wide applications in industry, such as for cold type 410.1 Suggested Reading metal cleaning and in cleaning plastic molds. It is mainly an irritant but can also provoke allergic Inoue A, Tamagawa-Mineoka R, Katoh N et al contact dermatitis. (2009) Allergic contact dermatitis caused by tribenoside. Contact Dermatitis 60:349–350 Dictionary of Contact Allergens: Chemical Structures, Sources, and References 171

Cl This emulsifying agent can be contained in Cl Cl many products such as cosmetics, topical medi- cines, metalworking cutting fluids, and color film developers. Traces may exist in other ethanol- amines such as mono- and diethanolamine. Contact allergy seems to be rarer than previously thought. 412.1 Suggested Reading

OH Mallon J, Tek Chu M, Maibach HI (2001) Occu- pational allergic contact dermatitis from methyl chloroform (1,1,1-trichloroethane)? Contact Dermatitis 45:107 N OH

413 Trichloroethylene HO

Trilene, Triclene, Trethylene 414.1 Suggested Reading CAS Registry Number [79-01-6] Trichloroethylene is a chlorinated hydrocarbon Blum A, Lischka G (1997) Allergic contact der- used as a detergent or solvent for metals, oils, matitis from mono-, di- and triethanolamine. resins, sulfur, and as general degreasing agent. It Contact Dermatitis 36:166 can cause irritant contact dermatitis, generalized Le Coz CJ, Scrivener Y, Santinelli F et al (1998) exanthema, Stevens-Johnson-like syndrome, pus- Sensibilisation de contact au cours des ulcères tular or bullous eruption, scleroderma, as well as de jambe. Ann Dermatol Venereol neurological and hepatic disorders. 125:694–699 Scheman AJ, Katta R (1997) Photographic aller- Cl H gens: an update. Contact Dermatitis 37:130 HCl Cl H 415 Triethylenetetramine

413.1 Suggested Reading CAS Registry Number [112-24-3] Triethylenetetramine is used as an amine hard- Goon AT, Lee LT, Tay YK et al (2001) A case of ener in epoxy resins of the bisphenol A type. trichloroethylene hypersensitivity syndrome. Cross-sensitivity is possible with Arch Dermatol 137:274–276 diethylenetriamine and diethylenediamine. Puerschel WC, Odia SG, Rakoski J et al (1996) Trichloroethylene and concomitant contact H H dermatitis in an art painter. Contact Dermatitis N N H 34:430–431 H N N

H H 414 Triethanolamine

Trolamine 415.1 Suggested Reading CAS Registry Number [102-71-6] Aalto-Korte K, Pesonen M, Suuronen K (2015) Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, 172 J.-P. Lepoittevin and C. J. Le Coz

sensitizing products and diagnosis. Contact Dermatitis 73:336–342 Jolanki R, Kanerva L, Estlander T et al (1990) Occupational dermatoses from epoxy resin compounds. Contact Dermatitis 23:172–183

416 Triforine

Saprol®, 1,4-bis(2,2,2-Trichloro-1-formamidoe- 417.1 Suggested Reading thyl)piperazine CAS Registry Number [26644-46-2] Jappe U, Geier J, Hausen BM (2005) Contact This pesticide is widely used in flower grow- vitiligo following a strong patch test reaction ing. Cross-reactions are expected to dichlorvos. to triglycidyl-p-aminophenol in an aircraft industry worker: case report and review of the literature. Contact Dermatitis 53:89–92 CCl3 H Pesonen M, Suuronen K, Jolanki R et al (2015) Occupational contact dermatitis caused by ani- H N N O line epoxy resins in the air craft industry. Con- – O N N H tact Dermatitis 73:113 118

H CCl 3 418 Triglycidyl Isocyanurate

1,3,5-Triglycidyl-s-triazinetrione 416.1 Suggested Reading CAS Registry Number [2451-62-9] Triglycidyl isocyanurate is a triazine epoxy Ueda A, Aoyama K, Manda F et al (1994) compound used as a resin hardener in polyester Delayed-type allergenicity of triforine powder paints, in the plastics industry, resin mold- (Saprol®). Contact Dermatitis 31:140–145 ing systems, inks, and adhesives. Occupational contact dermatitis can occur in people producing 417 Triglycidyl-p-Aminophenol this chemical, in those producing the powder coat (TGPAP) paint, and in sprayers. Respiratory symptoms have been observed. N,N0-Diglycidyl-4-glycidyloxyaniline O CAS Registry Number [5026-74-4] Triglycidyl-p-aminophenol (TGPAP) is an O epoxy component of glues used in the aircraft industry. Such resin systems are present in N N pre-impregnated composite materials (prepregs). O It can be used in association with tetraglycidyl-4- N 40-methylenedianiline (TGMDA) and N-N0- O O diglycidylaniline (DGA).

O Dictionary of Contact Allergens: Chemical Structures, Sources, and References 173

418.1 Suggested Reading Toffoletto F, Cortona G, Feltrin G et al (1994) Occupational contact dermatitis from amine- Erikstam U, Bruze M, Goossens A (2001) Degra- functional methoxysilane in continuous-glass- dation of triglycidyl isocyanurate as a cause of filament production. Contact Dermatitis false-negative patch test reaction. Contact Der- 31:320–321 matitis 44:13–17 Foulds IS, Koh D (1992) Allergic contact derma- titis from resin hardeners during the manufac- 420 N-(3-Trimethoxysilylpropyl)- ture of thermosetting coating paints. Contact Ethylenediamine Dermatitis 26:87–90 McFadden JP, Rycroft RJG (1993) Occupational Z 6020 contact dermatitis from triglycidyl iso- CAS Registry Number [1760-24-3] cyanurate in a powder paint sprayer. Contact This amine-functional methoxysilane, Dermatitis 28:251 referenced as aminoethyl aminopropyltri- Munro CS, Lawrence CM (1992) Occupational methoxysilane, was implicated in the production contact dermatitis from triglycidyl iso- of glass filaments. cyanurate in a powder paint factory. Contact Dermatitis 26:59 O H N Si N H2N O 419 -[3-(Trimethoxysilyl)propyl]- O N-(vinylbenzyl) ethylenediamine Monohydrochloride 420.1 Suggested Reading

1,2-Ethanediamine, N-[(Ethenylphenyl)methyl]-N- Heino T, Haapa K, Manelius F (1996) Contact [3-(trimethoxysilyl)propyl]-, Monohydrochloride sensitization to organosilane solution in glass fi CAS Registry Number [34937-00-3] lament production. Contact Dermatitis This amine-functional methoxysilane silane 34:294 compound, referenced as vinylbenzylaminoethyl aminopropyltrimethoxysilane, was implicated in the production of glass filaments. 421 2,4,6-Trimethylol Phenol

O CAS Registry Number [2937-61-3] H Trimethylol phenol is an allergen in resins N Si N O based on phenol and formaldehyde. Cross- H O reactivity is possible with other phenol-derivative molecules. HCl OH OH

OH 419.1 Suggested Reading

Heino T, Haapa K, Manelius F (1996) Contact sensitization to organosilane solution in glass filament production. Contact Dermatitis 34:294 HO 174 J.-P. Lepoittevin and C. J. Le Coz

421.1 Suggested Reading

Bruze M, Zimerson E (1997) Cross-reaction pat- terns in patients with contact allergy to simple O HO O methylol phenols. Contact Dermatitis 37:82–86 O O Bruze M, Fregert S, Zimerson E (1985) Contact Tulipalin A Tulipalin B allergy to phenol-formaldehyde resins. Contact Dermatitis 12:81–86 423.1 Suggested Reading Bruynzeel DP (1997) Bulb dermatitis. Dermato- fl 422 Trimethylthiourea logical problems in the ower bulb industries. Contact Dermatitis 37:70–77 Gette MT, Marks JE (1990) Tulip fingers. Arch CAS Registry Number [2489-77-2] Dermatol 126:203–205 Trimethylthiourea is a thiourea derivative used, for example, for polychloroprene (neoprene) rub- ber vulcanization. Patients sensitized to ethylbutyl thiourea can also react to trimethylthiourea. 424 Tuliposide A CAS Registry Number [19870-30-5] S Tuliposide A is a glucoside prohapten contained in tulip bulbs and in Alstroemeria NN H (Tulipa spp., Alstroemeria spp., Lilium spp.). It is rapidly hydrolyzed to tulipalin A and represents a common occupational problem among workers in the European tulip industry. Tuliposide can be 422.1 Suggested Reading present as 1-tuliposide A but is more frequently identified as 6-tuliposide A. Kanerva L, Estlander T, Jolanki R (1994) Occu- pational allergic contact dermatitis caused by H OH thiourea compounds. Contact Dermatitis 31:242–248 H O HO HO O H OH 423 Tulipalin A and Tulipalin B H H OOH α-Methylene-γ-butyrolactone and β-Hydroxy- α-methylene-γ-butyrolactone 424.1 Suggested Reading CAS Registry Number [547-65-9] and CAS Registry Number [38965-80-9] Christensen LP, Kristiansen K (1995) A simple Tulipalin A is the unsubstituted α-methylene- HPLC method for the isolation and quantifica- γ-butyrolactone contained in the sap of damaged tion of the allergens tuliposide A and tulipalin tulips (Liliaceae family) and Alstroemeria AinAlstroemeria. Contact Dermatitis (Alstroemeriaceae family). Tulipalin B, due to 32:199–203 hydrolysis of tuliposide B, seems to have a weak Gette MT, Marks JE (1990) Tulip fingers. Arch sensitizing capacity. Dermatol 126:203–205 Lamminpää A, Estlander T, Jolanki R et al (1996) Occupational allergic contact dermatitis Dictionary of Contact Allergens: Chemical Structures, Sources, and References 175

caused by decorative plants. Contact Dermati- in the sap of the Anacardiaceae family such as tis 34:330–335 Toxicodendron radicans Kuntze (poison ivy) or Anacardium occidentale L. (cashew nut tree). The R-side chain generally includes 13, 15, or 17 car-

425 Tylosin bons. A urushiol with a C15 side chain is named pentadecylcatechol (a term sometimes employed CAS Registry Number [1401-69-0] in medical literature for poison ivy urushiol), and

Tylosin is a macrolid antibiotic used in veteri- a urushiol with a C17 side chain is a hepta- nary medicine. Occupational exposure concerns decylcatechol (mostly encountered in poison oak farmers, breeders, animal feed workers, and urushiol). veterinarians. OH

425.1 Suggested Reading OH

Barbera E, de la Cuadra J (1989) Occupational R airborne allergic contact dermatitis from tylosin. Contact Dermatitis 20:308–309 fi Cara ni S, Assalve D, Stingeni L et al (1994) 426.1 Suggested Reading Tylosin, an airborne contact allergen in veteri- narians. Contact Dermatitis 31:327–328 Epstein WL (1994) Occupational poison ivy and Guerra L, Venturo N, Tardio M et al (1991) Air- oak dermatitis. Dermatol Clin 12:511–516 borne contact dermatitis from animal feed anti- Kawai K, Nakagawa M, Kawai K et al (1991) biotics. Contact Dermatitis 25:333–334 Hyposensitization to urushiol among Japanese Tuomi ML, Räsänen L (1995) Contact allergy to lacquer craftsmen. Contact Dermatitis tylosin and cobalt in a pig-farmer. Contact 24:146–147 Dermatitis 33:285 Kullavanijaya P, Ophaswongse S (1997) A study of dermatitis in the lacquerware industry. Con- tact Dermatitis 36:244–246 426 Urushiol

CAS Registry Numbers [492-89-7] and [53237- 59-5] Urushiol is a generic name that indicates a mixture of several close alkylcatechols contained

O

CHO

N O HO O OH HO O O O O OCH3 OH OCH3 O O OH 176 J.-P. Lepoittevin and C. J. Le Coz

427 Usnic Acid (d-Usnic Acid, l-Usnic N Acid) N

CAS Registry Number [125-46-2] (CAS Registry 2-VP 4-VP Number [7562-61-0], CAS Registry Number [6159-66-6]) Usnic acid is a component of lichens, also used 428.1 Suggested Reading as a topical antibiotic. Allergic contact dermatitis from lichens occurs mainly occupationally in for- Bergendorff O, Wallengren J (1999) estry and horticultural workers and in lichen 4-Vinylpyridine-induced dermatitis in a labo- pickers. ratory worker. Contact Dermatitis 40:280–281 Foussereau J, Lantz JP, Grosshans E (1972) Aller- O gic eczema from vinyl-4-pyridine. Contact OH O Dermatitis Newslett 11:261 Sasseville D, Balbul A, Kwong P et al (1996) Contact sensitization to pyridine derivatives. HO O Contact Dermatitis 35:101–102 O

O 429 Virginiamycin

CAS Registry Number [11006-76-1] 427.1 Suggested Reading Virginiamycin S1: Staphylomycin S CAS Registry Number [23152-29-6] Aalto-Korte K, Lauerma A, Alanko K (2005) Virginiamycin M1: Pristinamycin IIA, Occupational allergic contact dermatitis from Mikamycin A, Ostreogrycin A, Staphylomycin lichens in present-day Finland. Contact Der- M1, Streptogramin A, Vernamycin A matitis 52:36–38 CAS Registry Number [21411-53-0] Hahn M, Lischka G, Pfeifle J et al (1995) A case Like the other streptogramin, pristinamycin, of contact dermatitis from lichens in southern virginiamycin is made of two subunits, Germany. Contact Dermatitis 32:55–56 virginiamycin S1 and virginiamycin M1. Derma- titis was quite common in people using the for- merly available topical virginiamycin. 428 Vinylpyridine Occupational dermatitis was observed in the phar- maceutical industry, in breeders, and in a surgeon 2-Vinylpyridine who used topical virginiamycin on postoperative CAS Registry Number [100-69-6] wounds (personal observation). 4-Vinylpyridine CAS Registry Number [100-43-6] 4-Vinylpyridine was used as a monomer in polymer chemistry and induced non- immunological contact urticaria and allergic con- tact dermatitis. No cross-reactivity is observed between pyridine derivatives. Dictionary of Contact Allergens: Chemical Structures, Sources, and References 177

S S

HO N Zn N SSN H3C O O O HC C N C C N H H3C CH H O O HC CH3 H C NNCCCH 430.1 Suggested Reading O H Condé-Salazar L, Del-Rio E, Guimaraens D et al O (1993) Type IV allergy to rubber additives: a 10-year study of 686 cases. J Am Acad H – N Dermatol 29:176 180 Condé-Salazar L, Guimaraens D, Villegas C et al OH O (1995) Occupational allergic contact dermatitis in construction workers. Contact Dermatitis O 35:226–230 O Kiec-Swierczynska M (19959 Occupational sen- N O sitivity to rubber. Contact Dermatitis N O 32:171–172

O 431 Zinc bis- 429.1 Suggested Reading Diethyldithiocarbamate

Blancas-Espinosa L, Conde-Salazar L, Pérez- Zinc N,N-Diethyldithiocarbamate, Diethyldithioca- Hortet C (2006) Occupational airborne contact rbamic Acid Zinc Salt dermatitis from pristinamycin. Contact Derma- CAS Registry Number [14324-55-1] titis 54:63–65 Diethyldithiocarbamate zinc is a rubber com- Rudzki E, Rebandel P (1984) Contact sensitivity ponent used as a vulcanization accelerator. Oxi- to antibiotics. Contact Dermatitis 11:41–42 dation of this carbamate leads to tetraethylthiuram Tennstedt D, Dumont-Fruytier M, Lachapelle JM disulfide. It can be responsible for rubber derma- (1978) Occupational allergic contact dermatitis titis in health personnel. It was contained in “carba to virginiamycin, an antibiotic used as a food mix.” additive for pigs and poultry. Contact Derma- titis 4:133–134 S S Zn N SNS 430 Zinc bis-Dibutyldithiocarbamate

Zinc N,N-Dibutyldithiocarbamate CAS Registry Number [136-23-2] A rubber chemical, used as a vulcanization 431.1 Suggested Reading accelerator. It can also be contained in paints, glue removers, and anticorrosive. It was contained Chipinda I, Hettick JM, Simoyi RH et al (2008) in “carba mix.” Zinc diethyldithiocarbamate allergenicity: potential haptenation mechanisms. Contact Dermatitis 59:79–89 178 J.-P. Lepoittevin and C. J. Le Coz

Condé-Salazar L, Del-Rio E, Guimaraens D et al Zineb is a pesticide of the dithiocarbamate (1993) Type IV allergy to rubber additives: a group. Sensitization can occur in gardeners and 10-year study of 686 cases. J Am Acad florists. Dermatol 29:176–180 Kiec-Swierczynska M (1995) Occupational sen- sitivity to rubber. Contact Dermatitis S H – 32:171 172 Zn N S Vaneckova J, Ettler K (1994) Hypersensitivity to S N

rubber surgical gloves in healthcare personnel. H – S Contact Dermatitis 31:266 267 n Von Hintzenstern J, Heese A, Koch HU et al (1991) Frequency, spectrum and occupational relevance of type IV allergies to rubber 433.1 Suggested Reading chemicals. Contact Dermatitis 24:244–252 Crippa M, Misquith L, Lonati A et al (1990) Dyshidrotic eczema and sensitization to dithio- 432 Zinc bis-Dimethyldithiocarbamate carbamates in a florist. Contact Dermatitis 23:203–204 Ziram O’Malley M, Rodriguez P, Maibach HI (1995) CAS Registry Number [137-30-4] Pesticide patch testing: California nursery Ziram is a rubber vulcanization accelerator of workers and controls. Contact Dermatitis the dithiocarbamate group. Sensitization was 32:61–62 reported in several patients. Ziram is also used as a fungicide and can cause contact dermatitis in agricultural workers. 434 Zinc Propylenebis (dithiocarbamate) SS N Zn N Propineb, Zinc N,N-Propylene-1,2-bis-dithi- S S ocarbamate CAS Registry Number [12071-83-9] Propineb is a dithiocarbamate compound, 432.1 Suggested Reading which is used as a fungicide. Sensitization was reported in agricultural workers. Kiec-Swierczynska M (1995) Occupational sen- sitivity to rubber. Contact Dermatitis S CH3 H 32:171–172 Zn N S Manuzzi P, Borrello P, Misciali C et al (1988) S N Contact dermatitis due to Ziram and Maneb. Con- H S tact Dermatitis 19:148 n

433 Zinc Ethylene-bis- 434.1 Suggested Reading dithiocarbamate Nishioka K, Takahata H (2000) Contact allergy Zineb, Zinc N,N-Ethylene-bis-dithiocarbamate due to propineb. Contact Dermatitis 43:310 CAS Registry Number [12122-67-7]