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Absolute Alcohol 90 Absolute Zero of Temperature 133, 135 Absorption Spectrum 113, 116, 117, 119 Abstracts 331–332 Acetal Form

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Absolute Alcohol 90 Absolute Zero of Temperature 133, 135 Absorption Spectrum 113, 116, 117, 119 Abstracts 331–332 Acetal Form 381 Index a activated zirconium aluminium glycine absolute alcohol 90 (AZAG) complex 199 absolute zero of temperature 133, acyclic monoterpenoids 273 135 acylium ions 149 absorption spectrum 113, 116, 117, adenosine triphosphate (ATP) 249, 119 250, 258, 259 abstracts 331–332 adipic acid 291, 313, 342 acetal formation 159, 160 adulteration, of essential oils 336 acetals 50, 158 air fresheners 192, 194, 209, 212 formation of 159 alcohols 40–41, 43 acetonitrile 56 dehydration 162–163 acetylenes 26, 166 aldehydes 45, 112, 158–159, 177–178, acetylide anion 167 182, 183 acid anhydrides 50–51 aromatic 45 acid catalyzed addition perfumery 46 to cyclopropanes 164 aldol condensation 155–158, 263, 288, to olefins 163–164 292, 297, 309, 313, 314 acid chloride 50–51, 59, 63, 148, 167, aldol reaction 155–158, 209, 236, 263, 168 304, 365 acids 111 alicyclic aldehydes 45 and bases alicyclic materials 32 perfume ingredients stability 152 alicyclic musks 297, 317 pH 150–152 aliphatic fragrance ingredients, from strong and weak 149–150 ethylene 303 in water 150 alkanes 18, 20–23, 125 in consumer goods alkenes 22–25, 31 anhydrous aluminium alkyl ethoxylates (AEs) 77, 208 chloride 199 alkyl peroxy radical 182 calcium salts 198 alkynes 26 limescale removal/prevention 198 allelochemicals 257 pH control agents 198 allyl isothiocyanate 234 zirconium chloride 199 α,β‐unsaturated carbonyls 165 activated aluminium chlorohydrate α,β‐unsaturated ketone 156, 157 (AACH) 199 α‐carbon 142 Fundamentals of Fragrance Chemistry, First Edition. Charles S. Sell. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2019 by Wiley-VCH Verlag GmbH & Co. KGaA bindex.indd 381 2/26/2019 3:26:02 PM 382 Index α‐carotene 277 androstenone 281 α‐helix protein structure 227 aniline 149, 150, 208 α‐hydroxy amine 54 Animusk 319 α‐pinene 28–29, 86 anionic surfacants 77 α‐terpineol 43, 164 anions stabilisation, by aluminium chloride 148, 149, 167, hyperconjucation 143 199, 317 anisaldehyde 45, 46, 267, 311 ambergris 94, 189, 278, 301 anisole (methoxybenzene) 169 amboryl acetate 300 antibacterial agents, in consumer ambrofix 278, 301, 344, 345 goods 207–208 Ames test 234, 339 antimicrobial sesquiterpenoid 258 amide formation 56 antioxidants 180, 184–185 amide/peptide 55–56 antiperspirants 148, 152, 199 amines 53, 79, 160, 201, 208, 280 application patents 330 amygdalin 220 arachidonic acid 264 sources of 220 Arens–van Dorp synthesis, of structure of 220 citral 293–294 amylcinnamic aldehyde (ACA) 157, aromatic aldehydes 45 288 aromaticity 32, 62 analysis aromatic molecules, electrophilic chemical methods substitutions 168–170 acids 111 Arquad and Hamburg Ester Quat aldehyde 112 (HEQ) 78 base 111 asymmetric carbon atoms 33, 34, 219 COD 112 atom efficiency 292–295 ester value 111–112 atomic absorption 113 ketones 112 atomic number 4–8, 25, 35, 37, 61 peroxide content 111 atomic structure 7–8 phenols 112 atomic theory 1–7 titration 110 atomic weight 4–8, 292 water 112 atoms 4 physical methods electronic structure 9–11 boiling point 108 Aufbau Principle 10 colour 109 autoxidation 171, 180 density 108 of fats 184 flashpoint 109 in perfume containing an melting point 108 aldehyde 182 optical rotation 109 of pinane 296 refractive index 109 of 4‐tetrahydronapthalene 1–3, 181 viscosity 109 azeotropes, formation of 90 spectroscopic methods 113–114 azo‐dyes 206 eugenol 127–131 GC‐MS 127 b IR 118–120 Baeyer–Villiger reaction 177 NMR 120–124 Barbier–Bouveault–Tiemann synthesis, quality control 131–132 of citral 292 UV 114–118 bases 111 bindex.indd 382 2/26/2019 3:26:02 PM Index 383 in consumer goods 199–200 butylated hydroxytoluene (BHT) 185, BASF route, to l‐menthol 203 production 349 benzene 31–33, 43, 62, 69–71, 90, 95, c 162, 163, 169, 181, 201, 217, 305, calcium carbonate (CaCO3) 136, 198, 310 199 benzoic acid 49, 307, 308 calcium hydrogen carbonate/ benzophenone 46, 118 Ca(HCO3)2 136 benzylic oxidation, of calcium hydroxide 148, 198 toluene 307–308 canonical structures 32, 162, 164 bergaptene 234, 261, 338 carazolol 248 beryllium fluoride (BeF2) 11 carbanions 141, 142, 164, 180 beryllium oxide (BeO) 11 carbocations 141, 162 β‐oxidation pathway 342–343 formation 143 bilayers 82–84 stabilisation, by conjucation 143 biodegradability 211, 235, 237–239, carbohydrates 78, 82, 218–221 317, 339, 342, 343 carbon 3, 8, 10–12, 14, 15, 17–66, 69, biological oxygen demand (BOD) 112 119, 121, 124, 126, 130, 132, 134, biosynthesis 140–142, 153, 155, 160, 162, of carotenoids 276 164–166, 177, 178, 180, 182, 191, enzymes and cofactors 258–261 223, 236, 246, 288 of fatty acids 223 carbon dating 8, 132 of jasminic acid derivatives 264 carbonic acid (H2CO3) 136, 151 polyketide 262–263 carbon‐magnesium bond 166 principles of 258–261 carbon orbitals 15 of secondary metabolites 261–262 carbon‐oxygen bond 40, 142, 144, 159, Biradex N 68–69 272 crystal packing 70 carbonyl carbon 45–47, 54, 142, 153, one molecule of 69 154, 156, 160, 164, 178, 182, 200, structure of 69 259 bloom 193–194, 320 carbonyl compounds 51, 62, 155, 156, boiling point 21, 22, 29, 36, 72, 85, 86, 158, 164, 166, 203 88–91, 100, 101, 108, 138, 216, carboxaldehyde 45 234, 239, 324, 349 carboxylic acid chlorides 59 borneol 103, 290 carboxylic acids 39, 47–50, 55, 59, 77, boron trifluoride 148, 167 94, 95, 137, 154, 169, 178, 199, Bourgeonal 45 205, 225, 236, 247, 259, 288, 303, brassylic acid 49, 288 313–315, 318, 342, 366 Brønsted acids 147, 148, 167, 168, 301 carboxylic ester 49, 61, 77 Brønsted base 150 carene 341 burette 110 carotenoids 269, 277–279 “burning” of TNT vs. burning of Carroll reaction, in citral synthesis 294 coal 140 caryophyllene 28, 29, 103, 269 butene 23, 24 catalysts 5, 60, 113, 140, 167, 199, 213, butenolides 50 225, 228, 258, 295, 348, 349 butylated hydroxyanisole (BHA) 185, cationic surfactants 78, 79 203 C–C double bond formation 23 bindex.indd 383 2/26/2019 3:26:02 PM 384 Index C–C σ bond 23 cis‐2‐butene 23 C–C triple bond formation 26 cis‐6‐dodecene 24 ceramide‐derived lipid 83 5‐cis‐undecatriene 24 chalcones 68 citation index 332 Chanel No 5 45, 188–190, 192 citral 291, 340, 349 character, odour 320 Arens–van Dorp concept 293–294 chelating agents, in consumer Barbier–Bouveault–Tiemann goods 205–206 synthesis route 292 chemical abstracts (CAS) Carroll reaction 293–294 numbers 332 Claisen rearrangement 295 chemical bonding 10, 12–16, 215 from isobutylene 296 chemical information 333 citric acid 205 chemical issues, patents 330 citronellol 43, 191, 231, 273, 290–292, chemical oxygen demand (COD) 112, 298 178 citronellonitrile 57 chemical reactions 73, 112, 114, 133, citronellyl nitrile 57 135–137, 141, 197, 228, 257, citrus oils 24, 34, 127, 274, 284, 285, 301 298, 299 chemical shift 121–124 Claisen rearrangement, in citral chemoreception 215, 243 synthesis 295 chemotaxonomy 262 clog P values 75 chirality 33, 109, 217, 299, 300, 346, 13C NMR spectra 124 348 C=O bond 45 chiral molecules 33 cocamido propyl betaine (CAPB) 79 chlorine coenzyme‐A (CoA) 259, 260 oxidation states of 174 cofactors 258–261 oxoacids, structure of 175 colloids 84 chloroform reaction 122, 128, 178, column chromatography 96, 99, 100 179, 201 common salt 5, 13, 67 chlorophyll 95 concretes 2, 95 C6H5NH2 149 conformational isomers 17–19 CHO (carbon, hydrogen, oxygen) conformers 19 compounds 39 constant boiling mixture 90 chromatography 95 consumer goods column 99 acids in 198–199 gas 100–104 antibacterial agents in 207–208 HPLC 100 bases in 199–200 mobile phase 96 chelating agents in 205–206 paper 98 cosmetics and toiletries 210 principles of 96, 97 fine fragrance 209 stationary phase 96 household products 212–214 thin layer 98–99 laundry powders 211–212 types 96 malodours in 279–281 visualisation technique 98 nucleophiles in 200–201 chromium, red‐ox cycle of 171–172 personal wash category 210–211 cineole 341 photo‐active agents in 206–207 cinnamic acid 49 reactive ingredients in 208 bindex.indd 384 2/26/2019 3:26:02 PM Index 385 reductants in 202–204 1,3‐diaminopropane 79 surfactants in 204–205 diamond crystal structure 70 coordination number, of a metal dicyclopentadiene (DCPD) 315 ion 205 Diels–Alder reaction 144, 145, 298, 13C or carbon 13 8, 120, 123, 126, 130, 305, 315 132 diethyl ether 44, 165 14C or carbon 14 8, 132, 261 digitalis 231 cosmic radiation 132 dihydroeugenol 341 coupling constant 123 dihydromyrcenol 43, 296, 297 covalent bonds 12 dihydroxyacetone (DHA) reaction, with formation of perfume ingredients 208 b/w two hydrogen atoms 14 dimethylbenzene 32 in methane 15 dimethyl sulfoxide (DMSO) 59 critical point 72 diols 41, 51, 159 critical pressure 72 1,3‐dioxan 61 critical temperature 72, 95 1,3‐dioxolane 61 crude sulfate turpentine (CST) 296, distillate 2, 85–88 350 distortionless enhancement by crystallisation 74, 85, 93–94, 248, 346, polarisation transfer 347 (DEPT) 123 cubic crystal lattice 67 disulfides 59, 203, 204, 226–228 cyanide 56, 57, 230 d‐limonene 34 cyclic monoterpenoids 103, 273, 274 cyclobutane 27, 144 e cyclohexane conformation 27 E‐and Z‐geometric isomers 35 cyclopentadecanolide 318, 343 eclipsed conformation 18 cyclopentadiene 315 ecotoxicity 232, 235 cyclopentane 26, 27, 315 Efetaal 51 cyclopropane 27, 164 electromagnetic radiation 107, 113, Cytochrome P450 5, 245, 247 206 electromagnetic spectrum 113, 114 d 2‐electron bonds 18 damascones 277, 278 electronic structure Darzens reaction 61 atoms 9–11 Dean and Stark apparatus 90 transition metals 11 decanoic acid 79 electrophiles 147, 152–154, 167–169, decanonitrile 57 233, 234 defence chemicals 257 electrostatic forces 67, 215 denaturing 228 elements 2–11, 17, 39,
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