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381

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a activated zirconium aluminium glycine absolute alcohol 90 (AZAG) complex 199 absolute zero of temperature 133, acyclic monoterpenoids 273 135 acylium 149 absorption spectrum 113, 116, 117, (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, 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 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

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α‐carotene 277 androstenone 281 α‐helix 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/ 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 , 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 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

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in consumer goods 199–200 butylated hydroxytoluene (BHT) 185, BASF route, to l‐ 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, 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, 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‐ 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 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

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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 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

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reductants in 202–204 1,3‐diaminopropane 79 surfactants in 204–205 diamond crystal structure 70 coordination number, of a metal dicyclopentadiene (DCPD) 315 205 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 (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 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, 111, 116, 165, density 41, 84, 108, 109, 239 223 deodorancy 321 empyreumatic distillation 90 deterpenation 92, 268 emulsions 79–81, 84, 204, 205 8, 120 enamines 54–55, 160–161, 200, 201, deuterochloroform (CDCl3) 122, 128 348 dextrorotatory (d‐) 34, 35, 274 enantiomeric molecules 33 D‐ see dextrorotatory endothermic reactions 139 (D‐) end point of the titration 110

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9, 11, 32, 73, 91, 95, 113, 114, ethylene glycol distearate (EGDS) 78 116–120, 123, 128, 133–135, ethylene oxide 61, 77, 306 138–140, 206, 207, 219, 236, ethyne 26 350–351 eugenol 340 energy of activation 138–140, 181 carbon DEPT spectrum 130 enfleurage 2, 92, 94 1H NMR spectrum 128 enolate anion 142, 155, 156, 262, 263 infrared spectrum 128 enthalpy 134, 135, 138 mass spectrum 131 entropy 134–135, 137, 139, 149, 230, proton NMR spectrum 129 318 spectroscopic technique 127 environmental impact, of fragrance ultraviolet spectrum 129 ingredients 342–344 exothermic reaction 139 enzymes 140, 199, 211, 213, 228, 230, eye irritants 234 245, 247, 258–261, 345–347, 352, 354 f epoxide 61, 180, 297, 317 farnesene 103 Eschenmoser fragmentation 318 fatty acids 223–224 essential oils 36, 44, 59, 90–92, 95, calcium salts of 76 100–102, 104, 108, 109, 111, 112, fine fragrance 43, 90, 152, 163, 190, 127, 131–133, 160, 187, 190, 209, 194, 195, 209, 283, 284 233, 261, 268, 273–275, 283, 291, first law of thermodynamics 133 301, 310, 322, 341 Fixolide 316, 317 ester hydrolysis 137, 154–155, 162, flame ionisation detector 258 (FID) 101–102 esterification 75, 94, 137, 138, flashpoint 109 154–155, 162, 300, 311, 318 florentine 91 esters fluorine 10, 11, 148 carboxylic 49 fractionating still 88, 89 in perfumery 50 fragment based method 235 49 fragrance companies sulfate 49 commercial feasibility 337 value 111–112 ethical issue management 335–336 ethane 17–19, 177, 302 safety testing 237, 238 1,2‐ethanediol 52 fragrance industry 29, 39, 59, 81, 93, ethanol 2, 41, 49, 73, 74, 90, 94, 95, 94, 96, 107, 113, 172, 175, 230, 111, 121–123, 125, 126, 158, 194, 232, 234, 235, 238, 243, 279, 283, 209, 295 285, 286, 291, 302, 305, 307, 311, ethanolamine 199, 200 313, 325, 329, 330, 335–338, 341, ethanol‐insoluble materials 94 350 ethers 44–45, 58, 180, 183 fragrance ingredients 66 ethoxylation 77 from α‐pinene 296–299 ethyl acetate formation 49, 90 from β‐pinene 296–299 ethyl alcohol 41, 93, 305 categories 287 ethylene brassylate 49, 288, 289, 318 from cedarwood oil 300–301 ethylenediaminetetra‐acetic acid from citrus oil components 299 (EDTA) 205 development costs 285 ethylene epoxide 61 cycle 285

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from longifolene 300 geometric isomers 22–25, 312, 349 manufacture, economics geraniol 43, 231, 257, 272, 273, 283, of 284–287 291, 292, 296, 298 from petrochemicals 302–320 geranium‐scented diphenyl ether 44 raw materials for 288 Gibbs equation 135 requirements of 320–322 Gibbs’ free energy 135 fragrance oils 109, 209, 342 global toggle switch 248, 249 fragrant aldehyde 55 globular 228, 258 frankincense 284, 355 Franklin acids and bases 149 aldehyde function of 220 free energy 135 representation of 219 free radical 22, 141, 176, 181 formation from 220, 221 chain reactions 182 glycerol 75, 78, 159, 205, 224, 288 Friedel–Crafts acetylation of glycerol monostearate (GMS) 78, 205 anisole 169 glycidates 61 Friedel–Crafts acylation reaction 167, glycolysis 261 168 glycosides 220 Friedel–Crafts alkylation Google Scholar 333 reaction 167 graphite 17, 70, 71 Friedel–Crafts reaction 149, 167–168, Grignard reaction 165–167 305 gum turpentine 296, 341, 350 representation of 219 h sucrose formation from 220, 221 halogens 5, 104, 168 functional groups 40 haptens 232, 233 carbon‐nitrogen single bonds 65 HAZOP studies 322 carbon‐oxygen double bonds 63 height equivalent per theoretical plate carbon‐oxygen single bonds 63 (HETP) 88 divalent sulfur 64 Helional 55 hexavalent sulfur 64 Helvetolide 317, 318 other nitrogen 65 hemiacetals 50–51 oxygen‐oxygen single bonds 64 hemiketals 50–51 tetravalent sulfur 64 Herboxane 51 heteroatoms g acid anhydrides 50 Galaxolide 317, 343 acid chloride 50 γ‐lactones 50 alcohols 40–43 γ‐undecalactone 50 aldehydes 45–46 gas chromatography (GC) 96, 100 esters 49–50 chromatogram, of lavender oil 103 ethers 44–45 detectors 104 hydrogen bonding 39 GC‐sniffing 102 ketones 46–47 temperature ramping 101 peroxy compounds 52 gas chromatography with mass phenols 43–44 spectrometry (GC‐MS) 102, heterocyclic compounds 60–66 124, 127 hexane 21, 73, 94, 95 gas/liquid chromatography (GLC) 96 hexavalent sulfur 60, 64

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high performance liquid chromatography indole 63, 210, 211, 255, 256, 266, 279, (HPLC) 96, 100 280, 364 257, 264 inductive effect 142, 153, 178 lymphocyte test 234 inert gas‐like electron shells 12 human olfaction, organs used infrared (IR) spectroscopy 107, in 244–246 118–120 human olfactory receptor database inherently biodegradable (HORDE) 250 substance 235 hybridisation, of orbitals 11–12 intensity, odour 193, 320 hydrocarbons 15 International Fragrance Association alkynes 26 (IFRA) standard 238, 239 aromatic rings 31–33 International Union of Pure and cyclic structure 26–28 Applied Chemists (IUPAC) 24, greek leters 30–31 42 polycyclic structures 28–29 ion channels 227, 249 rules for isomers 37 ionic bonds 12, 13 rules for nomenclature 36–37 ionic compounds 13 33–36 ionic liquids 95 stereoisomers 37 ionising radiation 114 hydrodiffusion 91 ionones 277, 278, 296, 298, 305 hydroformylation 302, 303 ions and radicals formation 142 hydrogen bonding 39–41, 216 from methane 141 in acetic acid 217 irones 279 between acetic acid molecules 217 iron, oxidation and reduction of 172 between alcohol molecules 216 iso‐butane 20 in methanol 41 iso‐butene/iso‐butylene 24 between methanol and benzene 217 isobutylene 24, 144, 296, 303, 304, in water 216 311 hydrogen chloride 147, 149–151, 174, isolongifolanone 300 298 isomeric butanes 19 hydrogen fluoride 149 isomeric butenes 23–24 hydrogen molecule formation 17, 18 isomeric 6‐dodecenes 24 hydrophilic 16, 75, 77, 78, 81, 82, 218 isomerism 20, 33 hydrophobic isopentenyl pyrophosphate 270, 272 bonding 217–218 iso‐propyl,‐CH(CH3)2 22 water‐hating 75 isopropyl myristate (IPM) 78 hydroxide 153 isotopes 8 hydroxylamine (NH2OH) 112, 161 hydroxyl (‐OH) group 41 k hyperconjugation 142, 143 Karanal 159 hyphenated technique 108 Karl Fischer method 113 Hypo‐Lem 57 Kelvin scale 135 ketals 50–52, 61, 62, 158–159, 178 i ketones 46–47, 54, 112, 128, 142, 159, i‐butane 20 169, 177, 178, 180, 183, 199–201, imines (Schiff’s bases) 54, 55 203, 208, 233, 310, 368 incensole acetate 355–356 kitchen malodours 279, 280

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l m lactone 49, 50, 177, 279, 314, 318 machine dishwashing powders and laevorotatory (l‐) 34 gels 213 latent heat of fusion 73 macrocyclic musks 28, 288, 317–319, latent heat of vaporisation 73, 91 343, 345 laundry powders 133, 152, 154, 158, magnesium cation 13 170, 179, 192, 202, 211, 212, 352 magnetic nuclei 120 Laureth‐2 77 malodour management 353, 354 lavandulyl acetate 103 malodours 39, 59, 171, 173, 174, 202, l‐carvone 274 264, 279–281, 322 LD50 231, 232 mammalian wall 79, 83, 84, 226 lecithins 79, 83, 224 mass spectrometry (MS) 102, 107, Lewis acids 147–149, 167, 300 114, 124–125, 127 Lewis base 148 basic elements 125 Ligustral 45, 55, 144, 159, 305 ethanol 126 limonene 34 fragmentation 126 enantiomers of 35 ions fragment 125 linalool 103, 131, 132, 144, 231, 273, 285, matter 1–16, 67–84, 134 291, 292, 294, 296, 297, 333, 340 medium rings 28 linear alkyl‐benzene sulfonates Mefrosol 191, 308, 309 (LAS) 77 melting point 108 199, 213 Mentha arvensis 346 lipids 75 menthol 35 fatty acids 223 sustainability in living 224 energy 350–351 phospholipids 224, 225 environmental implications 350 sphingolipids 224, 225 feedstocks 349–350 triglycerides 224 meso‐ 36 lipocalins 226, 230, 246 metallurgy 1 lipophilic (oil‐loving) 75 methane 14–15, 18 liquid bleach 109, 201, 213 methanesulfonic acid 60 liquid splitter 89 methane thiol 58 lithium 4, 10, 11 methanol 40, 41, 69, 216, 217, 263, lithium fluoride (LiF) 11 295, 315 lithium oxide (Li2O) 11 (Z)‐3‐methoxy‐4‐methylhept‐3‐ene 25 l‐limonene 34 methyl anthranilate 39, 54, 55, 114, l‐menthol 274, 319 160, 161, 266, 351, 352 BASF route 349 methyl carbanion 141 from Mentha arvensis 346 methyl dihydrojasmonate 194, 314 structure 346 methyl ethyl 2‐hydroxyethyl salts 95 sustainability 345 2‐methyl‐2‐(1´ethylprop‐1‐yl) Symrise route 347 propan‐1,3‐diol 159 Takasago route 347–348 methylheptenone 166, 293–295 l‐menthyl benzoate 94 3‐methyl‐2‐hexenoic acid 280 log P 15, 16, 75, 191, 211, 233, 239, methyl iso‐amyl ketone 47 246, 324 methyl jasmonate 49, 264, 324, 327 lutensols 78 methyl ketones 47, 178, 179, 201, 283

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4(R)‐(+)‐1‐methyl‐4‐(1´‐methylethenyl) nicotinamide dinucleotide cyclohex‐1‐ene 24 phosphate (NADP) 229, 258, 260 2‐methylpropane 20 Nirvanolide 343 methyl radical 22, 25, 40, 126, 131, nitriles 156, 157, 161–162 see also 141 cyanide methyl vinyl ketone 233 nitrobenzene 57, 58 meting or fusion 73 nitro compounds 57 mevalonic acid 261, 270 nitrogen detection 104 micelles 81, 212 nitrogenous molecules 39 Michael acceptors 233, 235 nitromusks 316, 343 Michael reaction 164–165, 233, 314 n‐Octanol 75 molecular orbital 14, 114, 117 non‐soap detergents (NSDs) 76, 211 molecular recognition non‐superimposability chirality 217 of asymmetric carbon atoms 34 defined 215 isomer 33 electrostatic attraction 215 nootkatone 127, 300, 345 hydrogen bonding 216–217 normal butane/n‐butane 20 hydrophobic bonding 217–218 nor‐patchoulenol 43 van der Waals attraction 215 novel fragrance ingredient discovery 219–221 chemist’s role 322–323 monoterpenoid acetate 103 copying leads 324 monoterpenoid alcohol 103 high thoroughput screening 323 monoterpenoids 103, 268–270, odour character 325 272–276 performance tests 325 muguet aldehydes 306–307 random screening 323 musk ingredients 297, 343 statistical design 324 musk ketone 57, 58, 343 n‐pentane 20 mutagenic materials 234 nuclear magnetic resonance myrcene 103, 298, 347 (NMR) 108, 120–124 nucleic acids 218, 221–222 n nucleophiles 152–154 n‐alkanes, boiling points 22 in consumer goods 200–201 naphthalene 309–310 reaction, with perfume ingredients 200 numbering systems 33 nucleosides 221 naphthofuran 278, 301, 302 221, 222, 251, 259 natural chemicals, classes of 218 numerical prefixes 21, 24, 26 natural fragrance ingredients 340 estraction 95 o naturally sourced ingredients 337 ocimene 103 Nazarov reaction 318 octenylsuccinic acid (OSA) 78 n‐butane 20 odorous molecules 17, 39, 221, 245, neural pathways, in olfactory 246, 257, 336 perception 255 odour binding proteins 226, 245–247, neutralisation of sulfuric acid 354 (H2SO4) 136 odour perception 36, 245, 252–256, neutral surfacants 78 324, 353, 355 Newman projection 18 odour properties 198, 320, 323, 326

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OECD test 235 paper chromatography 96, 98 olefins 23, 24 paraffins 18 acid catalyzed addition to 163–164 para‐tertiary‐butylcyclohexanol metathesis 318 (PTBCHol) 138 olfaction 41, 353 para‐tertiary‐butylcyclohexyl acetate combinatorial nature 249–252 (PTBCHA) 138, 155 organs used in 244–246 patents 286, 322, 324, 326, 329, 330, receptor event 247–249 332 role in 243 pearlisers 207 transport to receptors 246–247 pentane 20, 26 olfactory epithelium 245, 256, 353, 354 peracetic acid 180, 202 olfactory receptor proteins 225, 227, perception of odour 252–256 247–250 perfume oligomerisation 302, 303 aldehydes and muguet notes 190 219 base notes 189–190 opacifiers 207 bloom 193–194 optical brighteners 207 detection threshold 192 optical rotation 109, 336 impact 192 orbitals ingredients 187 hybridisation of 11–12 dihydroxyacetone reaction shape of 9–10 with 208 organic compounds 17, 101, 102, 165, nucleophiles reaction with 200 172, 178, 221 middle/heart notes 189–190 organic reactions 140–145 molecules 75, 205, 208, 210, 246 organoleptic analysis 198 muguet and sandalwood notes 190 organosulfur compounds, oxidation notes, chords and discords 187 of 173 odour families 188 organs used, in olfaction 244 persistence and tenacity 191 orsellinic acid 263 physical and chemical factors 194 3‐oxapentane 44 radiance 193–194 1,3‐oxathiane 61 recognition threshold 192 oxazolidine 62 requirement of 187 oxidation and reduction (red‐ox) scent trail 194 reactions 171 stability 198, 210 chromium 171–172 top notes 188, 190 iron 171–172 types of 192 oxidative decarbonylation, of perfumery nitriles 57 aldehyde 183 pericyclic (or electrocyclic) oximes 54, 55, 112 reactions 144 oxirane 61 periodic table of elements 4, 5 oxygenated organics, oxidation levels Perkin triangle 87 of 177–178 peroxide 52, 59, 111, 176, 182, 233 oxygen bleaches 177, 179 peroxy compounds 52 peroxy , in organic p chemistry 176 palm kernel oil (PKO) 76 Persil 202 palm oil (PO) 76, 224 personalised perfumes 354

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personal wash products 211 pro‐drugs 351 phase transition 72, 73 pro‐fragrance system 351 phenols 44, 112, 310–312 proteases/peptidases 199 antiseptic 43 proteins 226 in essential oils 44 chemical communication 226 phenylacetaldehyde dimethyl acetal globular 228 (PADMA) 51, 306 lipocalins 226 phenylethanol 43, 91, 191, 266 primary structure 227 2‐phenylethanol 305, 342 secondary structure 227 pheromones 243, 257 tertiary structure 228–229 phosphate esters 49, 221 protium 8 phosphatidylcholine 83, 224 protons 7, 8, 10, 12, 13, 128, 129, phospholipids 224, 225 141, 163 phosphoric acid 49, 224, 258 PTBCHA formation and loss 155 photo‐active agents, in consumer p‐toluenesulfonic acid 60 goods 206 photosynthesis 261 q phototoxic materials 234 quality control (QC) 107, 131–132 pinane ring system 29 quantitative structure‐activity π‐electrons 32 relationships (QSAR) 324 of naphthalene 32 quaternary ammonium salts 53, 78, system of vanillin 158 79, 258 π*‐orbitals 117 quats 53, 78 plant derived feedstocks, advantage of 287 r platinum metals 5 racemate 36, 333, 347 polarising filters 33 racemic mixture 36, 94, 347 polar solvents 13, 15 radiance 193, 194, 320 polycyclic musks (PCMs) 316, 317, radioactive isotopes/radio‐isotopes 8, 343 104, 132, 261 polyketide biosynthesis 262–263 radio frequencies 107, 120 polymerisation 257, 302, 303, 318 (R)‐and (S)‐nomenclature 36 polypeptides 225, 227 raw materials, for fragrance 219, 221 ingredients 288 pomade 94, 95 reaction profiles 138–140 p‐orbitals 10 readily biodegradable substance 235 prenyl pyrophosphate 270 receptor event, olfaction 247 primary metabolites receptor odorant screening map 251 carbohydrates 218–221 reductants in, consumer goods 202–204 defined 218 reflux 88, 89 lipids 223–225 refractive index 100, 109, 131 proteins 225–230 refractometer 109 principle of chemical regular polygons 26, 27 equilibrium 137–138 Research Institute for Fragrance principle of microscopic Materials (RIFM) 238 reversibility 137–138 resinoid 95 process patent 330 resolution 36

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resonance 32 skew conformations 18 reviews and books 331 skin irritation 232, 234, 239 RIFM Expert Panel (REXPAN) 239 skin sensitisation 232–234, 239 rose alcohols 273, 291, 296 sodium bisulfite (NaHSO3) 200, 202 rule of thumb 138, 197 sodium cation 13, 67 sodium chloride 13, 208 s crystal 67, 68 saccharides 218–219, 221 crystal lattice, fragment 14 sandalwood ingredients 290, 343–344 sodium cumenesulfonate (SCS) 77 sandalwood oil 276, 340, 344 sodium hydroxide (NaOH) 75–76, 136 Santalum album 340 sodium hypochlorite 109, 174, 175, saponification 75 186, 201 saturated hydrocarbons 177 sodium ion 67, 74 saturated solution 74 sodium lauryl ether sulfate (SLES) 77 scented candles 212 sodium nonanoyloxybenzenesulfonate/ scent trail 194 percarbonate bleach Schiff’s bases 54–55, 160–161, 178, system 202 200 sodium or 75, 111 schizophrenic acid 48, 280 sodium sulfate (Na2SO4) 136 SciFinder 332, 333 soft electrophiles 153, 233, 234 sclareolide 301, 302, 344 solid shading 14, 34 secondary metabolites 218 solubility 43, 74–75, 85, 91, 93, 96, biosynthesis of 261–262 164, 234, 239 second law of thermodynamics 134 solute 74 semiochemicals 257 solvent 2, 13, 16, 69, 74 sense of smell 2, 131, 215, 243, 244, extraction 94 250, 254 soot/carbon black 69 separation and purification space‐filling model 15 crystallisation 93–94 spectrometers 113 distillation 85–93 basic components 116 azeotropes, formation of 90 spectroscopic techniques 114, 115, Dean and Stark apparatus 90 127–131 fractionating still 89 spectrum, of red dye 116–117 hydrodiffusion 91 sphingolipids 224, 225 under reduced pressure 87 sphingomyelin 83, 225 steam still 91 sp3 orbitals 11, 12, 14 natural fragrance ingredients staggered conformation 18, 28 estraction 95 standard temperature and pressure sublimation 93 (STP) 21 sesquiterpenoid hydrocarbons 103, states of matter 200 bilayers 82–84 sesquiterpenoids 103, 268, 275–276 colloids 84 shikimate raw materials, for fragrance detergency 81–82 ingredient production 288 emulsions 79–81 shikimic acid 261, 265–267 gas 71 σ*‐orbital 117 liquids 71 silicones 78, 100 micelles 81

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states of matter (contd.) neutral surfacants 78 simple phase diagram 72 sulfonic acids 77 solids two‐phase systems 73 crystalline solid 68 sustainability, in fragrance industry cubic crystal lattice 67, 68 definition 335 diamond crystal structure 70 health and wellbeing and perfume/ graphite 70 sense of smell 355–356 soot/carbon black 69 malodour management 354 surfactants, oil/water interface 76 natural fragrance stereoisomerism 33–36 ingredients 340–341 stereoisomers 34–37, 346, 349 social and health factors 353–356 steroids 95, 269, 277 synthetic ingredients 341–351 storage conditions, of perfumes 197 understanding olfaction 353–354 structure‐activity relationships Symrise route, to l‐menthol (SAR) 324 production 347 structure‐odour synperonics 77 relationship 324–325 synthetic fragrance ingredients 283 s‐type orbital 9 biotechnology 345 styrene monomer/propylene oxide environmental impact 342–344 (SMPO) process 305 factors for the use of 283 sub‐critical water 95 legal labelling requirements 284 sublimation 93 l‐menthol 345 sulfate esters 49, 59 safety 284 sulfate turpentine 290, 296, 337, 341, secure supply using chemical 342 process 284 sulfonate 59, 77 stability issues 283 sulfonic acids 59–60, 77, 169, 173 use of by‐products 341 sulfonyl chlorides 59, 60 sulfoxides 59, 173 t sulfur 3, 39, 58, 104 Takasago route, to l‐menthol 347–348 divalent sulfur compounds 58 tartaric acid 36 hexavalent 60 tautomers 54, 155, 156, 160, 208 molecule 39 temperature ramping 101 oxidation states of 172 tenacity, odour 320 oxoacids, structure of 175 terpeneless oil 92 thio‐ether 59 terpenoids 95, 267, 290 thiols or mercaptans 58 building blocks 270, 271 sulfuric acid 49, 59, 60, 98, 136, 148, defined 268 149, 173, 230, 288, 316 isoprene and head‐tail linkage super‐saturated solution 74 in 269 surface active agents 53, 75, 204 isoprene units, mechanism of surfactants 75 coupling 270, 271 anionic surfacants 77 terpineol 103, 297 cationic surfacants 79 tertiary‐butyl,‐C(CH3)3 22 in consumer goods 205 tertiary‐butyl carbocation 143 DEFI 77 tetraacetylethylenediamine (TAED) LAS 77 activators 179, 180, 202

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1,1,1,2‐tetrafluoroethane 95 u 12, 14, 17, 53, 59, 331 ultimately biodegradable tetrahydrofuran 61, 165 substance 235 tetrahydropyran 61 Ultravanil 158 tetrahydrothiophene 61 ultraviolet (UV) 100, 113–120, 206, tetramethylsilane (TMS) 121 352 thermodynamics 133–135 ultraviolet/visible (UV/Vis) 107, 113 thiazolidine 62 unit cell, of crystal 67 thin layer chromatography (TLC) 96, unwanted acetal formation 160 98–99 unwanted aldol condensations 157 thio‐ether 58, 59, 173, 174, 202 thioglycolic acid 200–204 v thiols or mercaptans 58 valence 4, 9–11, 14, 19, 56, 148, 171, thiomethanol 58 300, 345 thionyl chloride (SOCl2) 50 Van der Waals interactions 68–69 thioterpineol 59 vanillin 158, 210, 288, 311 thyme 44 vapor pressure 73 tincture 94 vapour phase chromatography titration 110–113, 198, 221 (VPC) 96 tobacco smoke malodour 280 vapour splitting device 89 tocopherol 185, 203 vegetable oils 15, 75, 199, 288 toxicology 230–231 viscosity 109 trail 194, 320 visualisation 97–99 1,3‐trans 24 vitamin B12 5 trans‐2‐butene 23 volatility, perfume ingredients 191 trans‐6‐dodecene 24 7‐transmembrane G‐protein coupled w receptors 247 Wagner–Meerwein Traseolide 149 rearrangement 273 trickle down 195 wanted acetal formation 160 triglycerides 224 wanted aldol condensations 157 trihydric alcohol glycerol 159 water (H2O) 2, 3, 13, 15, 77, 112–113, 2,6,6‐trimethylbicyclo[3.1.1]hept‐2‐ 136 ene 29 of cohobation 91 1,3,5‐trioxane 61, 159 woody odorants 247, 342, 352 triphenylmethane dyes 206 ω‐oxidation 236 triple bonds 26, 28, 56 triple point 72 x 1,2,4‐trisubstituted aromatic ring 128 xylene 32 triterpene ambreine 278 tritium 8 y trivial names 24, 32, 45, 46, 48, 57, 68 ylang‐ylang 39, 190 turpentine 28, 31, 86, 187, 238, 274, Ysamber K 52 288, 290, 291, 296, 300, 302, 326, 337, 341, 342, 350 z 2s orbital 9, 22 Zwitterionic surfactants 79, 80

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