381

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

aabsolute alcohol 90absolute zero of temperature 133,

135absorption spectrum 113, 116, 117,

119abstracts 331–332acetal formation 159, 160acetals 50, 158

formation of 159acetonitrile 56acetylenes 26, 166acetylide anion 167acid anhydrides 50–51acid catalyzed addition

to cyclopropanes 164to olefins 163–164

acid chloride 50–51, 59, 63, 148, 167, 168

acids 111and bases

perfume ingredients stability 152pH 150–152strong and weak 149–150in water 150

in consumer goodsanhydrous aluminium

chloride 199calcium salts 198limescale removal/prevention 198pH control agents 198zirconium chloride 199

activated aluminium chlorohydrate (AACH) 199

activated zirconium aluminium glycine (AZAG) complex 199

acyclic monoterpenoids 273acylium ions 149adenosine triphosphate (ATP) 249,

250, 258, 259adipic acid 291, 313, 342adulteration, of essential oils 336air fresheners 192, 194, 209, 212alcohols 40–41, 43

dehydration 162–163aldehydes 45, 112, 158–159, 177–178,

182, 183aromatic 45perfumery 46

aldol condensation 155–158, 263, 288, 292, 297, 309, 313, 314

aldol reaction 155–158, 209, 236, 263, 304, 365

alicyclic aldehydes 45alicyclic materials 32alicyclic musks 297, 317aliphatic fragrance ingredients, from

ethylene 303alkanes 18, 20–23, 125alkenes 22–25, 31alkyl ethoxylates (AEs) 77, 208alkyl peroxy radical 182alkynes 26allelochemicals 257allyl isothiocyanate 234α,β‐unsaturated carbonyls 165α,β‐unsaturated ketone 156, 157α‐carbon 142

Index

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Index382

α‐carotene 277α‐helix protein structure 227α‐hydroxy amine 54α‐pinene 28–29, 86α‐terpineol 43, 164aluminium chloride 148, 149, 167,

199, 317ambergris 94, 189, 278, 301amboryl acetate 300ambrofix 278, 301, 344, 345Ames test 234, 339amide formation 56amide/peptide 55–56amines 53, 79, 160, 201, 208, 280amygdalin 220

sources of 220structure of 220

amylcinnamic aldehyde (ACA) 157, 288

analysischemical methods

acids 111aldehyde 112base 111COD 112ester value 111–112ketones 112peroxide content 111phenols 112titration 110water 112

physical methodsboiling point 108colour 109density 108flashpoint 109melting point 108optical rotation 109refractive index 109viscosity 109

spectroscopic methods 113–114eugenol 127–131GC‐MS 127IR 118–120NMR 120–124quality control 131–132UV 114–118

androstenone 281aniline 149, 150, 208Animusk 319anionic surfacants 77anions stabilisation, by

hyperconjucation 143anisaldehyde 45, 46, 267, 311anisole (methoxybenzene) 169antibacterial agents, in consumer

goods 207–208antimicrobial sesquiterpenoid 258antioxidants 180, 184–185antiperspirants 148, 152, 199application patents 330arachidonic acid 264Arens–van Dorp synthesis, of

citral 293–294aromatic aldehydes 45aromaticity 32, 62aromatic molecules, electrophilic

substitutions 168–170Arquad and Hamburg Ester Quat

(HEQ) 78asymmetric carbon atoms 33, 34, 219atom efficiency 292–295atomic absorption 113atomic number 4–8, 25, 35, 37, 61atomic structure 7–8atomic theory 1–7atomic weight 4–8, 292atoms 4

electronic structure 9–11Aufbau Principle 10autoxidation 171, 180

of fats 184in perfume containing an

aldehyde 182of pinane 296of 4‐tetrahydronapthalene 1–3, 181

azeotropes, formation of 90azo‐dyes 206

bBaeyer–Villiger reaction 177Barbier–Bouveault–Tiemann synthesis,

of citral 292bases 111

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Index 383

in consumer goods 199–200BASF route, to l‐menthol

production 349benzene 31–33, 43, 62, 69–71, 90, 95,

162, 163, 169, 181, 201, 217, 305, 310

benzoic acid 49, 307, 308benzophenone 46, 118benzylic oxidation, of

toluene 307–308bergaptene 234, 261, 338beryllium fluoride (BeF2) 11beryllium oxide (BeO) 11β‐oxidation pathway 342–343bilayers 82–84biodegradability 211, 235, 237–239,

317, 339, 342, 343biological oxygen demand (BOD) 112biosynthesis

of carotenoids 276enzymes and cofactors 258–261of fatty acids 223of jasminic acid derivatives 264polyketide 262–263principles of 258–261of secondary metabolites 261–262

Biradex N 68–69crystal packing 70one molecule of 69structure of 69

bloom 193–194, 320boiling point 21, 22, 29, 36, 72, 85, 86,

88–91, 100, 101, 108, 138, 216, 234, 239, 324, 349

borneol 103, 290boron trifluoride 148, 167Bourgeonal 45brassylic acid 49, 288Brønsted acids 147, 148, 167, 168, 301Brønsted base 150burette 110“burning” of TNT vs. burning of

coal 140butene 23, 24butenolides 50butylated hydroxyanisole (BHA) 185,

203

butylated hydroxytoluene (BHT) 185, 203

ccalcium carbonate (CaCO3) 136, 198,

199calcium hydrogen carbonate/

Ca(HCO3)2 136calcium hydroxide 148, 198canonical structures 32, 162, 164carazolol 248carbanions 141, 142, 164, 180carbocations 141, 162

formation 143stabilisation, by conjucation 143

carbohydrates 78, 82, 218–221carbon 3, 8, 10–12, 14, 15, 17–66, 69,

119, 121, 124, 126, 130, 132, 134, 140–142, 153, 155, 160, 162, 164–166, 177, 178, 180, 182, 191, 223, 236, 246, 288

carbon dating 8, 132carbonic acid (H2CO3) 136, 151carbon‐magnesium bond 166carbon orbitals 15carbon‐oxygen bond 40, 142, 144, 159,

272carbonyl carbon 45–47, 54, 142, 153,

154, 156, 160, 164, 178, 182, 200, 259

carbonyl compounds 51, 62, 155, 156, 158, 164, 166, 203

carboxaldehyde 45carboxylic acid chlorides 59carboxylic acids 39, 47–50, 55, 59, 77,

94, 95, 137, 154, 169, 178, 199, 205, 225, 236, 247, 259, 288, 303, 313–315, 318, 342, 366

carboxylic ester 49, 61, 77carene 341carotenoids 269, 277–279Carroll reaction, in citral synthesis 294caryophyllene 28, 29, 103, 269catalysts 5, 60, 113, 140, 167, 199, 213,

225, 228, 258, 295, 348, 349cationic surfactants 78, 79C–C double bond formation 23

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Index384

C–C σ bond 23C–C triple bond formation 26ceramide‐derived lipid 83chalcones 68Chanel No 5 45, 188–190, 192character, odour 320chelating agents, in consumer

goods 205–206chemical abstracts (CAS)

numbers 332chemical bonding 10, 12–16, 215chemical information 333chemical issues, patents 330chemical oxygen demand (COD) 112,

178chemical reactions 73, 112, 114, 133,

135–137, 141, 197, 228, 257, 301

chemical shift 121–124chemoreception 215, 243chemotaxonomy 262chirality 33, 109, 217, 299, 300, 346,

348chiral molecules 33chlorine

oxidation states of 174oxoacids, structure of 175

chloroform reaction 122, 128, 178, 179, 201

chlorophyll 95C6H5NH2 149CHO (carbon, hydrogen, oxygen)

compounds 39chromatography 95

column 99gas 100–104HPLC 100mobile phase 96paper 98principles of 96, 97stationary phase 96thin layer 98–99types 96visualisation technique 98

chromium, red‐ox cycle of 171–172cineole 341cinnamic acid 49

cis‐2‐butene 23cis‐6‐dodecene 245‐cis‐undecatriene 24citation index 332citral 291, 340, 349

Arens–van Dorp concept 293–294Barbier–Bouveault–Tiemann

synthesis route 292Carroll reaction 293–294Claisen rearrangement 295from isobutylene 296

citric acid 205citronellol 43, 191, 231, 273, 290–292,

298citronellonitrile 57citronellyl nitrile 57citrus oils 24, 34, 127, 274, 284, 285,

298, 299Claisen rearrangement, in citral

synthesis 295clog P values 7513C NMR spectra 124C=O bond 45cocamido propyl betaine (CAPB) 79coenzyme‐A (CoA) 259, 260cofactors 258–261colloids 84column chromatography 96, 99, 100common salt 5, 13, 67concretes 2, 95conformational isomers 17–19conformers 19constant boiling mixture 90consumer goods

acids in 198–199antibacterial agents in 207–208bases in 199–200chelating agents in 205–206cosmetics and toiletries 210fine fragrance 209household products 212–214laundry powders 211–212malodours in 279–281nucleophiles in 200–201personal wash category 210–211photo‐active agents in 206–207reactive ingredients in 208

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Index 385

reductants in 202–204surfactants in 204–205

coordination number, of a metal ion 205

13C or carbon 13 8, 120, 123, 126, 130, 132

14C or carbon 14 8, 132, 261cosmic radiation 132coupling constant 123covalent bonds 12

formation ofb/w two hydrogen atoms 14in methane 15

critical point 72critical pressure 72critical temperature 72, 95crude sulfate turpentine (CST) 296,

350crystallisation 74, 85, 93–94, 248, 346,

347cubic crystal lattice 67cyanide 56, 57, 230cyclic monoterpenoids 103, 273, 274cyclobutane 27, 144cyclohexane conformation 27cyclopentadecanolide 318, 343cyclopentadiene 315cyclopentane 26, 27, 315cyclopropane 27, 164Cytochrome P450 5, 245, 247

ddamascones 277, 278Darzens reaction 61Dean and Stark apparatus 90decanoic acid 79decanonitrile 57defence chemicals 257denaturing 228density 41, 84, 108, 109, 239deodorancy 321deterpenation 92, 268deuterium 8, 120deuterochloroform (CDCl3) 122, 128dextrorotatory (d‐) 34, 35, 274D‐glyceraldehyde see dextrorotatory

(D‐)

1,3‐diaminopropane 79diamond crystal structure 70dicyclopentadiene (DCPD) 315Diels–Alder reaction 144, 145, 298,

305, 315diethyl ether 44, 165digitalis 231dihydroeugenol 341dihydromyrcenol 43, 296, 297dihydroxyacetone (DHA) reaction, with

perfume ingredients 208dimethylbenzene 32dimethyl sulfoxide (DMSO) 59diols 41, 51, 1591,3‐dioxan 611,3‐dioxolane 61distillate 2, 85–88distortionless enhancement by

polarisation transfer (DEPT) 123

disulfides 59, 203, 204, 226–228d‐limonene 34

eE‐and Z‐geometric isomers 35eclipsed conformation 18ecotoxicity 232, 235Efetaal 51electromagnetic radiation 107, 113,

206electromagnetic spectrum 113, 1142‐electron bonds 18electronic structure

atoms 9–11transition metals 11

electrophiles 147, 152–154, 167–169, 233, 234

electrostatic forces 67, 215elements 2–11, 17, 39, 111, 116, 165,

223empyreumatic distillation 90emulsions 79–81, 84, 204, 205enamines 54–55, 160–161, 200, 201,

348enantiomeric molecules 33endothermic reactions 139end point of the titration 110

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Index386

energy 9, 11, 32, 73, 91, 95, 113, 114, 116–120, 123, 128, 133–135, 138–140, 206, 207, 219, 236, 350–351

energy of activation 138–140, 181enfleurage 2, 92, 94enolate anion 142, 155, 156, 262, 263enthalpy 134, 135, 138entropy 134–135, 137, 139, 149, 230,

318environmental impact, of fragrance

ingredients 342–344enzymes 140, 199, 211, 213, 228, 230,

245, 247, 258–261, 345–347, 352, 354

epoxide 61, 180, 297, 317Eschenmoser fragmentation 318essential oils 36, 44, 59, 90–92, 95,

100–102, 104, 108, 109, 111, 112, 127, 131–133, 160, 187, 190, 209, 233, 261, 268, 273–275, 283, 291, 301, 310, 322, 341

ester hydrolysis 137, 154–155, 162, 258

esterification 75, 94, 137, 138, 154–155, 162, 300, 311, 318

esterscarboxylic 49in perfumery 50phosphate 49sulfate 49value 111–112

ethane 17–19, 177, 3021,2‐ethanediol 52ethanol 2, 41, 49, 73, 74, 90, 94, 95,

111, 121–123, 125, 126, 158, 194, 209, 295

ethanolamine 199, 200ethanol‐insoluble materials 94ethers 44–45, 58, 180, 183ethoxylation 77ethyl acetate formation 49, 90ethyl alcohol 41, 93, 305ethylene brassylate 49, 288, 289, 318ethylenediaminetetra‐acetic acid

(EDTA) 205ethylene epoxide 61

ethylene glycol distearate (EGDS) 78ethylene oxide 61, 77, 306ethyne 26eugenol 340

carbon DEPT spectrum 1301H NMR spectrum 128infrared spectrum 128mass spectrum 131proton NMR spectrum 129spectroscopic technique 127ultraviolet spectrum 129

exothermic reaction 139eye irritants 234

ffarnesene 103fatty acids 223–224

calcium salts of 76fine fragrance 43, 90, 152, 163, 190,

194, 195, 209, 283, 284first law of thermodynamics 133Fixolide 316, 317flame ionisation detector

(FID) 101–102flashpoint 109florentine 91fluorine 10, 11, 148fractionating still 88, 89fragment based method 235fragrance companies

commercial feasibility 337ethical issue management 335–336safety testing 237, 238

fragrance industry 29, 39, 59, 81, 93, 94, 96, 107, 113, 172, 175, 230, 232, 234, 235, 238, 243, 279, 283, 285, 286, 291, 302, 305, 307, 311, 313, 325, 329, 330, 335–338, 341, 350

fragrance ingredients 66from α‐pinene 296–299from β‐pinene 296–299categories 287from cedarwood oil 300–301from citrus oil components 299development costs 285life cycle 285

bindex.indd 386 2/26/2019 3:26:02 PM

Index 387

from longifolene 300manufacture, economics

of 284–287from petrochemicals 302–320raw materials for 288requirements of 320–322

fragrance oils 109, 209, 342fragrant aldehyde 55frankincense 284, 355Franklin acids and bases 149free energy 135free radical 22, 141, 176, 181

chain reactions 182Friedel–Crafts acetylation of

anisole 169Friedel–Crafts acylation reaction 167,

168Friedel–Crafts alkylation

reaction 167Friedel–Crafts reaction 149, 167–168,

305fructose

representation of 219sucrose formation from 220, 221

functional groups 40carbon‐nitrogen single bonds 65carbon‐oxygen double bonds 63carbon‐oxygen single bonds 63divalent sulfur 64hexavalent sulfur 64other nitrogen 65oxygen‐oxygen single bonds 64tetravalent sulfur 64

gGalaxolide 317, 343γ‐lactones 50γ‐undecalactone 50gas chromatography (GC) 96, 100

chromatogram, of lavender oil 103detectors 104GC‐sniffing 102temperature ramping 101

gas chromatography with mass spectrometry (GC‐MS) 102, 124, 127

gas/liquid chromatography (GLC) 96

geometric isomers 22–25, 312, 349geraniol 43, 231, 257, 272, 273, 283,

291, 292, 296, 298geranium‐scented diphenyl ether 44Gibbs equation 135Gibbs’ free energy 135global toggle switch 248, 249globular proteins 228, 258glucose

aldehyde function of 220representation of 219sucrose formation from 220, 221

glycerol 75, 78, 159, 205, 224, 288glycerol monostearate (GMS) 78, 205glycidates 61glycolysis 261glycosides 220Google Scholar 333graphite 17, 70, 71Grignard reaction 165–167gum turpentine 296, 341, 350

hhalogens 5, 104, 168haptens 232, 233HAZOP studies 322height equivalent per theoretical plate

(HETP) 88Helional 55Helvetolide 317, 318hemiacetals 50–51hemiketals 50–51Herboxane 51heteroatoms

acid anhydrides 50acid chloride 50alcohols 40–43aldehydes 45–46esters 49–50ethers 44–45hydrogen bonding 39ketones 46–47peroxy compounds 52phenols 43–44

heterocyclic compounds 60–66hexane 21, 73, 94, 95hexavalent sulfur 60, 64

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Index388

high performance liquid chromatography (HPLC) 96, 100

hormones 257, 264human lymphocyte test 234human olfaction, organs used

in 244–246human olfactory receptor database

(HORDE) 250hybridisation, of orbitals 11–12hydrocarbons 15

alkynes 26aromatic rings 31–33cyclic structure 26–28greek leters 30–31polycyclic structures 28–29rules for isomers 37rules for nomenclature 36–37stereoisomerism 33–36stereoisomers 37

hydrodiffusion 91hydroformylation 302, 303hydrogen bonding 39–41, 216

in acetic acid 217between acetic acid molecules 217between alcohol molecules 216in methanol 41between methanol and benzene 217in water 216

hydrogen chloride 147, 149–151, 174, 298

hydrogen fluoride 149hydrogen molecule formation 17, 18hydrophilic 16, 75, 77, 78, 81, 82, 218hydrophobic

bonding 217–218water‐hating 75

hydroxide 153hydroxylamine (NH2OH) 112, 161hydroxyl (‐OH) group 41hyperconjugation 142, 143hyphenated technique 108Hypo‐Lem 57

ii‐butane 20imines (Schiff ’s bases) 54, 55incensole acetate 355–356

indole 63, 210, 211, 255, 256, 266, 279, 280, 364

inductive effect 142, 153, 178inert gas‐like electron shells 12infrared (IR) spectroscopy 107,

118–120inherently biodegradable

substance 235intensity, odour 193, 320International Fragrance Association

(IFRA) standard 238, 239International Union of Pure and

Applied Chemists (IUPAC) 24, 42

ion channels 227, 249ionic bonds 12, 13ionic compounds 13ionic liquids 95ionising radiation 114ionones 277, 278, 296, 298, 305ions and radicals formation 142

from methane 141irones 279iron, oxidation and reduction of 172iso‐butane 20iso‐butene/iso‐butylene 24isobutylene 24, 144, 296, 303, 304,

311isolongifolanone 300isomeric butanes 19isomeric butenes 23–24isomeric 6‐dodecenes 24isomerism 20, 33isopentenyl pyrophosphate 270, 272iso‐propyl,‐CH(CH3)2 22isopropyl myristate (IPM) 78isotopes 8

kKaranal 159Karl Fischer method 113Kelvin scale 135ketals 50–52, 61, 62, 158–159, 178ketones 46–47, 54, 112, 128, 142, 159,

169, 177, 178, 180, 183, 199–201, 203, 208, 233, 310, 368

kitchen malodours 279, 280

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Index 389

llactone 49, 50, 177, 279, 314, 318laevorotatory (l‐) 34latent heat of fusion 73latent heat of vaporisation 73, 91laundry powders 133, 152, 154, 158,

170, 179, 192, 202, 211, 212, 352Laureth‐2 77lavandulyl acetate 103l‐carvone 274LD50 231, 232lecithins 79, 83, 224Lewis acids 147–149, 167, 300Lewis base 148Ligustral 45, 55, 144, 159, 305limonene 34

enantiomers of 35linalool 103, 131, 132, 144, 231, 273, 285,

291, 292, 294, 296, 297, 333, 340linear alkyl‐benzene sulfonates

(LAS) 77lipases 199, 213lipids 75

fatty acids 223in living organisms 224phospholipids 224, 225sphingolipids 224, 225triglycerides 224

lipocalins 226, 230, 246lipophilic (oil‐loving) 75liquid bleach 109, 201, 213liquid splitter 89lithium 4, 10, 11lithium fluoride (LiF) 11lithium oxide (Li2O) 11l‐limonene 34l‐menthol 274, 319

BASF route 349from Mentha arvensis 346structure 346sustainability 345Symrise route 347Takasago route 347–348

l‐menthyl benzoate 94log P 15, 16, 75, 191, 211, 233, 239,

246, 324lutensols 78

mmachine dishwashing powders and

gels 213macrocyclic musks 28, 288, 317–319,

343, 345magnesium cation 13magnetic nuclei 120malodour management 353, 354malodours 39, 59, 171, 173, 174, 202,

264, 279–281, 322mammalian cell wall 79, 83, 84, 226mass spectrometry (MS) 102, 107,

114, 124–125, 127basic elements 125ethanol 126fragmentation 126ions fragment 125

matter 1–16, 67–84, 134medium rings 28Mefrosol 191, 308, 309melting point 108Mentha arvensis 346menthol 35

sustainabilityenergy 350–351environmental implications 350feedstocks 349–350

meso‐isomer 36metallurgy 1methane 14–15, 18methanesulfonic acid 60methane thiol 58methanol 40, 41, 69, 216, 217, 263,

295, 315(Z)‐3‐methoxy‐4‐methylhept‐3‐ene 25methyl anthranilate 39, 54, 55, 114,

160, 161, 266, 351, 352methyl carbanion 141methyl dihydrojasmonate 194, 314methyl ethyl 2‐hydroxyethyl salts 952‐methyl‐2‐(1´ethylprop‐1‐yl)

propan‐1,3‐diol 159methylheptenone 166, 293–2953‐methyl‐2‐hexenoic acid 280methyl iso‐amyl ketone 47methyl jasmonate 49, 264, 324, 327methyl ketones 47, 178, 179, 201, 283

bindex.indd 389 2/26/2019 3:26:02 PM

Index390

4(R)‐(+)‐1‐methyl‐4‐(1´‐methylethenyl)cyclohex‐1‐ene 24

2‐methylpropane 20methyl radical 22, 25, 40, 126, 131,

141methyl vinyl ketone 233meting or fusion 73mevalonic acid 261, 270micelles 81, 212Michael acceptors 233, 235Michael reaction 164–165, 233, 314molecular orbital 14, 114, 117molecular recognition

chirality 217defined 215electrostatic attraction 215hydrogen bonding 216–217hydrophobic bonding 217–218van der Waals attraction 215

monosaccharides 219–221monoterpenoid acetate 103monoterpenoid alcohol 103monoterpenoids 103, 268–270,

272–276muguet aldehydes 306–307musk ingredients 297, 343musk ketone 57, 58, 343mutagenic materials 234myrcene 103, 298, 347

nn‐alkanes, boiling points 22naphthalene 309–310

numbering systems 33naphthofuran 278, 301, 302natural chemicals, classes of 218natural fragrance ingredients 340

estraction 95naturally sourced ingredients 337Nazarov reaction 318n‐butane 20neural pathways, in olfactory

perception 255neutralisation of sulfuric acid

(H2SO4) 136neutral surfacants 78Newman projection 18

nicotinamide adenine dinucleotide phosphate (NADP) 229, 258, 260

Nirvanolide 343nitriles 156, 157, 161–162 see also

cyanidenitrobenzene 57, 58nitro compounds 57nitrogen detection 104nitrogenous molecules 39nitromusks 316, 343n‐Octanol 75non‐soap detergents (NSDs) 76, 211non‐superimposability

of asymmetric carbon atoms 34isomer 33

nootkatone 127, 300, 345normal butane/n‐butane 20nor‐patchoulenol 43novel fragrance ingredient discovery

chemist’s role 322–323copying leads 324high thoroughput screening 323odour character 325performance tests 325random screening 323statistical design 324

n‐pentane 20nuclear magnetic resonance

(NMR) 108, 120–124nucleic acids 218, 221–222nucleophiles 152–154

in consumer goods 200–201reaction, with perfume ingredients 200

nucleosides 221nucleotides 221, 222, 251, 259numerical prefixes 21, 24, 26

oocimene 103octenylsuccinic acid (OSA) 78odorous molecules 17, 39, 221, 245,

246, 257, 336odour binding proteins 226, 245–247,

354odour perception 36, 245, 252–256,

324, 353, 355odour properties 198, 320, 323, 326

bindex.indd 390 2/26/2019 3:26:02 PM

Index 391

OECD test 235olefins 23, 24

acid catalyzed addition to 163–164metathesis 318

olfaction 41, 353combinatorial nature 249–252organs used in 244–246receptor event 247–249role in biology 243transport to receptors 246–247

olfactory epithelium 245, 256, 353, 354olfactory receptor proteins 225, 227,

247–250oligomerisation 302, 303oligosaccharides 219opacifiers 207optical brighteners 207optical rotation 109, 336orbitals

hybridisation of 11–12shape of 9–10

organic compounds 17, 101, 102, 165, 172, 178, 221

organic reactions 140–145organoleptic analysis 198organosulfur compounds, oxidation

of 173organs used, in olfaction 244orsellinic acid 2633‐oxapentane 441,3‐oxathiane 61oxazolidine 62oxidation and reduction (red‐ox)

reactions 171chromium 171–172iron 171–172

oxidative decarbonylation, of aldehyde 183

oximes 54, 55, 112oxirane 61oxygenated organics, oxidation levels

of 177–178oxygen bleaches 177, 179

ppalm kernel oil (PKO) 76palm oil (PO) 76, 224

paper chromatography 96, 98paraffins 18para‐tertiary‐butylcyclohexanol

(PTBCHol) 138para‐tertiary‐butylcyclohexyl acetate

(PTBCHA) 138, 155patents 286, 322, 324, 326, 329, 330,

332pearlisers 207pentane 20, 26peracetic acid 180, 202perception of odour 252–256perfume

aldehydes and muguet notes 190base notes 189–190bloom 193–194detection threshold 192impact 192ingredients 187

dihydroxyacetone reaction with 208

nucleophiles reaction with 200middle/heart notes 189–190molecules 75, 205, 208, 210, 246muguet and sandalwood notes 190notes, chords and discords 187odour families 188persistence and tenacity 191physical and chemical factors 194radiance 193–194recognition threshold 192requirement of 187scent trail 194stability 198, 210top notes 188, 190types of 192

perfumery nitriles 57pericyclic (or electrocyclic)

reactions 144periodic table of elements 4, 5Perkin triangle 87peroxide 52, 59, 111, 176, 182, 233peroxy compounds 52peroxy species, in organic

chemistry 176Persil 202personalised perfumes 354

bindex.indd 391 2/26/2019 3:26:02 PM

Index392

personal wash products 211phase transition 72, 73phenols 44, 112, 310–312

antiseptic 43in essential oils 44

phenylacetaldehyde dimethyl acetal (PADMA) 51, 306

phenylethanol 43, 91, 191, 2662‐phenylethanol 305, 342pheromones 243, 257phosphate esters 49, 221phosphatidylcholine 83, 224phospholipids 224, 225phosphoric acid 49, 224, 258photo‐active agents, in consumer

goods 206photosynthesis 261phototoxic materials 234pinane ring system 29π‐electrons 32

of naphthalene 32system of vanillin 158

π*‐orbitals 117plant derived feedstocks, advantage

of 287platinum metals 5polarising filters 33polar solvents 13, 15polycyclic musks (PCMs) 316, 317,

343polyketide biosynthesis 262–263polymerisation 257, 302, 303, 318polypeptides 225, 227polysaccharides 219, 221pomade 94, 95p‐orbitals 10prenyl pyrophosphate 270primary metabolites

carbohydrates 218–221defined 218lipids 223–225proteins 225–230

principle of chemical equilibrium 137–138

principle of microscopic reversibility 137–138

process patent 330

pro‐drugs 351pro‐fragrance system 351proteases/peptidases 199proteins 226

chemical communication 226globular 228lipocalins 226primary structure 227secondary structure 227tertiary structure 228–229

protium 8protons 7, 8, 10, 12, 13, 128, 129,

141, 163PTBCHA formation and loss 155p‐toluenesulfonic acid 60

qquality control (QC) 107, 131–132quantitative structure‐activity

relationships (QSAR) 324quaternary ammonium salts 53, 78,

79, 258quats 53, 78

rracemate 36, 333, 347racemic mixture 36, 94, 347radiance 193, 194, 320radioactive isotopes/radio‐isotopes 8,

104, 132, 261radio frequencies 107, 120(R)‐and (S)‐nomenclature 36raw materials, for fragrance

ingredients 288reaction profiles 138–140readily biodegradable substance 235receptor event, olfaction 247receptor odorant screening map 251reductants in, consumer goods 202–204reflux 88, 89refractive index 100, 109, 131refractometer 109regular polygons 26, 27Research Institute for Fragrance

Materials (RIFM) 238resinoid 95resolution 36

bindex.indd 392 2/26/2019 3:26:02 PM

Index 393

resonance 32reviews and books 331RIFM Expert Panel (REXPAN) 239rose alcohols 273, 291, 296rule of thumb 138, 197

ssaccharides 218–219, 221sandalwood ingredients 290, 343–344sandalwood oil 276, 340, 344Santalum album 340saponification 75saturated hydrocarbons 177saturated solution 74scented candles 212scent trail 194Schiff ’s bases 54–55, 160–161, 178,

200schizophrenic acid 48, 280SciFinder 332, 333sclareolide 301, 302, 344secondary metabolites 218

biosynthesis of 261–262second law of thermodynamics 134semiochemicals 257sense of smell 2, 131, 215, 243, 244,

250, 254separation and purification

crystallisation 93–94distillation 85–93

azeotropes, formation of 90Dean and Stark apparatus 90fractionating still 89hydrodiffusion 91under reduced pressure 87steam still 91

natural fragrance ingredients estraction 95

sublimation 93sesquiterpenoid hydrocarbons 103,

200sesquiterpenoids 103, 268, 275–276shikimate raw materials, for fragrance

ingredient production 288shikimic acid 261, 265–267σ*‐orbital 117silicones 78, 100

skew conformations 18skin irritation 232, 234, 239skin sensitisation 232–234, 239sodium bisulfite (NaHSO3) 200, 202sodium cation 13, 67sodium chloride 13, 208

crystal 67, 68crystal lattice, fragment 14

sodium cumenesulfonate (SCS) 77sodium hydroxide (NaOH) 75–76, 136sodium hypochlorite 109, 174, 175,

186, 201sodium ion 67, 74sodium lauryl ether sulfate (SLES) 77sodium nonanoyloxybenzenesulfonate/

percarbonate bleach system 202

sodium or potassium 75, 111sodium sulfate (Na2SO4) 136soft electrophiles 153, 233, 234solid shading 14, 34solubility 43, 74–75, 85, 91, 93, 96,

164, 234, 239solute 74solvent 2, 13, 16, 69, 74

extraction 94soot/carbon black 69space‐filling model 15spectrometers 113

basic components 116spectroscopic techniques 114, 115,

127–131spectrum, of red dye 116–117sphingolipids 224, 225sphingomyelin 83, 225sp3 orbitals 11, 12, 14staggered conformation 18, 28standard temperature and pressure

(STP) 21states of matter

bilayers 82–84colloids 84detergency 81–82emulsions 79–81gas 71liquids 71micelles 81

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Index394

states of matter (contd.)simple phase diagram 72solids

crystalline solid 68cubic crystal lattice 67, 68diamond crystal structure 70graphite 70soot/carbon black 69

surfactants, oil/water interface 76stereoisomerism 33–36stereoisomers 34–37, 346, 349steroids 95, 269, 277storage conditions, of perfumes 197structure‐activity relationships

(SAR) 324structure‐odour

relationship 324–325s‐type orbital 9styrene monomer/propylene oxide

(SMPO) process 305sub‐critical water 95sublimation 93sulfate esters 49, 59sulfate turpentine 290, 296, 337, 341,

342sulfonate 59, 77sulfonic acids 59–60, 77, 169, 173sulfonyl chlorides 59, 60sulfoxides 59, 173sulfur 3, 39, 58, 104

divalent sulfur compounds 58hexavalent 60molecule 39oxidation states of 172oxoacids, structure of 175thio‐ether 59thiols or mercaptans 58

sulfuric acid 49, 59, 60, 98, 136, 148, 149, 173, 230, 288, 316

super‐saturated solution 74surface active agents 53, 75, 204surfactants 75

anionic surfacants 77cationic surfacants 79in consumer goods 205DEFI 77LAS 77

neutral surfacants 78sulfonic acids 77two‐phase systems 73

sustainability, in fragrance industrydefinition 335health and wellbeing and perfume/

sense of smell 355–356malodour management 354natural fragrance

ingredients 340–341social and health factors 353–356synthetic ingredients 341–351understanding olfaction 353–354

Symrise route, to l‐menthol production 347

synperonics 77synthetic fragrance ingredients 283

biotechnology 345environmental impact 342–344factors for the use of 283legal labelling requirements 284l‐menthol 345safety 284secure supply using chemical

process 284stability issues 283use of by‐products 341

tTakasago route, to l‐menthol 347–348tartaric acid 36tautomers 54, 155, 156, 160, 208temperature ramping 101tenacity, odour 320terpeneless oil 92terpenoids 95, 267, 290

building blocks 270, 271defined 268isoprene and head‐tail linkage

in 269isoprene units, mechanism of

coupling 270, 271terpineol 103, 297tertiary‐butyl,‐C(CH3)3 22tertiary‐butyl carbocation 143tetraacetylethylenediamine (TAED)

activators 179, 180, 202

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Index 395

1,1,1,2‐tetrafluoroethane 95tetrahedron 12, 14, 17, 53, 59, 331tetrahydrofuran 61, 165tetrahydropyran 61tetrahydrothiophene 61tetramethylsilane (TMS) 121thermodynamics 133–135thiazolidine 62thin layer chromatography (TLC) 96,

98–99thio‐ether 58, 59, 173, 174, 202thioglycolic acid 200–204thiols or mercaptans 58thiomethanol 58thionyl chloride (SOCl2) 50thioterpineol 59thyme 44tincture 94titration 110–113, 198, 221tobacco smoke malodour 280tocopherol 185, 203toxicology 230–231trail 194, 3201,3‐trans 24trans‐2‐butene 23trans‐6‐dodecene 247‐transmembrane G‐protein coupled

receptors 247Traseolide 149trickle down 195triglycerides 224trihydric alcohol glycerol 1592,6,6‐trimethylbicyclo[3.1.1]hept‐2‐

ene 291,3,5‐trioxane 61, 159triphenylmethane dyes 206triple bonds 26, 28, 56triple point 721,2,4‐trisubstituted aromatic ring 128triterpene ambreine 278tritium 8trivial names 24, 32, 45, 46, 48, 57, 68turpentine 28, 31, 86, 187, 238, 274,

288, 290, 291, 296, 300, 302, 326, 337, 341, 342, 350

2s orbital 9, 22

uultimately biodegradable

substance 235Ultravanil 158ultraviolet (UV) 100, 113–120, 206,

352ultraviolet/visible (UV/Vis) 107, 113unit cell, of crystal 67unwanted acetal formation 160unwanted aldol condensations 157

vvalence 4, 9–11, 14, 19, 56, 148, 171,

300, 345Van der Waals interactions 68–69vanillin 158, 210, 288, 311vapor pressure 73vapour phase chromatography

(VPC) 96vapour splitting device 89vegetable oils 15, 75, 199, 288viscosity 109visualisation 97–99vitamin B12 5volatility, perfume ingredients 191

wWagner–Meerwein

rearrangement 273wanted acetal formation 160wanted aldol condensations 157water (H2O) 2, 3, 13, 15, 77, 112–113,

136of cohobation 91

woody odorants 247, 342, 352ω‐oxidation 236

xxylene 32

yylang‐ylang 39, 190Ysamber K 52

zZwitterionic surfactants 79, 80

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