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
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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
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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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