VII Contents Introduction Individual Fragrance and Flavor Materials

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1 VII Contents 1 Introduction History Definition Physiological Importance Natural, Nature-Identical, and Artificial Products Sensory Properties and Chemical Structure Volatility Threshold Concentration Sensory Properties Fragrance Ingredients Flavoring Substances 6 2 Individual Fragrance and Flavor Materials Aliphatic Compounds Hydrocarbons (E,Z)-1,3,5-Undecatriene [ ] ,3-Undecadien-5-yne [ ] Alcohols Octanol [ ] ,6-Dimethyl-2-heptanol [ ] (E)-2-Hexen-1-ol [ ] (Z)-3-Hexen-1-ol [ ], Leaf Alcohol Octen-3-ol [ ] Decen-1 (cipher)-ol [ ] Undecen-1-ol [ ] ,4,5,6,6-Pentamethylheptan-2-ol [ ] (2E,6Z)-2,6-Nonadien-1-ol [ ], Violet Leaf Alcohol Methyl-3-decen-5-ol [ ] Aldehydes and Acetals Hexanal [ ], Caproaldehyde, Aldehyde C Octanal [ ], Caprylaldehyde, Aldehyde C Nonanal [ ], Pelargonaldehyde, Aldehyde C 9 13

2 VIII Contents Decanal [ ], Caprinaldehyde, Aldehyde C Undecanal [ ], Aldehyde C Dodecanal [ ], Lauraldehyde, Lauric Aldehyde, Aldehyde C Tridecanal [ ] Methyldecanal [ ], Methyloctylacetaldehyde, Aldehyde MOA Methylundecanal [ ], Methylnonylacetaldehyde, Aldehyde MNA (E)-2-Hexenal [ ], Leaf Aldehyde (Z)-4-Heptenal [ ] ,6-Dimethyl-5-hepten-1-al [ ] (E)-4-Decenal [ ] Undecenal [ ] Dodecenal [ ] ,6,10-Trimethyl-5,9-undecadienal [ ]and [ ] ,1-Dimethoxy-2,2,5-trimethyl-4-hexene [ ] Ketones Hydroxy-2-butanone [ ], Acetoin ,3-Butanedione [ ], Diacetyl (2E)-5-Methyl-2-hepten-4-one [ ] ,4,5,6,6-Pentamethyl-3-hepten-2-one [ ] ,4,4,7-Tetramethyl-6-octen-3-one [ ] Acids and Esters Methyl-2-pentenoic Acid [ ] Ethyl Formate [ ] (Z)-3-Hexenyl Formate [ ] Ethyl Acetate [ ] Butyl Acetate [ ] Isoamyl Acetate [ ] Hexyl Acetate [ ] ,5,5-Trimethylhexyl Acetate [ ], Isononyl Acetate (E)-2-Hexenyl Acetate [ ] (Z)-3-Hexenyl Acetate [ ] Ethyl Propionate [ ] Ethyl Butyrate [ ] Butyl Butyrate [ ] Isoamyl Butyrate [ ] Hexyl Butyrate [ ] (Z)-3-Hexenyl Isobutyrate [ ] Ethyl Isovalerate [ ] Ethyl 2-Methylbutyrate [ ] Ethyl Hexanoate [ ], Ethyl Caproate Ethyl 2-Methylpentanoate [ ] 24

3 Contents IX Propenyl Hexanoate [ ], Allyl Caproate Ethyl Heptanoate [ ], Ethyl Enanthate Propenyl Heptanoate [ ], Allyl Heptanoate, Allyl Enanthate Ethyl Octanoate [ ], Ethyl Caprylate Methyl 2-Nonenoate [ ] Ethyl (2E,4Z)-2,4-Decadienoate [ ], Pear Ester Methyl 2-Octynoate [ ], Methyl Heptin Carbonate Methyl 2-Nonynoate [ ], Methyl Octin Carbonate Propyl (2S)-2-(1,1-Dimethylpropoxy)propanoate [ ] Ethyl 3-Oxobutanoate, Ethyl Acetoacetate [ ] (Z)-3-Hexenyl Methyl Carbonate [ ] Allyl (3-Methylbutoxy)acetate, Isopentyloxyacetic Acid Allyl Ester [ ], [ ] Allyl Amylglycolate Miscellaneous Compounds Allyl Isothiocyanate [ ], Allyl Mustard Oil Methyl-3-heptanone oxime, N-Hydroxy-5-methyl-3-heptanimine [ ] [(Z)-3-Hexenyloxy]-propanenitrile [ ] N,2,3-Trimethyl-2-isopropylbutanamide [ ] "WS 23" Tridecenenitrile [ ] Acyclic Terpenes Hydrocarbons Alcohols Geraniol [ ], (2E)-3,7-Dimethyl-2,6-octadien-1-ol Nerol [ ], (2Z)-3,7-Dimethyl-2,6-octadien-1-ol Linalool [ ], 3,7-Dimethyl-1,6-octadien-3-ol Myrcenol [ ], 2-Methyl-6-methylene-7-octen-2-ol Citronellol [ ], 3,7-Dimethyl-6-octen-1-ol Dihydromyrcenol [ ], 2,6-Dimethyl-7-octen-2-ol Tetrahydrogeraniol [ ], 3,7-Dimethyloctan-1-ol Tetrahydrolinalool [ ], 3,7-Dimethyloctan-3-ol ,6-Dimethyl-2-octanol [ ], Tetrahydromyrcenol Methoxy-3,7-dimethyl-2-octanol [ ] Farnesol [ ], 3,7,11-Trimethyl-2,6,10-dodecatrien-1 (cipher)-ol Nerolidol [ ], 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol Aldehydes and Acetals Citral [ ], 3,7-Dimethyl-2,6-octadien-1-al Citral Diethyl Acetal [ ], 1,1-Diethoxy-3,7-dimethyl-2,6-octadiene Citronellal [ ], 3,7-Dimethyl-6-octen-1-al Hydroxydihydrocitronellal [ ], "Hydroxycitronellal," 3,7-Dimethyl-7-hydroxyoctan-1-al 44

4 X Contents Methoxydihydrocitronellal [ ], 3,7-Dimethyl-7-methoxyoctan-1-al Hydroxydihydrocitronellal Dimethyl Acetal [ ], 8,8-Dimethoxy-2,6-dimethyloctan-2-ol ,6,10-Trimethyl-9-undecenal [ ] Ketones Geranylacetone [ ], 6,10-Dimethyl-5,9-undecadien-2-one Acids and Esters Geranyl and Neryl Esters Linalyl Esters Citronellyl and Dihydromyrcenyl Esters Miscellaneous Compounds ,7-Dimethyloctanenitrile [ ] Citronellic Acid Nitrile [ ], Citronellyl Nitrile Cyclic Terpenes Hydrocarbons Limonene [ ], 1,8-p-Menthadiene γ-terpinene [ ], 1,4-p-Menthadiene ( )-α-phellandrene [ ], 1,5-p-Menthadiene α-pinene [ ], 2-Pinene, 2,6,6-Trimethylbicyclo[3.3.1]hept-2-ene β-pinene [ ], 2(10)-Pinene Alcohols and Ethers Menthol, p-menthan-3-ol Isopulegol, 8-p-Menthen-3-ol, 5-Methyl-2-(1-methylethenyl)-cyclohexanol [ ], [ ] α-terpineol [ ], 1-p-Menthen-8-ol Terpinen-4-ol [ ], 1-p-Menthen-4-ol cis-4-(isopropyl)cyclohexanemethanol, cis-hexahydrocuminyl Alcohol [ ], cis-p-menthan-7-ol Borneol, endo-2-bornanol [ ] [(l)-Menthoxy]propane-1,2-diol [ ], (l)-menthyl Glyceryl Ether Cedryl Methyl Ether [ ]and[ ] Aldehydes and Ketones Menthone, p-menthan-3-one [ ] Carvone, 1,8-p-Menthadien-6-one Camphor, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one [ ] Fenchone, 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one [ ] Ionones and Homologous Compounds Damascones, 1-(2,6,6-Trimethylcyclohexenyl)-2-buten-1-ones 74

5 Contents XI α-damascone, 1-(2,6,6-Trimethyl-2-cyclohexenyl)-2-buten-1-one [ ]; (Z)-: [ ]; (E)-: [ ] β-damascone, 1-(2,6,6-Trimethyl-1-cyclohexenyl)-2-buten-1-one [ ]; (Z)-: [ ]; (E)-: [ ] β-damascenone [ ], 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one δ-damascone, 1-(2,6,6-Trimethyl-3-cyclohexenyl)-2-buten-1-one [ ]; (E)-1α,2β:[ ] (2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one [ ] ,3,4,6,7,8a-Hexahydro-1,1,5,5-tetramethyl-2H-2,4amethanonaphthalen-8(5H)one [ ] Nootkatone, 4,4a-Dimethyl-6-isopropenyl-4,4a,5,6,7,8-hexahydro- 3H-naphthalen-2-one [ ] Methyl Cedryl Ketone, "MCK," Acetyl Cedrene Esters α,3,3-trimethylcyclohexane-1-methanol Formate [ ] ( )-Menthyl Acetate, ( )-p-menthan-3-yl Acetate [ ] rac-menthyl Acetate [ ] Menthanyl Acetate, Dihydroterpinyl Acetate [ ] Methyl-2-(1-methylethyl)cyclohexyl 2-Hydroxy-propanoate [ ], l-menthyl Lactate α-terpinyl Acetate [ ], 1-p-Menthen-8-yl Acetate Nopyl Acetate [ ], ( )-2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)-ethyl Acetate Bornyl acetate, 2-endo-bornanyl Acetate [ ] Isobornyl Acetate [ ], 2-exo-bornanyl Acetate N-substituted p-menthane-3-carboxamides N-ethyl-p-menthane-3-carboxamide [ ], "WS 3" (1) N-(4-Methoxyphenyl)-p-menthane-3-carboxamide [ ] "WS 12" (2) N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine Ethyl Ester [ ]"WS5"(3) Methyl 2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate [ ] Ethyl 2,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxylate [ ] Guaiyl Acetate [ ] Cedryl Acetate [ ] Vetiveryl Acetate [ ] Miscellaneous Compounds Mercapto-p-menthan-3-one [ ] p-Menthene-8-thiol [ ] Other Cycloaliphatic Compounds Alcohols and Ethers 85

6 XII Contents (4-Isopropylcyclohexyl)ethanol [ ] Cyclohexyl-2-methyl-2-butanol [ ] Methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)butanol [ ] Methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol [ ] (2,2,3-Trimethyl-3-cyclopenten-1-yl)-3-methylpentan-2-ol [ ] Ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol [ ] Methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol [ ] Methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-pentenol [ ] ,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol [ ] [1-Methyl-2-(1,2,2-trimethyl[3.1.0]hex-3- ylmethyl)cyclopropyl]methanol [ ] trans-Isocamphylcyclohexanol [ ] (2,2,6-Trimethylcyclohexyl)hexan-3-ol [ ] ,5,5-Trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol [ ], Ambrinol [[2-(1,1-Dimethylethyl)cyclohexyl]oxy]-2-butanol, [ ] (2,2,7,7-Tetramethyltricyclo[ ](1,6)undec-5-en-5-yl)propan- 1-ol, 2-(2,2,7,7-Tetramethyltricyclo[ ](1,6)undec-4-en-5- yl)propan-1-ol, [ ], [ ] Cyclododecyl Methyl Ether [ ], Methoxycyclododecane (Ethoxymethoxy)cyclododecane [ ] Aldehydes ,4-Dimethyl-3-cyclohexene Carboxaldehyde [ ] (4-Methyl-3-penten-1-yl)-3-cyclohexene Carboxaldehyde [ ] Methyl-4-(4-methyl-3-penten-1-yl)-3-cyclohexene Carboxaldehyde [ ] (4-Hydroxy-4-methylpentyl)-3-cyclohexene Carboxaldehyde [ ] Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal [ ] Ketones Pentylcyclopentanone [ ] Heptylcyclopentanone [ ] ,2,5-Trimethyl-5-pentylcyclopentanone [ ] 95

7 Contents XIII Dihydrojasmone[ ], 3-Methyl-2-pentyl-2-cyclopenten-1-one (Z)-Jasmone [ ], 3-Methyl-2-[(2Z)-2-penten-1-yl]-2-cyclopenten-1-one tert-Pentylcyclohexanone [ ] ,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone [ ] Cyclopentadecanone [ ] (E/Z)-3-Methyl-5-cyclotetradecen-1-one [ ] (Z)-4-Cyclopentadecenone [ ] Methylcyclopentadecanone [ ], Muscone Methylcyclopentadecenone [ ] Cyclohexadecanone [ ] Cyclohexadecen-1-one [ ] (E/Z)-7/8-Cyclohexadecenone (Mixture of Isomers) [ ], [ ] (E/Z)-8-Cyclohexadecenone [ ] (Z)-9-Cycloheptadecen-1-one [ ], Civetone (5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-one [ ] Cyclohexyl-1,6-heptadien-3-one [ ] Spiro[4.5]dec-7-en-7-yl-4-penten-1-one, 1-Spiro[4.5]dec-6-en-7-yl-4-penten-1-one [ ] ,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl Methyl Ketone [ ], (1-1,2,3,4,5,6,7,8-Octahydro-2,3,8,8- tetramethyl-2-naphthyl)ethan-1-one [ ], OTNE (2-Butenylidene)-3,5,5-trimethyl-2-cyclohexene-1-one and Isomers [ ] Methyl 2,6,10-Trimethyl-2,5,9-cyclododecatrien-1-yl Ketone [ ] Hydroxy-3-methyl-2-cyclopenten-1-one; 3-Methyl-2-cyclopenten-2-ol-1-one [ ], Cyclotene (1-Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone [ ] Esters tert-Butylcyclohexyl Acetate [ ], OTBCHA tert-Butylcyclohexyl Acetate [ ], PTBCHA (Z)-3-Hexenyl Cyclopropanecarboxylate [ ] ,7-Methano-3a,4,5,6,7,7a-hexahydro-5 (or 6)-Indenyl Acetate [ ] (or [ ]) Allyl 3-Cyclohexylpropionate [ ] Ethyl 2-Ethyl-6,6-dimethyl-2-cyclohexenecarboxylate [ ], and Ethyl 2,3,6,6-Tetramethyl-2-cyclohexenecarboxylate [ ] 108

8 XIV Contents Allyl Cyclohexyloxyacetate [ ], Cyclohexyloxyacetic Acid Allyl Ester [2-[1-(3,3-Dimethylcyclohexyl)ethoxy]-2-methyl-propyl] Propanoate [ ] [2-[1-(3,3-Dimethylcyclohexyl)ethoxy]-2-oxo-ethyl] Propanoate; 2-(1-Oxopropoxy)-acetic Acid 1-(3,3-Dimethylcyclohexyl)ethyl Ester [ ] Methyl Jasmonate [ ], 3-Oxo-2-[(2Z)-2- pentenyl]cyclopentaneacetic Acid Methyl Ester Methyl Dihydrojasmonate [ ], Methyl (3-oxo-2-pentylyclopentyl)acetate Methyl 2-Hexyl-3-oxocyclopentanecarboxylate [ ] Miscellaneous Compounds ,5-Dimethylbicyclo[3.2.1]octan-8-one oxime [ ] Aromatic Compounds Hydrocarbons Alcohols and Ethers Benzyl Alcohol [ ] Phenylethyl Alcohol [ ], 2-Phenylethyl Alcohol Phenylethyl Methyl Ether [ ] Phenylethyl Isoamyl Ether [ ] Acetaldehyde Ethyl Phenylethyl Acetal [ ] Phenylethyl Alcohol [ ], Styrallyl Alcohol Dihydrocinnamic Alcohol [ ], 3-Phenylpropanol ,2-Dimethyl-3-phenyl-1-propanol [ ] ,2-Dimethyl-3-(3-methylphenyl)propanol [ ] α,α-dimethylphenylethyl Alcohol [ ], 2-Methyl-1-phenyl-2-propanol, α,α-dimethyl Benzyl Carbinol Methyl-4-phenyl-2-butanol [ ], α,α-dimethylphenylethyl Carbinol Methyl-5-phenylpentanol [ ] Methyl-5-phenylpentanol [ ] Methyl-1-phenyl-3-pentanol [ ], Phenylethyl Methyl Ethyl Carbinol Cinnamic alcohol [ ], 3-Phenyl-2-propen-1-ol Aldehydes and Acetals Benzaldehyde [ ] Phenylacetaldehyde [ ] Phenylacetaldehyde Dimethyl Acetal [ ] Dihydrocinnamaldehyde [ ], 3-Phenylpropanal Hydratropaldehyde [ ], 2-Phenylpropanal Hydratropaldehyde Dimethyl Acetal [ ] Methylphenylacetaldehyde [ ] Methyl-5-phenylpentanal [ ] (4-Ethylphenyl)-2,2-dimethylpropanal [ ] 123

9 Contents XV [4-(1,1-Dimethylethyl)phenyl]propanal [ ] Cyclamenaldehyde [ ], 2-Methyl-3-(4-isopropylphenyl)propanal (3-Isopropylphenyl)butanal [ ] tert-Butyl-α-methyldihydrocinnamaldehyde [ ], 2-Methyl-3-(4-tert-butyl-phenyl)propanal, BMHCA Methyl-3-[4-(2-methylpropyl)phenyl]propanal [ ] Cinnamaldehyde [ ], 3-Phenyl-2-propenal α-amylcinnamaldehyde [ ], 2-Pentyl-3-phenyl-2-propenal α-hexylcinnamaldehyde [ ], 2-Hexyl-3-phenyl-2-propenal Ketones Acetophenone [ ], Methyl Phenyl Ketone Methylacetophenone [ ], p-tolyl Methyl Ketone Benzylacetone [ ], 4-Phenyl-2-butanone Methyl 2-Naphthyl Ketone, Methyl β-naphthyl Ketone [ ] Benzophenone [ ], DiphenylKetone Acetyl-1,1,2,3,3,6-hexamethylindane [ ] Acetyl-1,1-dimethyl-6-tert-butylindane [ ] Acetyl-1,1,2,6-tetramethyl-3-isopropylindane [ ] (5,6,7,8-Tetrahydro-3,5,5,6,8,8-hexamethyl-2- naphthalenyl)ethanone [ ], [ ], 6-Acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN) Esters of Araliphatic Alcohols and Aliphatic Acids Benzyl Acetate [ ] Benzyl Propionate [ ] Benzyl Isovalerate [ ] Phenylethyl Acetate [ ] Phenylethyl Isobutyrate [ ] Phenylethyl Isovalerate [ ] Phenylethyl Acetate [ ], Styrallyl Acetate α-trichloromethylbenzyl Acetate [ ] α,α-dimethylphenylethyl Acetate [ ] α,α-dimethylphenylethyl Butyrate [ ] Cinnamyl Acetate [ ] Aromatic Acids Phenylacetic Acid [ ] Esters Derived from Aromatic and Araliphatic Acids Benzoates Phenylacetates Cinnamates Miscellaneous Compounds 139

10 XVI Contents Musk ketone [ ], 3,5-Dinitro-2,6-dimethyl-4-tertbutylacetophenone Cinnamonitrile [ ] Methyl-5-phenyl-2-pentenonitrile [ ] Cyclohexylidene-2-phenylacetonitrile [ ] Methyl Anthranilate [ ] Methyl N-Methylanthranilate [ ] Ethyl-N-methyl-N-(3-methylphenyl)butanamide [ ] Phenols and Phenol Derivatives Phenols, Phenyl Esters, and Phenyl Ethers Diphenyl Ether [ ] Phenoxyacetic Acid 2-Propenyl Ester [ ], Phenoxyacetic Acid Allyl Ester Thymol [ ], 2-Isopropyl-5-methylphenol Anethole [ ], 1-Methoxy-4-(1-propenyl)benzene (Cyclopropylmethyl)-4-methoxybenzene [ ] Phenoxyethyl Isobutyrate [ ] Methyl 2-Naphthyl Ether [ ], 2-Methoxynaphthalene, Nerolin Yara-Yara Ethyl 2-Naphthyl Ether [ ], 2-Ethoxynaphthalene, Nerolin Bromelia Isobutyl 2-Naphthyl Ether [ ], 2-(2-Methyl-2- propoxy)naphthalene Hydroquinone Dimethyl Ether [ ], 1,4-Dimethoxybenzene Isoeugenol [ ], 2-Methoxy-4-(1-propenyl)phenol Isoeugenol Methyl Ether [ ], Methyl Isoeugenol Eugenol [ ], 2-Methoxy-4-allylphenol Eugenol Methyl Ether [ ], Methyl Eugenol Eugenol Acetate [ ] Propenylguethol [ ], 2-Ethoxy-5-(1-propenyl)phenol p-cresyl Phenylacetate [ ] Phenol Alcohols and Their Esters AniseAlcohol [ ], 4-Methoxybenzyl Alcohol Anisyl Acetate [ ] Phenol Aldehydes p-anisaldehyde [ ], 4-Methoxybenzaldehyde Methyl-3-(4-methoxyphenyl)propanal [ ] Vanillin [ ], 4-Hydroxy-3-methoxybenzaldehyde Veratraldehyde [ ], 3,4-Dimethoxybenzaldehyde Ethylvanillin [ ], 3-Ethoxy-4-hydroxybenzaldehyde Heliotropin [ ], Piperonal, 3,4-Methylenedioxybenzaldehyde 156

11 Contents XVII Methyl-3-(3,4-methylenedioxyphenyl)propanal [ ] Phenol Ketones Methoxyacetophenone [ ], Acetanisole (4-Hydroxyphenyl)-2-butanone [ ], Raspberry Ketone Phenolcarboxylates Salicylates Resorcylic Acid Esters O-, O,S-andS,S-Heterocycles Cyclic Ethers ,8-Cineole [ ], 1,8-Epoxy-p-menthane, Eucalyptol Rose Oxide [ ], 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran Menthofuran [ ], 3,6-Dimethyl-4,5,6,7-tetrahydrobenzofuran Linalool Oxide, 2-Methyl-2-vinyl-5-(α-hydroxyisopropyl)tetrahydrofuran Butyl-3,6-dihydro-2,4-dimethyl-2H-pyran [ ] ,5,9-Trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene [ ] a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan [ ], [ ], Ambergris Oxide Decahydro-2,6,6,7,8,8-hexamethyl-2H-indeno[4,5-b]furan [ ] Hydroxy-2,5-dimethyl-3(2H)-furanone [ ], Pineapple Ketone Ethyl-4-hydroxy-5-methyl-3(2H)-furanone [ ]and 5-Ethyl-4-hydroxy-2-methyl-3(2H)-furanone [ ], "Homofuraneol" Maltol [ ], 3-Hydroxy-2-methyl-4H-pyran-4-one Ethylmaltol [ ], 2-Ethyl-3-hydroxy-4H-pyran-4-one Isobutyl-4-methyltetrahydro-2H-pyran-4-ol [ ] Pentyltetrahydro-2H-pyran-4-ol Acetate [ ] ,6,6,7,8,8-Hexamethyl-1,3,4,6,7,8- hexahydrocyclopenta[g]benzopyran [ ], "HHCB" Butyl-4,4,6-trimethyl-1,3-dioxane [ ] Isopropyl-9-methyl-1,4-dioxaspiro[4,5]decane-2-methanol [ ], Menthone Glycerine Acetal Hexahydro-1,1,5,5 -tetramethyl-spiro[1,3-dioxolane-2,8 (5 H)- [2H-2,4a]-methanonaphthalene] [ ], [ ] (2,4-Dimethyl-3-cyclohexenyl)-5-methyl-5-(1-methylpropyl)-1,3- dioxane [ ] 173

12 XVIII Contents Dodecahydro-3,8,8,11a-tetramethyl-5H-3,5a-epoxynaphth[2,1- c]oxepin [ ], 8,13;13,20-Diepoxy-15,16-dinor- 8βH-labdane, Ambraketal (4aR,5R,7aS,9R)-Octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9- methanozuleno[5,6-d]-1,3-dioxole [ ] Phenylacetaldehyde glycerine Acetal [ ], 2-Benzyl-1,3-dioxolan-4-methanol ,4,6-Trimethyl-4-phenyl-1,3-dioxane [ ] ,4a,5,9b-Tetrahydroindeno[1,2-d]-m-dioxin [ ] ,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-1,3-dioxin [ ] Methyl-2H-1,5-benzodioxepin-3(4H)-one [ ], Watermelon Ketone Ethyl (2-Methyl-[1,3]dioxolan-2-yl)-acetate [ ], (2-Methyl-[1,3]dioxolan-2-yl)-acetic Acid Ethyl Ester Ethyl (2,4-Dimethyl-[1,3]dioxolan-2-yl)-acetate [ ], (2,4-Dimethyl[1,3]dioxolan-2-yl)-acetic Acid Ethyl Ester (3-Methylbenzofuran-2-yl)-ethanone [ ] cis-2-methyl-4-propyl-1,3-oxathiane [ ] Lactones γ-octalactone [ ](R=n-CH 3 (CH 2 ) 3 ) γ-nonalactone [ ](R=n-CH 3 (CH 2 ) 4 ), the So-Called "Aldehyde C 18 " γ-decalactone [ ](R=n-CH 3 (CH 2 ) 5 ) γ-undecalactone [ ](R=n-CH 3 (CH 2 ) 6 ), the So-Called "Aldehyde C 14 " β-methyl-γ-octalactone [ ], Whiskey Lactone Hydroxy-4,5-dimethyl-2(5H)-furanone [ ], Sotolone Ethyl-3-hydroxy-4-methyl-2(5)-furanone [ ], Abhexone, Maple Furanone δ-decalactone [ ] δ-dodecalactone [ ] Pentadecanolide [ ], 15-HydroxypentadecanoicAcid Lactone Pentadec-11-enolide/15-Pentadec-12-enolide (Mixture of (E)- and (Z)-Isomers) [ ] Hexadecen-16-olide [ ], Oxacycloheptadec-10-en-2-one, Ambrettolide Oxa-16-hexadecanolides ,12-Dodecanedioic Acid Ethylene Ester [ ] ,13-Tridecanedioic Acid Ethylene Ester [ ], Ethylene Brassylate (n = 11) Coumarin [ ], 2H-1-benzopyran-2-one 185

13 Contents XIX Dihydrocoumarin [ ], 3,4-Dihydro-2Hbenzopyran-2-one Glycidates Ethyl 3-Phenylglycidate [ ], the So-Called "Aldehyde C 16 Special" Ethyl 3-Methyl-3-phenylglycidate [ ], the So-Called "Aldehyde C 16," Strawberry Aldehyde Miscellaneous Compounds Furylmethanethiol [ ], Furfuryl Mercaptan N-andN,S-Heterocycles Natural Raw Materials in the Flavor and Fragrance Industry Introduction Isolation of Natural Fragrance and Flavor Concentrates Essential Oils Extracts Survey of Natural Raw Materials Analytical Methods/Quality Control Safety Evaluation and Regulatory Aspects Flavoring Substances Fragrance Ingredients 268 References 271 Formula Index 317 Subject Index 341

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