THIS IS PART 3 OF THE 4 PARTS OF FLAVOR AND FRAGRANCE INTRODUCTION

1. FLAVORS AND FRAGRANCES
Chapter 7

2. Vanilla extract
Vanilla planifolia
Solvent extraction of the pod
Vanillin, used extensifly in chocolate,ice cream and bake product
Verbena oil
Aloysia triphylla
Steam distillation of leaves
Citral, geraniol & nerol, used in fine fragrances
Vetiver oil
Vetiveria zizanioides
Steam distillation of the root
Sesquiterpene, alpha & beta vetinone & khusimol, vetiverol, used in fine fragrances for long lasting precious wood notes
Violet leaf absolute
Viola odorata
Solvent extraction of the leaves
Violet leaves aldehyde, used in perfumery in very low concentration

3. Essential oil
Plants
Method of prep
Main component
ylang-ylang oils
Cananga odorata
Steam distillation of blossom
Methyl benzoate, linalool, benzyl acetate,geranyl acetate,p-cresol, eugenol & isoeugenol, used in fine fragrances
Cananga oils
Cananga odorata
Steam distillation of the flowers
Same contain as ylang ylang oil plus caryophyllene
Valerian oil
Velerian ofisinalis
Steam distillation of root
Bornyl acetate, terpene & sesquiterpene hydrocarbon & iso valeric acid, used in flavor &fragrance & farmacytical

4. Essential oil
Materials
Method of prepn
Main components
Animal secretions:
bees wax absolute(honey like odor)
Bees wax
Alcohol extraction
Exclusively used in fine fragrances
civet
Civet cat
Fresh secretion is taken from the pouches at intervals
Civet tone and cyclohexadecanone , used in fine fragrances
musk
moschusmoschiferus
The pouches is dried so the secresation solidifies to form a brittle brown, very - very expensive, used in fine fragrances
Muscone and related macrocyclic ketone

5. Single Fragrance & flavor compounds
Some Aliphatic & Aromatic compounds

6. Alcohol
Name of compounds
preparation
properties
3-octanol
By hydrogenation of 3-octanone
Mushroomy-earthtyodorliquid, used in lavender composition
2,6dimethyl-2- heptanol
By reaction of methylmagnesium chloride with 2-methyl2-hepten6-one follow by hydrogenation
Floweryodorliquid used in flowery perfume
Trans-2-hexen-1ol
Fruity greenodorliquid, used in aroma perfumery
Cis 3- hexen-1ol
Reaction of butyne with ethylene oxide followed by hydrogenation by Pd cat
Freshly cut grass odor liquid, used in green top notes in perfume
1-octen-3ol
Reaction of hexanal with vynil magnesium bromide
Mushroomearthy odor liquid, used in mushroom aroma

7. 9-decen-1ol
Dehydration of1,10-decane diol
Rose odor liquid, used as soap perfume
10-undecen-1ol
Synthesize from 10-undesyllenic-acid
Citrus odor liquid, used in flower perfume
Nonaden-1ol
Reaction of Grignard reagent with acrolein
Green violet odor liquid, used in fresh green perfumery

8. Aldehyde & Acetal
Name of compounds
preparation
properties
Hexanal
Fatty aldehydesane generally produced by dehydrogenation of suitable alcohol in the presence of catalyst
Colorless liquid with fatty green odor
Octanal
Colorless liquid with pungent odor which becomes citrus like on dilution
Nonanal
Colorless liquid with fatty rose like odor and is used in floral composition
Decanal
Colorless liquid with strong odor, reminiscent of orange peel but on dilution becomes fresh citrus odor

9. Undecanal
Colorless liquid with a fresh flowerly waxy odor
Dodecanal
Colorless liquid with a fresh flowerly waxy odor but on dilution becomes reminiscent of violets
Tridecanal
Colorless liquid with fatty waxy citrus odor
2-methyldecanal
By product in the manufacture of 2- methylundecanal by hydroformylation of 1-decene
Colorless liquid with citrus peel like waxy green odor
2- methylundecanal
Hydroformylation of 1- decene to give undecanal and 2- methyldecanal.reaction of undecanal with formaldehydegues this product
Colorless liquid with incense and ambergris notes

10. Ketone
Name of compounds
preparation
properties
3-hydroxy-2-butanone
Partial oxidation of 2,3 butandiol
A pleasant buttery odor used for flavoring margarine
2,3-butanedione
Dehydrogenation of 2,3- butandiol with copper chromite as catalyst

11. Acid & Ester
Name of compounds
preparation
properties
Ethyl formate
Esterification of formic and with ethanol
Liquid with a pungent fruity ethered odor
Ethyl Acetate
Esterification of formic acetic acid with ethanol
Liquid has a green fruity odor
Butyl Acetate
Esterification with butanol
Liquid with a strong fruity apple odor
Isoamyl Acetate
Esterification with isoamyl alchohol
Liquid with a strong fruity banana aroma
Hexyl acetate
Esterification with hexanol
Liquid has a sweet fruity pear like odor

12. Isononyl Acetate
From diisobutene by oxosynthesis followed by hydrogenation to alcohol and acetylation
Colorless liquid has a strong woody fruity odor
Trans2-2-hexenyl Acetate
Fresh fruity green smelling liquid
Cis-3-hexenyl Acetate
Found in many fruit aromas
Fruity green smelling liquid
Ethyl propionate
Found in many fruit & alcoholic drinks
Fruity odor reminiscent of rum

13. Acyclic Terpene Hydrocarbon
Name of compounds
preparation
properties
Myrcene
Found in many fruits and essential oils but little use in flavor & fragrances
Acyclic terpene ( C10) and zesquiterpene (C15) hydrocarbons are unstable and have aggressive odor due to their highly unsaturated structure
Ocimene
B-varnesene

14. ACYCLIC TERPENE ALCOHOL
Name of compounds
preparation
properties
Geraniol
Isolation from essential oil of java citronella oil
A colourless liquid with a rose like odor
Nerol
Synthesis from linalool with orthovandatesas catalyst
A colourless liquid with a rose like odor but with a freshly green note
Citronelol
Hydrogenation of citronellal isolated from java citronella oil
A colourless liquid with a sweet rose like odor
Linalool
Isolation from brazillia rosewood oil, shiu oil and corriander oil
A colourless liquid with a flowery fresh odor reminiscent of the lily of the valley

15. Myrcenol
Treating mycene with dialkylamine followed by hydrogenation and deamination
A colourless liquid with a fresh flowery a slight lime like odor
varnesol
Isolation of many blossom essential oils
A colourless liquid with a linden blossom odor which intensily when evaporated

16. Acyclic Terpenes Aldehyde & Acetal
Name of compounds
preparation
properties
Citronelal
Isolation from essential oil, java citronella oil
A colorless liquid with a refreshing odor reminiscent of balm mint
Hydroxycitronelal
Hydration of citronellol followed by dehydrogenation in the presence of Zn –Cu catalyst
Viscous liquid with a flowery odor reminiscent of Linden Blossom and Lily of the valley
2,6,10-trimethyl-9-undcnal
-
Yellowish liquid with intense aldehydewaxy slighthy flowery odor
3,7 dimethyl-7- hydroxyoctan-1-al dimethyl acetal
-
A colorless liquid with warm woody citrus odor
Methoxydihydrocitronelal
-
Liquid with a fresh green blossom odor

17. Acyclic Terpenes Ketones
Name of compounds
preparation
properties
Geranylacetone
-
A colorless liquid with a fresh green rose like odor
Tagetone
-
A major component of tagettes oil

18. Acyclic Terpenes Ester
Name of compounds
preparation
properties
Geranyl formate
Esterification
Liquid with a fresh herbal fruity rose odor
Geranyl Acetate
Same as above
Liquid with a fruity, rose note reminiscent of pear and lavender
Geranyl Propionate
Same
Liquid with a fruity rose odor
Geranyl Isobutyrate
Same
Liquid with a fruity rose odor
Geranyl Isovalerate
Same
Liquid with a strong fruity rose odor
Linalyl, lavandulyl, citronelyl,ester
Same
Liquid with a fresh herbal rose odor

19. Cyclic Terpene Hydrocarbon
Name of compounds
preparation
properties
Limonene
Liquid with lemon odor
Terpinene
Isomerization of limonene
Liquid with a herbaceous citrus odor
d- Pinene
Distillation of turpentine oil
Starting material for synthesis of borned, camphor and terpineol
β- Pinene
Distillation of turpentine oil
Starting material for synthesis of myrcene

20. Cyclic Terpene alcohol
Name of compounds
preparation
properties
Menthol
Isolation from Peppermint oil
Crystal with a peppermint odor with cooling effect
Terpineol
Acid catalyzed hydration of pinenes
Liquid with a strong Lilac odor
Borneol
Isolation from camphor oil, Lavender, rosemary oils
Crystal with camphoraceous odor

21. Cyclic Terpene Aldehyde & ketone
Name of compounds
preparation
properties
Menthone
Distillation of dementholized cornmint oil
Colorless liquid with minty odor
Carvone
Isolation from caraway oil and spearmint oil
Colorless liquid with herbaceous odor reminiscent of caraway and oil seeds
Camphor
Distillation & crystallization of camphor oil
Crystal with cooling effect

22. Aromatic Alcohol & Ethers
Name of compounds
preparation
properties
Benzyl alcohol
Hydrolysis of Benzyl chloride by NaOH /Na 2 CO3
Colorless liquid with weak sweet odor
Phenyl ethyl alcohol
Hydrogenation of styrene Oxide with Raney Ni
Colorless liquid with mildrose odor
Cinnamic alcohol
Reduction of Cinnamaldehyde
Colorless crystalline solid with hyacinth like balsamic odor
Phenylethyl Isoamyl ether
-
Colorless liquid with green sweet flowery odor of chammomile blossom
Phenylmethyl ether
-
Colorless liquid with sharp, rosy green odor

23. Aldehyde
Name of compounds
preparation
properties
Benzaldehyde
Hydrolysis of benzyl chloride
Colorless liquid with a butter almond odor
Phenylacetaldehyde
Isomerization of styrene Oxide
Colorless liquid with sweet green odor reminiscent of hyacinth
Cyclamenaldehyde
Alkaline condensation of deriv. of benzaldehyde with heptanal
Yellow liquid with a intense flowery odor reminiscent of cyclamen
Cinnamaldehyde
Alkaline condensation of benzaldehyde and acetaldehyde
Yellow liquid with spicy odor reminiscent of cinnamon
Amylcinnamaldehyde
From benzaldehyde and heptanal
Yellow liquid with a flowery fatty odor and jasmin when diluted
Hexylcinnamaldehyde
Alkaline condensation of benzaldehyde with octanal
Yellow liquid with a flowery herbal and jasmin odor

24. Ketone
Name of compounds
preparation
properties
Acetophenone
By product in the Hock phenol synthesis
Colorless liquid with a penetrating sweet odor reminiscent of orange blossom
4-Methylacetophenone
From toluene with acetic anhydride
Colorless crystals with a flowery sweet odor
Benzylacetone
Hydrogenation of benzylidene
Sweet flowery smelling liquid
Benzophenone
Friedel crafts reaction of benzene, benzoyl chloride with aluminium chloride
Colorless crystalline solid with a rosy geranium odor

25. Ester
Name of compounds
preparation
properties
Methyl Benzoate
Esterification of benzoic acid with methanol
Colorless liquid with a strong fruity slighty pnemolic odor
Benzyl benzoate
Transesterification of methyl benzoate with benzyl alcohol
Viscous liquid with weak balsamic odor
Methyl Cinnamate
Isolation from Alpinia essential oils
Colorless crystalline solid with a fruity sweet balsamic odor
Benzyl Cinnamate
Found in balsam oils
Sweet balsamic smelling crystals used as fixative

26. Phenol & derivatives
Name of compounds
preparation
properties
Thymol
Reaction of m.cresol with propylene with Al2 O3 cat
Colorless crystals with spicy herbal reminiscent of thyme
Anethole
Isolation from essential oils
Colorless crystals with an anise like odor and sweet taste
Eugenol
Isolation from clove oils
liquid with clove odor
Isoeugenol
Isomerization of eugenol
Viscous liquid with fineclove odor
Eugenol methyl ether
Methylation of eugenol
Colorless liquid with a mild spicy odor
Isoeugenol methyl ether
Isomerization & Methylation of eugenol
Yellow liquid with a sweetmild clove odor, carnation

27. Eugenol acetat
Acetylation of eugenol with acetic anhydride
Yellowish liquid with fruity clove odor
Isosafrole
Alkali catalysed of safrole
Viscous liquid with a sweet anise like odor
P – cresyl phenyl acetate
Esterification of p-cresol with phenylacetic acid
Crystal with a narcisjus odor and honey note
P, openylguethol
Reaction of p-cresol with phenylacetic acid
Crystal with a sweet vanilla odor

28. Phenol Aldehyde
Name of compounds
preparation
properties
Anisaldehyde
Oxidation of p – cresyl methyl ether peroxy sulfates, with Ag+ as catalyst
Yellowish liquid with a sweet, mimosa hawthorn odor
Vanillin
From waste sulfite liquors (previously from Iso eugenol)
Colorless crystalline solid with odor of vanilla
Veratraldehyde
Methylation of vanillin
Crystals with woody vanilla odor
Ethylvanillin
Similar like vanillin but using guethol
Crystall with vanillin odor 3x stronger
Piperonal
Oxidation of Isosafrole
White crystals with a sweet flowery slighty spicy odor

29. Phenol ketone
Name of compounds
preparation
properties
Acetanisole
Acetylation of anisole
White crystals with sweet odor reminiscent of hawthorn
Raspberry ketone
Alkaline condensation of 4- hydroxy benzaldehyde with acetone
Colorless crystals with a sweet fruity odor reminiscent of raspberry

30. Phenol Carboxylates
Name of compounds
preparation
properties
Methyl salicilate
esterification
Main component of wintergreen oil as liquid with a sweet phenolic odor
Iso amyl salicylate
Same
Colorless liquid with a sweet, clover like odor
Phenylethyl salicylate
Same
Crystalline solid with a weak but long lasting babamic, blossom odor, reminiscent of rose & hyacinth

31. Cyclic ether
Name of compounds
preparation
properties
Cineole
Isolation from eucalyptus oil
Colorless liquid reminiscent of camphor
Rose Oxide
From citronellol
Colorless liquid with a strong odor reminscent of geranium oil
Ethyl maltol
Ethylfurfuryl alcohol is reacted with halogen followed by hydrolysis
White crystalls with a very sweet caramel like odor 6x stronger than maltol

32. Lactone
Name of compounds
preparation
properties
ɣ - undecalactone
Intramolecular cyclization of 10-undecalynic acid with H2SO4
Colorless liquid with a peach like odor
δ - decalactone
Peracid oxidation of 2- pentyl cyclopentanone
Colorless,viscous liquid with a creamy coconut peach like odor