FLAVORS AND

FRAGRANCES

Chapter 7

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

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

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

Single Fragrance &

flavor compounds

Some Aliphatic & Aromatic compounds

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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