Essential Oils Composition - Universitas Pendidikan Indonesia

Essential Oils Composition - Universitas Pendidikan Indonesia

KIMIA MINYAK ATSIRI Essential Oils Composition ESSENTIAL OIL COMPOSITION

Essential Oils are complex mixture of sometimes hundreds of chemicals compounds. EXAMPLE ;

Cananga Odorata (Cananga Oil) : 37 % b-caryophyllene 12.2% farnasene 10.5% a-caryophyllene 7.6% g-cadinene 5.4% benzyl benzoate 1.8% geranyl acetate 1.7% linalool 1.1% (Z.E)-farnesol 1.1% nerolidol 0.6% geraniol 0.1% benzyl salicylate

Essential Oils Composition Component of Essential Oils can be classified into 4 major groups : ALIPHATIC COMPOUNDS TERPENE AND TERPENE DERIVATIVES BENZENE DERIVATIVES MISCELLANEOUS COMPOUNDS

ALIPHATIC COMPOUNDS Aliphatic Compounds are non-aromatic organic compounds. The chain of C-atoms may be straight, branched, saturated, or unsaturated. Aliphatic Compounds : Aliphatic of Hidrocarbon, alcohol, aldehydes, ketones, or ester Hidrocarbon compounds occur abundantly in foodstuffs such as fruit, but contribute to their odour to a limited extent only. The highly unsaturated hydrocarbons contribute significantly to the odour of essential oils, example: 1,3-trans-5-cisundecatriene and 1,3-trans-5-trans undecatriene in galbanum oil

Aliphatic Alcohol The odour of most aliphatic alcohols is weak and their role as components in fragrance compositions is limited Aliphatic Alcohol Origin Aroma Cis-3-hexen-1-ol

Freshly cut grass Cis-2-hexen-1-ol Mulberry, green tea fruits 1-octen-3-ol Lavender oil

Earthy-forest 3-0ctanol mushroom mushroom Sweet aroma Aliphatic Aldehydes / Keton

Aliphatic Aldehydes are important compounds in perfumery and flavouring, but keton have limited role in odour. Aliphatic Aldehydes/Ketones origin n-octanal, n-nonanal, n-decanal, nundecanal, Citrus oil Trans-2-hexenal

many Leaf oils 3-hydroxy-2-butanon (acetoin) and diacetyl (2,3-butanedione) Odour Sharp-herbal buttery Aliphatic Esters

Aliphatic Esters are important flavour and fragrance compounds occuring widely in nature. Ester Fragrance Acetate of alcohol up to C6 Fruity C8-C12 Blossom

TERPENES AND ITS DERIVATIVES Terpenes, or terpenoids, are the largest group of secondary products (metabolites). They are all formed from acetyl CoA or glycolytic intermediates.

CLASSIFICATION OF TERPENES All terpenes are formed from 5-C elements Isoprene is the basic structural element. CLASSIFICATION OF TERPENES Terpenes are classified by the number of 5-C atoms they contain 10-Carbon terpenes (contain 2 C-5 units) monoterpenes 15- Carbon terpenes (3 C-5 units) are called sesquiterpenes.

20-carbon terpenes (4 C-5 units) are diterpenes. Larger terpenes (30 Carbons) are called triterpenes (triterpenoids), 40 Carbons called tetraterpenes and polyterpenoids. TERPENOIDS Terpenoids contain only the most volatile terpenes (i.e. molecular weight is not too high) mono and sesquiterpenes May occur as oxygenated derivatives, e.g. alcohols, aldehydes, ketones, phenols, oxides & esters.

Monoterpene Monoterpene can be acyclic, monocyclic, or bicyclic (sometimes tricyclic). Acyclic monoterpenes unstable, and some have aslightly aggressive odour and taste of essential oils to a limited extent only. Ex: myrcene , ocimene myrcene ocimene

Cyclic Monoterpenes Cyclic Monoterpenes occurs in considerable amount, but generally contribute relatively little in odour and often serve as starting material for the biological and chemical synthesis. A-terpinene, limonene, terpinolene a-terpinene limonena terpinolene

Bicyclic Monoterpene There are 5 bicyclic monoterpenes : thuyene, carene, pinene, camphene, and fenchene. a-thuyene a-pinene b-pinene camphene

sesquiterpenes Sesquiterpenea are compounds generated from 3 isoprene unit and conforming to the formula C15H24. Sesquiterpenen can be a acyclic (ex.farnesene), bicyclic ( two C6-ring or C6 and C5 ring) or monocyclic (ex. Humulene, C11 ring) B-farnesene caryophyllene

terpenoid EXAMPLES OF TERPENES i. LIMONENE ii. MENTHOL iii. SESQUITERPENES i. LIMONENE Structural classification: Monocyclic terpene Functional Classification: Unsaturated HC Occurrence: Citrus fruit

ii. MENTHOL Structural classification: Monocyclic with hydroxyl group Functional classification: Alcohol Occurrence: Peppermint iv. SESQUITERPENES (Contain 3 isoprene units) Acyclic E.g. Farnesol Monocyclic E.g. Bisobolol Bicyclic e.g. Chamezulene

(Chamomile) B-farnesene caryophyllene TERPENOID BASED ON SKELETON OF C CHAIN: ACYCLIC TERPENOID TERPRENE ALCOHOL, EX GERANIOL ACYCLIC TERPENE ALDEHYDES/KETONE, EX GERANIAL CYCLIC TERPENOID (ALCOHOL, KETONE)

BASED ON FUNGTIONAL GROUPS: ALCOHOL KETON/ALDEHYDE ESTER B. BENZENE DERIVATIVES (AROMATIC COMPOUNDS) The Compounds containing benzene ring E.g. Vanillin OH OCH3

eugenol clove oil OH OCH3 CHO BENZENA DERIVATIVEs O O

O O p-cymene many essential oils citrus odour OCOCH3 benzyl acetate jasmine oil

benzyl benzoat Peru Balsam heavy blossom OH methyl salicylate wintergreen oil MISCELLANEOUS COMPOUNDS O O

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