Essential Oils Composition KIMIA MINYAK ATSIRI. ESSENTIAL OIL COMPOSITION Essential Oils are complex...

Essential Oils Composition

KIM

IA M

INYA

K AT

SIRI

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-cis-undecatriene 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 Mulberry, green tea

Freshly cut grass

Cis-2-hexen-1-ol fruits Sweet aroma

1-octen-3-ol Lavender oil Earthy-forest

3-0ctanol mushroom mushroom

Aliphatic Aldehydes / Keton

• Aliphatic Aldehydes are important compounds in perfumery and flavouring, but keton have limited role in odour.

Aliphatic Aldehydes/Ketones origin Odour

n-octanal, n-nonanal, n-decanal, n-undecanal,

Citrus oil

Trans-2-hexenal many Leaf oils Sharp-herbal

3-hydroxy-2-butanon (acetoin) and diacetyl (2,3-butanedione)

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) – monoterpenes15- 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. LIMONENEii. MENTHOLiii. 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

GERANIALCYCLIC TERPENOID (ALCOHOL, KETONE)BASED ON FUNGTIONAL GROUPS:ALCOHOLKETON/ALDEHYDEESTER

B. BENZENE DERIVATIVES (AROMATIC COMPOUNDS)

The Compounds containing benzene ring

E.g. Vanillin OH

OCH3

CHOOH

OCH3

eugenolclove oil

BENZENA DERIVATIVEs

p-cymenemany essential oils

citrus odour

OCOCH3

benzyl acetatejasmine oil

O

O

benzyl benzoatPeru Balsamheavy blossom

O

OH

O

methyl salicylatewintergreen oil

MISCELLANEOUS COMPOUNDS

O

CIS-JASMONE

O

A-VETIVONE

O

ROSE OXIDE

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