essential oils composition kimia minyak atsiri. essential oil composition essential oils are complex...
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Essential Oils Composition
KIM
IA M
INYA
K AT
SIRI
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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
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Essential Oils Composition
Component of Essential Oils can be classified into 4 major groups :
• ALIPHATIC COMPOUNDS• TERPENE AND TERPENE
DERIVATIVES• BENZENE DERIVATIVES• MISCELLANEOUS
COMPOUNDS
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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
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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
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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
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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
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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.
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CLASSIFICATION OF TERPENES
All terpenes are formed from 5-C elements
Isoprene is the basic structural element.
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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.
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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.
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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
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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
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Bicyclic Monoterpene
• There are 5 bicyclic monoterpenes : thuyene, carene, pinene, camphene, and fenchene.
a-thuyene a-pinene b-pinene camphene
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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
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terpenoid
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EXAMPLES OF TERPENES
i. LIMONENEii. MENTHOLiii. SESQUITERPENES
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i. LIMONENE
Structural classification: Monocyclic terpene
Functional Classification: Unsaturated HC
Occurrence: Citrus fruit
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ii. MENTHOL
Structural classification:Monocyclic with hydroxyl group
Functional classification: Alcohol
Occurrence: Peppermint
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iv. SESQUITERPENES(Contain 3 isoprene units)
Acyclic – E.g. Farnesol
Monocyclic – E.g. Bisobolol
Bicyclic e.g. Chamezulene (Chamomile)
B-farnesene caryophyllene
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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
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B. BENZENE DERIVATIVES (AROMATIC COMPOUNDS)
The Compounds containing benzene ring
E.g. Vanillin OH
OCH3
CHOOH
OCH3
eugenolclove oil
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BENZENA DERIVATIVEs
p-cymenemany essential oils
citrus odour
OCOCH3
benzyl acetatejasmine oil
O
O
benzyl benzoatPeru Balsamheavy blossom
O
OH
O
methyl salicylatewintergreen oil
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MISCELLANEOUS COMPOUNDS
O
CIS-JASMONE
O
A-VETIVONE
O
ROSE OXIDE
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