Essential Oils Composition
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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
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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