Transcript 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-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
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
OH
OCH3
E.g. Vanillin
OH
OCH3
eugenol
clove oil
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
O
CIS-JASMONE
A-VETIVONE
ROSE OXIDE
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