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CH
CH2
or
Isoprene
(2-methyl-1,3-butadiene)
CH2
CHCH2CH2CCH
or
CH2
tail
tail head
Classification of Terpenes
Class
Number of carbon atoms
Monoterpene
10
Sesquiterpene
15
Diterpene
20
Sesterpene
25
Triterpene
30
Tetraterpene
40
Representative Monoterpenes
-Phellandrene Menthol
(eucalyptus) (peppermint)
Citral
(lemon grass)
Representative
Sesquiterpenes
a-Selinene (celery)
Representative Diterpenes
Vitamin A
Representative Triterpene
Squalene
(shark liver oil)
OPP
3 CH3COH
CH3
HOCCH2CCH2CH2OH
OH
CH3
H2C
Mevalonic acid
O O
CCH2CH2OPOPOH
Isopentenyl pyrophosphate
Isopentenyl pyrophosphate
Dimethylallyl pyrophosphate
OPP +
The carbocation
can lose a
proton to give a
double bond.
The carbocation
can lose a
proton to give a
double bond.
H2O
Geraniol
E double
bond
Z double
bond
Limonene
H
H2O
-Terpineol
-Pinene
-Pinene
3 CH3COH
CH3
HOCCH2CCH2CH2OH
OH
CH3
H2C
Mevalonic acid
O O
CCH2CH2OPOPOH
Isopentenyl pyrophosphate
CH3CCH2CSCoA
S-Acetoacetyl
coenzyme A
CH3CCH2CSCoA + CH3CSCoA
CH3CCH2CSCoA + CH3CSCoA
HO
CH3CCH2CSCoA
CH2COH
O
CH3CCH2CSCoA
CH2COH
O
HO
CH3CCH2CH2OH
CH2COH
O
HO
CH3CCH2CSCoA
CH2COH
O
Mevalonic
acid
HO
OPO3
CH3CCH2CH2OH
CH3CCH2CH2OPP
CH2COH
CH2COH
OPO3
CH3CCH2CH2OPP
OPO3
CH3CCH2CH2OPP
O
CH2
CH2 C
Isopentenyl
O
Pyrophosphate
Phosphorylation is followed by a novel
elimination involving loss of CO 2 and PO43.