Terpenes
•Terpenes are natural products that are
structurally related to isoprene.
CH3
H 2C C CH CH2 or
Isoprene
(2-methyl-1,3-butadiene)
Terpenes
•Myrcene (isolated from oil of bayberry)
is a typical terpene.
CH3 CH2
CH3C CHCH2CH2CCH CH2
or
The Isoprene Unit
•An isoprene unit is the carbon skeleton of
isoprene (ignoring the double bonds)
Myrcene contains two isoprene units.
The Isoprene Unit
•The isoprene units of myrcene are joined
"head-to-tail."
head tail
tail head
Representative Monoterpenes
OH O
α-Phellandrene Menthol Citral
(eucalyptus) (peppermint) (lemon grass)
Mentha piperita
Pudina
Representative Monoterpenes
OH O
α-Phellandrene Menthol Citral
(eucalyptus) (peppermint) (lemon grass)
Representative Monoterpenes
α-Phellandrene Menthol Citral
(eucalyptus) (peppermint) (lemon grass)
SOME TERPENES (C10)
CH2OH
OH
geraniol menthol
rose and other flowers peppermint
camphor α-pinene
camphor tree turpentine 8
Cinnamomum camphora
Representative Sesquiterpenes
α-Selinene
(celery)
Apium graveolens
Representative Sesquiterpenes
α-Selinene
(celery)
Representative Sesquiterpenes
α-Selinene
(celery)
SESQUITERPENES
CH3
CH3
CH CH3
guaiazulene CH3
geranium oil
Pelargonium graveolens
CH3
CH3 CH3
caryophyllene
oil of cloves
12
Syzygium aromaticum
….. more sesquiterpenes
CH3
CH3
Cedrus CH3 CH3
cedrene
cedar wood oil
CH3
CH3
Pinus
H3C
longifolene
pine species
13
Representative Diterpenes
OH
Vitamin A
Representative Diterpenes
OH
Vitamin A
Representative Diterpenes
Vitamin A
Representative Triterpene
tail-to-tail linkage of isoprene units
Squalene
(shark liver oil)
TRITERPENES
CH3
CH3 OH CH3
CH3
CH3
CH3 CH3
ambrein
ambergis
Sperm whale
18
TETRATERPENE
β-carotene
carrots
head-to-tail tail-to-tail
head-to-tail
19
Non-Isoprenoid
Terpenes
O
Valerane Eremophilone
β-Vetivone
