Classification of
Terpenes
Reporter: Rodriguez, Shaira Marie
Properties of Terpenes
Terpenes have desirable properties for use in food, cosmetics, pharmaceutical
and biotechnology industries.
The genomes of 17 plant species contain genes that encode terpenoid synthase
enzymes imparting terpenes with their basic structure, and cythochrome P450s that
modify this basic structure.
Terpenes are useful active ingredients as part of natural agricultural pesticides.
Terpenes are used by termites of the subfamily Nasutitermitinae to ward off
predatory insects, through the use of specialized mechanism called a fontanellar
gun.
Higher amounts of terpenes are released by trees in warmer weather, and may
be a natural form of cloud seeding.
Terpenes are derived biosynthetically from units of isoprene, which has the
molecular formula C5H8. The basic molecular formulae of terpenes are multiples of
that, (C5H8)n, where n is the number of linked isoprene units. This is called the
isoprene rule or the C5 rule. The isoprene units may be linked together "head to tail"
to form linear chains or they may be arranged to form rings. One can consider the
isoprene unit as one of nature's common building blocks.
ISOPRENE
or 2-methyl-1,3-butadiene, is a common organic compound. In its
pure form it is a colorless volatile liquid. Isoprene is produced by
many plants and animals and its polymers are the main
component of natural rubber.
Just like terpenes, the terpenoids can be classified according to the
number of isoprene units used, such as monoterpenoids (two
isoprene units), sesquiterpenoids (three isoprene units),
diterpenoids (four isoprene units), and sesterterpenoids (five
isoprene units). These lipids can be found in all classes of living
things, and are the largest group of natural products.
Classification of Terpenes
(Base on isoprene units)
• Hemiterpenes
• Monoterpenes
• Sesquiterpenes
• Diterpenes
• Sesterterpenes
Classification of Terpenes
Terpenes Isoprene >Number of Example/s
Units C-atoms
Monoterpenes 2 Grenoil, limonene
and terpineol
Sesquiterpenes 3 Farnesol,
humulene,
farnesene
Diterpenes 4 Cafestol, kahweol,
cembrene,
texadiene
Sesterterpenes 5 Geranylfarnesol
Triterpenes 6 Squalene
Tetraterpenes 8 Lycopene, beta-
carotene
Polyterpenes >100 (C5H8)n Rubber-both
natural and
synthetic
Hemiterpenes
Consist of single isoprene unit. Isoprene itself is considered the only
hemiterpene, but oxygen-containing derivatives such as prenol and isovaleric
acid are hemiterpenoids.
Monoterpenes
Consist of two isoprene units and have molecular formula C10H16.
Examples are: Grenoil, limonene and terpineol.
Sesquiterpenes
Consist of three isoprene units and have the molecular formula
Limonen C15H24.
Terpineo Geranoil
e l
Example: Farnesol, humulene, farnesene
Humulen Farnese
e ne
Diterpenes
Composed of four units and have molecular formula of C20H32. Examples:
Cafestol, kahweol, cembrene, texadiene.
Sesterterpenes Cafestol Cembrene Texadiene
Consist of five isoprene units and have 25 carbons, C25H40. They are rare
relative to other sizes.
Example: Geranylfarnesol
Triterpenes Geranylfarnesol
Consist of six isoprene untis and have the molecular formula C30H48. The linear
triterpene squaline, the major constituent of shark liver oil, is derived from the
reductive cupling of two molecules of farnesyl pyrophosphate.
Squalene
Sesquarterpenes
Composed of seven isoprene units and have the molecular formula C35H56. It is
typically microbial in their origin. Examples: Ferrugicadiol,
tetraprenylcurcumene
Polyterpenes
Consist of long chains of many isoprene units. Natural rubber consists of
polyisoprene in which the double bonds are cis. Some plants produce a
polyisoprene with trans double bonds, known as gutta-percha.
Tetraterpenes
Gutta-percha
Consist of eight isoprene units and have the molecular formula C40H64.
Examples: Lycopene, beta-carotene
Lycopene
Beta-carotene
