Terpenes - ids

advertisement
Madcasim, Nasser Jr. M.
Galan, Pitt Shaughn Mikho

Terpenes are a large and varied class of
hydrocarbons that typically contain either
ten or fifteen carbon atoms built from a
five-carbon building block called isoprene .
isoprene

Naturally occuring hydrocarbons
plants, insects , and animals.
produced by

These molecules are volatile —they tend to
evaporate relatively easily—which allows them to
reach one's nose and trigger the olfactory senses.

They are the major components of resin, and
of turpentine produced from resin. The name
"terpene" is derived from the word "turpentine”.

Terpenes commonly occur in the oils that give
plants their fragrance (essential oils).

Originally the term terpene was resricted to
hydrocarbons, it is now used to include substituted
derivatives too.
Fragrances and perfumes
 Food Additives
 Insecticides
 Aroma Therapy
 Medicines
 Cleaning Products

 Terpenes
are derived biosynthetically
from units of isoprene, which has the
molecular formula C5H8. The isoprene
is the fundamental building block of
terpenes
isoprene
In their structures, isoprene units are joined
together head-to-tail. That is, C1 of the four-carbon
chain of one isoprene unit is joined to C4 of
another. See, for example, the structure of βselenine, below, which is made up of 3 isoprene
units.
Isoprene Rule (C5 Rule)
The basic molecular formula of
terpenes
are
multiples
of
that,
(C5H8)n where n is the number of linked
isoprene units.

Can be linked head to tail in linear
chains or rings.
- consist of a single isoprene unit.

Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one
of the most simple terpenes. It is a clear colorless oil that is
reasonably soluble in water and miscible with most common
organic solvents. It has a fruity odor and is used occasionally
in perfumery.

Geraniol is a monoterpenoid and an alcohol. It is the primary
part of rose oil, palmarosa oil, and citronella oil Java type.

Limonene is a colourless liquid hydrocarbon classified as a
cyclicterpene possessing a strong smell of oranges. It is used
in chemical synthesis as a precursor to carvone and as a
renewably-based solvent in cleaning products.
- -consist of three soprene units and have the molecular formula C15H24.
- The sesqui- prefix means one and a half.

It is the building block of most, and possibly all, acyclic
sesquiterpenoids and is an important starting compound for
organic synthesis.
- are composed for four isoprene units and have the molecular formula C20H32.
- They are derived from geranylgeranyl pyrophosphate
- They are known to be antimicrobial and anti-inflammatory.

Cafestol is a diterpene molecule present in coffee.




Cembrene A, or sometimes neocembrene, is a natural
monocyclic diterpene isolated from corals of the genus Nephthea. It is a
colorless oil with a faint wax-like odor.
Cembrene A itself has little importance as chemical entity, being a
trail pheromonefor termites; however, the chemical structure of cembrene
is central to a very wide variety of other natural products found both in
plants and in animals.
Cembrenes are biosynthesized by macrocyclization of geranylgeranyl
pyrophosphate.
-Terpenes having 25 carbons and five isoprene units, are rare relative to
the other sizes.
- The sester- prefix means half to three, i.e. two and a half.
-consist of six isoprene units and have the molecular formula C30H48.

Farnesyl pyrophosphate FPP is an intermediate in the HMG-CoA
reductase pathway used by organisms in the biosynthesis of
terpenes, terpenoids, and sterols.

Lanosterol is a tetracyclic triterpenoid, which is the compound from
which all steroids are derived.
- contain eight isoprene units and have the molecular formula C40H64.

Lycopene is a bright red carotene and carotenoid pigment and
phytochemical found in tomatoes and other red fruits and vegetables, such
as red carrots, watermelons and papayas but not strawberries or cherries.
Although lycopene is chemically a carotene, it has no vitamin A activity.

Carotene is an orange photosynthetic pigmentimportant
for photosynthesis. Carotenes are all coloured to the human eye. They are
responsible for the orange colour of the carrot, for which this class of
chemicals is named, and for the colours of many other fruits and
vegetables for example, sweet potatoes and orange cantaloupe melon.
- 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.

Chemically, gutta-percha is a polyterpene, a polymerof isoprene,
orpolyisoprene, specifically trans-1,4-polyisoprene.
Download