Fenchol or 1,3,3-trimethyl-2-norbornanol is a
monoterpenoid
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...
and an
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
of
borneol
Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an '' endo'' position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are foun ...
. It is a colorless or white solid. It occurs widely in nature.
The naturally occurring
enantiomere (1''R'')-endo-(+)-fenchol is used extensively in
perfumery
Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...
. Fenchol gives
basil
Basil (, ; ''Ocimum basilicum'' , also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also kno ...
its characteristic scent, and comprises 15.9% of the volatile oils of some species of
''Aster''.
It is
biosynthesized
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...
from
geranyl pyrophosphate
Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products.
Occurrence
GPP is an intermediate in the isoprenoid ...
via isomerization to
linalyl pyrophosphate.
Oxidation of fenchol gives
fenchone
Fenchone is an organic compound classified as a monoterpenoid and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to those of camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fen ...
.
References
{{reflist
External links
3D-image
Secondary alcohols
Monoterpenes