β-fenchyl Alcohol
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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 formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
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 fou ...
. 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 (, ) is a mixture of fragrance, fragrant essential oils or aroma compounds (fragrances), Fixative (perfumery), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agre ...
. Fenchol gives
basil Basil (, ; , ; ''Ocimum basilicum'' (, )), also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a hardiness (plants), tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" r ...
its characteristic scent, and comprises 15.9% of the volatile oils of some species of ''Aster''. It is
biosynthesized Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme- catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthesis) serve ...
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 thousands of natural product, natural products. Occurrence GPP is an int ...
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. Fench ...
.


References

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3D-image
Secondary alcohols Monoterpenes Cyclohexanols