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CAS Number 123-35-3
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Linear Formula H2C=CHC(=CH2)CH2CH2CH=C(CH3)2
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Molecular Weight 136.23
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Beilstein Registry
Number 1719990
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EC Number 204-622-5
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MDL number MFCD00008908
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PubChem Substance ID 329759988
Myrcene, or β-myrcene, is an olefinic natural organic hydrocarbon. It is more
precisely classified as a monoterpene. Monoterpenes are dimers of isoprenoid precursors, and myrcene is
one of the most important.
Detailed description
It is a
component of the essential oil of several plants including bay, cannabis, ylang-ylang, wild thyme, parsley,[3] and hops.[4][5] It is produced mainly semi-synthetically from myrcia, from which it gets its name. It is a key
intermediate in the production of several fragrances. α-Myrcene is the name for
the structural isomer 2-methyl-6-methylene-1,7-octadiene, which is not found in
nature and is little used.
Use in fragrance industry
Myrcene is an important intermediate used in the
perfumery industry. It has a pleasant odor, but is rarely used directly. It is
also unstable in air, tending to polymerize. Samples are
stabilized by the addition of alkylphenols or tocopherol. It is thus more highly valued as
an intermediate for the preparation of flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol,
and linalool. Treatment of
myrcene with hydrogen chloride gives geranyl chloride,
neryl chloride, and linalyl chloride. Treatment of these compounds with acetic acid gives geranyl acetate, neryl acetate, and linalyl acetate, respectively. These esters
are then hydrolyzed to the corresponding
alcohols. Myrcene is also converted to myrcenol, another fragrance found in lavender, via uncatalyzed hydroamination of the 1,3-diene followed by
hydrolysis and Pd-catalyzed removal of the amine.
As 1,3-dienes, both myrcene and mycenol undergo Diels-Alder reactions with several dienophiles such
as acrolein to
give cyclohexene derivatives
that are also useful fragrances.
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