Muscone
Encyclopedia
Muscone is an organic compound
that is the primary contributor to the odor of musk
.
The chemical structure of muscone was first elucidated by Lavoslav Ružička
. It consists of a 15-membered ring ketone with one methyl substituent in the 3-position. It is an oily liquid that is found naturally as the (−)-enantiomer
, but synthetic material is typically a racemate. It is very slightly soluble in water and miscible with alcohol.
Natural muscone is obtained from musk, a glandular secretion of the musk deer
, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery today is synthetic. It has the characteristic smell of being "Musk
y". One asymmetric synthesis of (−)-muscone begins with commercially available (+)-citronellal
, and forms the 15-membered ring via ring-closing metathesis
:
Muscone is now produced synthetically
for use in perfume
s and for scenting consumer products.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
that is the primary contributor to the odor of musk
Musk
Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. Musk was a name originally given to a substance with a...
.
The chemical structure of muscone was first elucidated by Lavoslav Ružička
Lavoslav Ružicka
Lavoslav Ružička FRS born as Lavoslav Ružička was a Croatian scientist and winner of the 1939 Nobel Prize in Chemistry who worked most of his life in Switzerland...
. It consists of a 15-membered ring ketone with one methyl substituent in the 3-position. It is an oily liquid that is found naturally as the (−)-enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
, but synthetic material is typically a racemate. It is very slightly soluble in water and miscible with alcohol.
Natural muscone is obtained from musk, a glandular secretion of the musk deer
Musk deer
Musk deer are artiodactyls of the genus Moschus, the only genus of family Moschidae. They are more primitive than the cervids, or true deer, in not having antlers or facial glands, in having only a single pair of teats, and in possessing a gall bladder, a caudal gland, a pair of tusk-like teeth...
, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery today is synthetic. It has the characteristic smell of being "Musk
Musk
Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. Musk was a name originally given to a substance with a...
y". One asymmetric synthesis of (−)-muscone begins with commercially available (+)-citronellal
Citronellal
Citronellal or rhodinal or 3,7-dimethyloct-6-en-1-al is a monoterpenoid, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent....
, and forms the 15-membered ring via ring-closing metathesis
Ring-closing metathesis
Ring-closing metathesis or RCM is a variation on olefin metathesis that allows the closing of previously hard to make rings...
:
Muscone is now produced synthetically
Synthetic musk
Synthetic musks, known as white musks in the perfume industry, are a class of synthetic aromachemicals created by chemist and fragrance companies to emulate the scent of deer musk or other natural musk...
for use in perfume
Perfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...
s and for scenting consumer products.