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Muscone



Muscone
Chemical name (R)-3-methylcyclopentadecanone
Chemical formula C16H30O
Molecular mass 238.40 g/mol
CAS number [541-91-3]
Density 0.9221 g/cm3
Melting point -15 °C
Boiling point 328 °C
SMILES O=C1C(C)CCCCCCCCCCCC1
Disclaimer and references

Muscone is an organic compound that is the primary contributor to the odor of musk.

Additional recommended knowledge

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 which 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. One asymmetric synthesis of (-)-muscone begins with commercially available (+)-citronellal, and forms the 15-membered ring via ring-closing metathesis:[1]

See also

References

  1. ^ Kamat, V.P.; Hagiwara, H.; Katsumi, T.; Hoshi, T.; Suzuki, T.; Ando, M. (2000). "Ring Closing Metathesis Directed Synthesis of (R)-(-)-Muscone from (+)-Citronellal". Tetrahedron 56 (26): 4397-4403. Retrieved on 2007-12-30.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Muscone". A list of authors is available in Wikipedia.
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