Muscone

Chemical properties

Colorless oily liquid

Chemical properties

Muscone is an odoriferous constituent of natural musk. It is a colorless liquid with very soft, sweet, musky odor and a perfumery, animal tonality.Numerous syntheses have been developed for its preparation including enantioselective methods to obtain the naturally occurring (3R)-enantiomer (l-muscone,. Because of its excellent stability, it can be used in awide range of products to give elegant,warm, animal notes. It is important for the reconstitution of naturalmusk.

Chemical properties

Musk is secreted exclusively by the male animals of Moschus moschiferus, a wild deer living in themountains of Nepal,Tibet, and Mongolia.Thelight yellow secretion with a salve consistency accumulates in the abdominal pouch and probably serves to attract the females. When the pouch is dried, the secretion solidifies to form a brittle, brown mass with a characteristic odor. Since several Moschus species occur, large variations exist in the quality and specifications of musk. Hunting of the animals has been prohibited; therefore, only small quantities ofmusk are occasionally offered at extremely high prices. In the United States and Europe, naturalmusk is no longer used as a fragrance ingredient.

Chemical properties

3-Methyl-1-cyclopentadecanone has a soft, sweet, tenacious, musky odor.

Occurrence

Reported found in natural musk

The Uses of Muscone

Muscone protects PC12 cells against glutamate-induced apoptosis.

What are the applications of Application

Muscone is a potent antiinflammatory agent, cytrochrome P-450 inducer, and apoptosis inhibitor

Preparation

From condensation of dodecamethyl-ene-α,ω-dimethylketone hexadecane.

Aroma threshold values

Detection: 9.8 ppb

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1906, 1980 DOI: 10.1021/jo01298a029
Tetrahedron Letters, 17, p. 2617, 1976

Flammability and Explosibility

Not classified

Biological Activity

muscone is a potent anti-inflammatory agent, which has been implicated in reducing proinflammatory cytokines and end-plate degeneration [1]. muscone is a territorial releaser pheromone in moschus moschiferus. muscone is not produced by humans. muscone is animal pheromone with no effects on humans comparable to those of androstadienone [2]. (±)-muscone is an odoriferous constituent of musk, a glandular secretion originally collected from the male musk deer [3].

Safety Profile

Low oral and skin contact toxicity. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

in vitro

muscone reversed il-1β-induced upregulation of il-1β, tumor necrosis factor α, cyclooxygenase 2, inducible nitric oxide synthase, matrix metalloproteinase 13, aggrecanase 2, and nitric oxide and downregulation of col2α1 and aggrecan. in end-plate cartilage cultures, pretreatment with muscone (6.25, 12.5, 25 μmol/l) inhibited the il-1β-induced phosphorylation of extracellular signal-regulated kinases 1/2 and c-jun n-terminal kinase in a dose-dependent manner [1].

in vivo

in a rat model with induced intervertebral disc degeneration, muscone inhibited the expression of prostaglandin e2, 6-keto-prostaglandin f1α, il-1β, and tumor necrosis factor α and recovered the structural distortion of the degenerative disc [1].

References

[1] liang q q, zhang m, zhou q, et al. muscone protects vertebral end-plate degeneration by antiinflammatory property[j]. clinical orthopaedics and related research, 2010, 468(6): 1600-1610.
[2] jacob s, garcia s, hayreh d, et al. psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone[j]. hormones and behavior, 2002, 42(3): 274-283.
[3] fujimoto, s. ,yoshikawa, k.,itoh, m., et al. synthesis of (r)- and (s)- muscone. bioscience, biotechnology, and biochemistry 66(6), 1389-1392 (2002).