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| | Muscone Basic information |
| | Muscone Chemical Properties |
| | Muscone Usage And Synthesis |
| 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. | | Chemical Properties | Colorless oily liquid | | Occurrence | Reported found in natural musk | | Uses | Muscone protects PC12 cells against glutamate-induced apoptosis. | | 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 | Notclassified | | 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). |
| | Muscone Preparation Products And Raw materials |
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