Chemical Properties
3-Methyl-1-cyclopentadecanone has a soft, sweet, tenacious, musky odor.
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.
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/jo01298a029Tetrahedron 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].
Synthesis
Starting from propargyl alcohol and 1,12-dibromododecane, a long-chain ω-acetaldehyde intermediate was constructed via alkylation. Subsequently, a key asymmetric macrocyclization reaction was carried out using a chiral amino alcohol ligand to close the chain molecule and introduce a chiral center. Finally, Muscone with the native configuration was efficiently synthesized by catalytic hydrogenation reduction of the double bond.
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).
