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Muscone

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CAS:541-91-3
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Related articles

Muscone Basic information
Product Name:Muscone
Synonyms:MUSCONE;3-methylcyclopentadecan-1-one;3-methyl-cyclopentadecanon;3-METHYL-1-CYCLOPENTADECANONE;3-METHYL-CYCLOPENTADECANONE;Cyclopentadecanone, 3-methyl-;Cyclopentadecanone,3-methyl-;Methylexaltone
CAS:541-91-3
MF:C16H30O
MW:238.41
EINECS:208-795-8
Product Categories:Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:541-91-3.mol
Muscone Structure
Muscone Chemical Properties
Melting point -15°C(lit.)
Boiling point 95°C/0.1mmHg(lit.)
density 0.9221
vapor pressure 0.041Pa at 25℃
FEMA 3434 | 3-METHYL-1-CYCLOPENTADECANONE
refractive index 1.4770 to 1.4810
RTECS GY0950000
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Methanol (Sparingly)
form Colorless oil.
color Colourless
Odorat 10.00 % in dipropylene glycol. sweet musk animal powdery fatty natural
Odor Typemusk
biological sourcemouse
Water Solubility 430μg/L at 20℃
λmax285nm(EtOH)(lit.)
Merck 14,6313
JECFA Number1402
Major Applicationfood and beverages
Cosmetics Ingredients FunctionsPERFUMING
InChI1S/C16H30O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15H,2-14H2,1H3
InChIKeyALHUZKCOMYUFRB-UHFFFAOYSA-N
SMILESO=C1CC(CCCCCCCCCCCC1)C
LogP6.06 at 25℃
CAS DataBase Reference541-91-3(CAS DataBase Reference)
NIST Chemistry ReferenceCyclopentadecanone, 3-methyl-(541-91-3)
EPA Substance Registry SystemCyclopentadecanone, 3-methyl- (541-91-3)
Safety Information
WGK Germany WGK 3
TSCA TSCA listed
HS Code 2914.29.5000
Storage Class10 - Combustible liquids
Hazardous Substances Data541-91-3(Hazardous Substances Data)
MSDS Information
Muscone Usage And Synthesis
Chemical PropertiesMuscone 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 PropertiesMusk 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 Properties3-Methyl-1-cyclopentadecanone has a soft, sweet, tenacious, musky odor.
Chemical PropertiesColorless oily liquid
OccurrenceReported found in natural musk
UsesMuscone protects PC12 cells against glutamate-induced apoptosis.
PreparationFrom condensation of dodecamethyl-ene-α,ω-dimethylketone hexadecane.
Aroma threshold valuesDetection: 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 ExplosibilityNot classified
Biological Activitymuscone 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 ProfileLow oral and skin contact toxicity. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
SynthesisStarting 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 vitromuscone 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 vivoin 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).
[4] WOLFGANG OPPOLZER   Rumen N R. Synthesis of (R)-(-)-muscone by an asymmetrically catalyzed macrocyclization of an .omega.-alkynal[J]. Journal of the American Chemical Society, 1993, 115 4: 1593-1594. DOI:10.1021/ja00057a064.
Muscone Preparation Products And Raw materials
Raw materials1,3-Butadiene-->Semicarbazide-->Fragrance stabilizer-->Cyclopentadecanone
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