| Identification | More | [Name]
3-Methylcyclopentadecanone | [CAS]
541-91-3 | [Synonyms]
1-[4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl]ethanone
2',6'-Dimethyl-3',5'-dinitro-4'-tert-butylacetophenone
3-METHYL-1-CYCLOPENTADECANONE
3-METHYL-CYCLOPENTADECANONE
DL-MUSCONE
FEMA 3434
MUSCONE
3-methylcyclopentadecan-1-one
3-methyl-cyclopentadecanon
Cyclopentadecanone, 3-methyl-
Cyclopentadecanone,3-methyl-
Methylexaltone
Moschus ketone
moschusketone
Musk
Muskone
Muskone, methylexaltone
MUSCONE 95%
DL-MUSCONE OR 3-METHYLCYCLOPENTADECANONE
3-Methylcyclopentadecan-1-on | [EINECS(EC#)]
208-795-8 | [Molecular Formula]
C16H30O | [MDL Number]
MFCD00211114 | [Molecular Weight]
238.41 | [MOL File]
541-91-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
-15°C(lit.) | [Boiling point ]
95°C/0.1mmHg(lit.) | [density ]
0.9221 | [vapor pressure ]
0.041Pa at 25℃ | [FEMA ]
3434 | [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 | [Odor]
at 10.00 % in dipropylene glycol. sweet musk animal powdery fatty natural | [biological source]
mouse | [Odor Type]
musk | [Water Solubility ]
430μg/L at 20℃ | [λmax]
285nm(EtOH)(lit.) | [JECFA Number]
1402 | [Merck ]
14,6313 | [Cosmetics Ingredients Functions]
PERFUMING | [LogP]
6.06 at 25℃ | [CAS DataBase Reference]
541-91-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclopentadecanone, 3-methyl-(541-91-3) | [EPA Substance Registry System]
541-91-3(EPA Substance) |
| Hazard Information | Back Directory | [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/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]. | [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]. | [storage]
Store at -20°C | [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). |
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