541-91-3 Usage
Description
Muscone, also known as 3-Methyl-1-cyclopentadecanone, is an odoriferous constituent of natural musk. It is a colorless liquid with a very soft, sweet, musky odor and a perfumery, animal tonality. Due to its excellent stability, it can be used in a wide range of products to give elegant, warm, animal notes. It is important for the reconstitution of natural musk.
Uses
Used in Fragrance Industry:
Muscone is used as a fixative and base note ingredient in the fragrance industry for its excellent stability and ability to provide elegant, warm, animal notes to perfumes and other scented products.
Used in Pharmaceutical Industry:
Muscone is used as a protective agent for PC12 cells against glutamate-induced apoptosis, indicating its potential use in the development of treatments for neurodegenerative diseases.
Used in Musk Reconstitution:
Due to the prohibition of hunting Moschus species and the high price of natural musk, Muscone is used as an important component in the reconstitution of natural musk, providing a more sustainable and cost-effective alternative for the fragrance industry.
Preparation
From condensation of dodecamethyl-ene-α,ω-dimethylketone hexadecane.
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].
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).
Check Digit Verification of cas no
The CAS Registry Mumber 541-91-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 1 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 541-91:
(5*5)+(4*4)+(3*1)+(2*9)+(1*1)=63
63 % 10 = 3
So 541-91-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H30O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15H,2-14H2,1H3