Muscone
Page Template:Chembox/styles.css has no content.
Template:Chembox IndexlistTemplate:Chembox CompToxTemplate:Chembox Datapage check| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Lua error in package.lua at line 80: module 'Module:InfoboxImage/data' not found. | |
| Names | |
|---|---|
| Preferred IUPAC name
(3R)-3-Methylcyclopentadecan-1-one | |
| Identifiers | |
| Page Template:Plainlist/styles.css has no content. | |
3D model (JSmol)
|
Page Template:Plainlist/styles.css has no content. |
| ChEMBL | Page Template:Plainlist/styles.css has no content. |
| ChemSpider | Page Template:Plainlist/styles.css has no content. |
| EC Number | Page Template:Plainlist/styles.css has no content. |
PubChem CID
|
Page Template:Plainlist/styles.css has no content. |
| RTECS number | Page Template:Plainlist/styles.css has no content. |
| UNII | Page Template:Plainlist/styles.css has no content. |
| |
| |
| Properties | |
| C16H30O | |
| Molar mass | 238.415 g·mol−1 |
| Density | 0.9221 g/cm3 |
| Melting point | −15 °C (5 °F; 258 K) |
| Boiling point | 328 °C (622 °F; 601 K) |
| Hazards | |
| NFPA 704 (fire diamond) | Page Template:NFPA 704 diamond/styles.css has no content. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Template:Chembox Footer/trackingTemplate:Short description
Muscone is a macrocyclic ketone, an organic compound that is the primary contributor to the odor of deer musk. Natural muscone is obtained from musk, a glandular secretion of the musk deer, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery and for scenting consumer products today is synthetic. It has the characteristic smell of being "musky" (described as "musk, animal, powdery").[1]
Chemical structure and synthesis
The chemical structure of muscone was first elucidated by Leopold Ružička. It is a 15-membered ring ketone with one methyl substituent in the 3-position. It is an oily liquid that is found naturally as the (−)-enantiomer, (R)-3-methylcyclopentadecanone. Muscone has been synthesized as the pure (−)-enantiomer as well as the racemate. It is very slightly soluble in water and miscible with alcohol.
One asymmetric synthesis of (−)-muscone begins with commercially available (+)-citronellal, and forms the 15-membered ring via ring-closing metathesis:[2]
A more recent enantioselective synthesis involves an intramolecular aldol addition/dehydration reaction of a macrocyclic diketone.[3]
Isotopologs
Isotopologs of muscone have been used in a study of the mechanism of olfaction. Global replacement of all hydrogen atoms in muscone was achieved by heating muscone in heavy water (D2O) at 150 °C in the presence of a rhodium on carbon catalyst.[4] It was found that the human musk-recognizing receptor, OR5AN1, identified using a heterologous olfactory receptor expression system and robustly responding to muscone, fails to distinguish between muscone and the so-prepared isotopolog in vitro.[4] OR5AN1 is reported to bind to muscone and related musks such as civetone through hydrogen-bond formation from tyrosine-260 along with hydrophobic interactions with surrounding aromatic residues in the receptor.[5]
References
Page Template:Reflist/styles.css has no content.
- ^ Page Module:Citation/CS1/styles.css has no content."(R)-muscone". Scents and Flavors. Scents and Flavors. Retrieved 29 March 2026.
- ^ Page Module:Citation/CS1/styles.css has no content.Kamat, V. P.; Hagiwara, H.; Katsumi, T.; Hoshi, T.; Suzuki, T.; Ando, M. (2000). "Ring Closing Metathesis Directed Synthesis of (R)-(−)-Muscone from (+)-Citronellal". Tetrahedron. 56 (26): 4397–4403. doi:10.1016/S0040-4020(00)00333-1.
- ^ Page Module:Citation/CS1/styles.css has no content.Knopff, O.; Kuhne, J.; Fehr, S. (2007). "Enantioselective Intramolecular Aldol Addition/Dehydration Reaction of a Macrocyclic Diketone: Synthesis of the Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone". Angew. Chem. Int. Ed. 46 (8): 1307–1310. doi:10.1002/anie.200604518. PMID 17211908.
- ^ a b Page Module:Citation/CS1/styles.css has no content.Block, E.; et al. (2015). "Implausibility of the Vibrational Theory of Olfaction". Proc. Natl. Acad. Sci. USA. 112 (21): E2766–E2774. Bibcode:2015PNAS..112E2766B. doi:10.1073/pnas.1503054112. PMC 4450420. PMID 25901328.
- ^ Page Module:Citation/CS1/styles.css has no content.Ahmed, L.; et al. (2018). "Molecular Mechanism of Activation of Human Musk Receptors OR5AN1 and OR1A1 by (R)-Muscone and Diverse Other Musk-smelling Compounds". Proc. Natl. Acad. Sci. USA. 115 (17): E3950–E3958. Bibcode:2018PNAS..115E3950A. doi:10.1073/pnas.1713026115. PMC 5924878. PMID 29632183.
