Chemistry:5-Cyclohexadecenone
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| IUPAC name
Cyclohexadec-5-en-1-one
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| Other names
5-Cyclohexadecen-1-one; Velvione; musk amberol; Ambrettone; musk TM-II[1]
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| Properties | |||
| C16H28O | |||
| Molar mass | 236.399 g·mol−1 | ||
| Appearance | Colorless clear liquid[2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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Tracking categories (test):
5-Cyclohexadecenone is a macrocyclic synthetic musk with the chemical formula C16H28O. It is an unsaturated analog of cyclohexadecanone. It is also similar in chemical structure to the natural musk scents civetone and muscone.[3]
5-Cyclohexadecenone has a strong musk scent[4] with floral, amber, and civet tones.[2] It is used as a substitute for natural musk in perfumes, cosmetics, and soaps.[1][5] Trade names include Ambretone,[2] Velvione,[4] and TM-II.[5]
5-Cyclohexadecenone can exist as either of two cis/trans isomers and the commercial product is typically a mixture of the two.[5] It can be synthesized in a four-step sequence from cyclododecanone.[6]
References
- ↑ 1.0 1.1 D. McGinty, C. S. Letizia (2011). "Fragrance material review on 5-cyclohexadecen-1-one". Food and Chemical Toxicology 49 (Supplement 2): S98–S103. doi:10.1016/j.fct.2011.07.033. PMID 21801780.
- ↑ 2.0 2.1 2.2 "Ambretone". https://www.takasago.com/cgi-bin/pdf/ambretone.pdf.
- ↑ Alvin S. Williams (1999). "The Synthesis of Macrocyclic Musks". Synthesis 1999 (10): 1707–1723. doi:10.1055/s-1999-3581.
- ↑ 4.0 4.1 "Musk amberol". http://www.thegoodscentscompany.com/data/rw1016851.html.
- ↑ 5.0 5.1 5.2 "5-CYCLOHEXADECEN-1-ONE". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9175194.htm.
- ↑ Watanabe, Shoji; Suga, Kyoichi; Fujita, Tsutomu; Gomi, Tetsuo (2007-04-25). "Synthesis of 5-cyclohexadecenone from cyclododecanone" (in en). Journal of Applied Chemistry and Biotechnology 23 (7): 501–504. doi:10.1002/jctb.5020230705. https://onlinelibrary.wiley.com/doi/10.1002/jctb.5020230705.
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