5-Cyclohexadecenone
cis-5-cyclohexadecenone
trans-5-cyclohexadecenone
Names
IUPAC name
Cyclohexadec-5-en-1-one
Other names
5-Cyclohexadecen-1-one; Velvione; musk amberol; Ambrettone; musk TM-II[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.681
EC Number
  • 253-568-9
UNII
  • InChI=1S/C16H28O/c17-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-16/h6,8H,1-5,7,9-15H2
    Key: ABRIMXGLNHCLIP-UHFFFAOYSA-N
  • C1CCCCCC(=O)CCCC=CCCCC1
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).
Infobox references

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. 1 2 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. 1 2 3 "Ambretone" (PDF). takasago.com.
  3. ↑ Alvin S. Williams (1999). "The Synthesis of Macrocyclic Musks". Synthesis. 1999 (10): 1707–1723. doi:10.1055/s-1999-3581. S2CID 196729693.
  4. 1 2 "Musk amberol". thegoodscentscompany.com.
  5. 1 2 3 "5-CYCLOHEXADECEN-1-ONE". chemicalbook.com.
  6. ↑ Watanabe, Shoji; Suga, Kyoichi; Fujita, Tsutomu; Gomi, Tetsuo (2007-04-25). "Synthesis of 5-cyclohexadecenone from cyclododecanone". Journal of Applied Chemistry and Biotechnology. 23 (7): 501–504. doi:10.1002/jctb.5020230705.
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