5-Cyclohexadecenone

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
Identifiers
CAS Number	37609-25-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3188464;
ChemSpider	26547690;
ECHA InfoCard	100.048.681
EC Number	253-568-9;
PubChem CID	162268;
UNII	1DAH7E9E0D ;
CompTox Dashboard (EPA)	DTXSID8047139 ;
	InChI 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;
	SMILES C1CCCCCC(=O)CCCC=CCCCC1;
Properties
Chemical formula	C16H28O
Molar mass	236.399 g·mol−1
Appearance	Colorless clear liquid
	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

^ a b 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.
^ a b c "Ambretone" (PDF). takasago.com.
^ Alvin S. Williams (1999). "The Synthesis of Macrocyclic Musks". Synthesis. 1999 (10): 1707–1723. doi:10.1055/s-1999-3581. S2CID 196729693.
^ a b "Musk amberol". thegoodscentscompany.com.
^ a b c "5-CYCLOHEXADECEN-1-ONE". chemicalbook.com.
^ 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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[McGinty-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.

[takasago-2] "Ambretone" (PDF). takasago.com.

[Williams-3] Alvin S. Williams (1999). "The Synthesis of Macrocyclic Musks". Synthesis. 1999 (10): 1707–1723. doi:10.1055/s-1999-3581. S2CID 196729693.

[thegoodscentscompany-4] "Musk amberol". thegoodscentscompany.com.

[chemicalbook-5] "5-CYCLOHEXADECEN-1-ONE". chemicalbook.com.

[Watanabe-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.