5-Cyclohexadecenone

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

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
CAS Number	37609-25-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3188464
ChemSpider	26547690
ECHA InfoCard	100.048.681
EC Number	253-568-9
PubChem CID	162268
UNII	1DAH7E9E0D Y
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[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 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]