5-Cyclohexadecenone

{{Chembox

| ImageFileL1 = Cis-5-cyclohexadecenone.svg

| ImageSizeL1 = 120px

| ImageFileR1 = Trans-5-cyclohexadecenone.svg

| ImageSizeR1 = 150px

| ImageCaptionL1 = cis-5-cyclohexadecenone

| ImageCaptionR1 = trans-5-cyclohexadecenone

| IUPACName = Cyclohexadec-5-en-1-one

| OtherNames = 5-Cyclohexadecen-1-one; Velvione; musk amberol; Ambrettone; musk TM-II{{Cite journal | doi = 10.1016/j.fct.2011.07.033 | journal = Food and Chemical Toxicology | volume = 49 | issue = Supplement 2 | date = 2011 | pages = S98–S103 | title = Fragrance material review on 5-cyclohexadecen-1-one | author = D. McGinty, C. S. Letizia | pmid = 21801780 }}

| Section1 = {{Chembox Identifiers

| CASNo = 37609-25-9

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1DAH7E9E0D

| ChEMBL = 3188464

| ChemSpiderID = 26547690

| PubChem = 162268

| EINECS = 253-568-9

| SMILES = C1CCCCCC(=O)CCCC=CCCCC1

| StdInChI=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

| StdInChIKey = ABRIMXGLNHCLIP-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=16|H=28|O=1

| Appearance = Colorless clear liquid

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{Cite journal | doi = 10.1055/s-1999-3581 | journal = Synthesis | date = 1999 | volume = 1999 | issue = 10 | pages = 1707–1723 | title = The Synthesis of Macrocyclic Musks | author = Alvin S. Williams | s2cid = 196729693 }}

5-Cyclohexadecenone has a strong musk scent{{cite web | url = http://www.thegoodscentscompany.com/data/rw1016851.html | title = Musk amberol | website = thegoodscentscompany.com }} with floral, amber, and civet tones.{{cite web | url = https://www.takasago.com/cgi-bin/pdf/ambretone.pdf | title = Ambretone | website = takasago.com }} It is used as a substitute for natural musk in perfumes, cosmetics, and soaps.{{cite web | url = https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9175194.htm | title = 5-CYCLOHEXADECEN-1-ONE | website = chemicalbook.com }} Trade names include Ambretone, Velvione, and TM-II.

5-Cyclohexadecenone can exist as either of two cis/trans isomers and the commercial product is typically a mixture of the two. It can be synthesized in a four-step sequence from cyclododecanone.{{Cite journal |last=Watanabe |first=Shoji |last2=Suga |first2=Kyoichi |last3=Fujita |first3=Tsutomu |last4=Gomi |first4=Tetsuo |date=2007-04-25 |title=Synthesis of 5-cyclohexadecenone from cyclododecanone |url=https://onlinelibrary.wiley.com/doi/10.1002/jctb.5020230705 |journal=Journal of Applied Chemistry and Biotechnology |language=en |volume=23 |issue=7 |pages=501–504 |doi=10.1002/jctb.5020230705|url-access=subscription }}