myristoleic acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 434947488

| ImageFile=Myristoleic acid.png

| ImageSize=200px

| PIN=(9Z)-Tetradec-9-enoic acid

| OtherNames=9-Tetradecenoic acid
9-cis-Tetradecenoic acid
cis-Δ⁹-Tetradecenoic acid
Myristolenic acid
Oleomyristic acid

|Section1={{Chembox Identifiers

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

| CASNo=544-64-9

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

| UNII = RF23WGD123

| PubChem=5281119

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444564

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 27781

| SMILES = O=C(O)CCCCCCC\C=C/CCCC

| InChI = 1/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

| InChIKey = YWWVWXASSLXJHU-WAYWQWQTBZ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YWWVWXASSLXJHU-WAYWQWQTSA-N

}}

|Section2={{Chembox Properties

| C=14 | H=26 | O=2

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme Stearoyl-CoA desaturase-1, but it is uncommon in nature.[http://www.lipomics.com/fatty_acids/9-tetradecenoic-acid Myristoleic acid] {{Webarchive|url=https://web.archive.org/web/20120317090028/http://www.lipomics.com/fatty_acids/9-tetradecenoic-acid |date=2012-03-17 }} at Lipomics.com One of the major sources of this fatty acid is the seed oil from plants of the family Myristicaceae, comprising up to 30 per cent of the oil in some species.[http://www.cyberlipid.org/fa/acid0002.htm Monoenoic acids] {{Webarchive|url=https://web.archive.org/web/20121023071304/http://www.cyberlipid.org/fa/acid0002.htm |date=2012-10-23 }} at CyberLipid.org It is a constituent of Serenoa or Saw palmetto, and appears to have activity against LNCaP prostate-cancer cells.{{cite journal|last1=Iguchi|first1=K|last2=Okumura|first2=N|last3=Usui|first3=S|last4=Sajiki|first4=H|last5=Hirota|first5=K|last6=Hirano|first6=K|title=Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells.|journal=The Prostate|date=Apr 2001|volume=47|issue=1|pages=59–65|pmid=11304730|doi=10.1002/pros.1047|s2cid=946366}}