Myristoleic acid

Myristoleic acid
Names
Preferred IUPAC name
(9Z)-Tetradec-9-enoic acid
Other names
9-Tetradecenoic acid
9-cis-Tetradecenoic acid
cis-Δ9-Tetradecenoic acid
Myristolenic acid
Oleomyristic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.070
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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- ☒N
    Key: YWWVWXASSLXJHU-WAYWQWQTSA-N ☒N
  • 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-
    Key: YWWVWXASSLXJHU-WAYWQWQTBZ
SMILES
  • O=C(O)CCCCCCC\C=C/CCCC
Properties
Chemical formula
 C14H26O2
Molar mass 226.360 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1] 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.[2] It is a constituent of Serenoa or Saw palmetto, and appears to have activity against LNCaP prostate-cancer cells.[3]

See also

  • Cetyl myristoleate

References

  1. ^ Myristoleic acid Archived 2012-03-17 at the Wayback Machine at Lipomics.com
  2. ^ Monoenoic acids Archived 2012-10-23 at the Wayback Machine at CyberLipid.org
  3. ^ Iguchi, K; Okumura, N; Usui, S; Sajiki, H; Hirota, K; Hirano, K (Apr 2001). "Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells". The Prostate. 47 (1): 59–65. doi:10.1002/pros.1047. PMID 11304730. S2CID 946366.
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