Myristoleic acid

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] It also comprises 1.89% of the fats from the fruit of the durian species Durio graveolens.[4]

Myristoleic acid

Names
Preferred IUPAC name (9Z)-Tetradec-9-enoic acid
Other names 9-Tetradecenoic acid 9-cis-Tetradecenoic acid cis-Δ^9-Tetradecenoic acid Myristolenic acid Oleomyristic acid
Identifiers
CAS Number	544-64-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27781^N
ChemSpider	4444564^N
ECHA InfoCard	100.008.070
PubChem CID	5281119
UNII	RF23WGD123^Y
CompTox Dashboard (EPA)	DTXSID5041568
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).
N verify (what is ^YN ?)
Infobox references

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.
4. Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.