Punicic acid

Punicic acid

Names
IUPAC name 9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Identifiers
CAS Number	544-72-9
ChEBI	CHEBI:8638
ChemSpider	4444570
Jmol interactive 3D	Image
PubChem	5281126
InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5-,8-7+,10-9- Key: CUXYLFPMQMFGPL-BGDVVUGTSA-N InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5-,8-7+,10-9- Key: CUXYLFPMQMFGPL-BGDVVUGTBE
SMILES CCCC\C=C/C=C/C=C\CCCCCCCC(=O)O
Properties
Chemical formula	C18H30O2
Molar mass	278.43 g/mol
Melting point	44 to 45 °C (111 to 113 °F; 317 to 318 K)
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

Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 (n-5). It is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil. It is also found in the seed oils of snake gourd.^[1]

Punicic acid is a conjugated linolenic acid or CLnA; i.e. it has three conjugated double bonds. It is chemically similar to the conjugated linoleic acids, or CLA, which have two. In lab rats, it was found that punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).^[2] In vitro, it shows anticancer activity against prostate cancer cells.^[3] OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.^[4]

Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.

See also

• Polyunsaturated fatty acids—Conjugated fatty acids

References

1. Cyberlipid. "POLYENOIC FATTY ACIDS". Retrieved 2007-01-11.
2. Tsuzuki T, Kawakami Y, Abe R (1 August 2006). "Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid". J Nutr 136 (8): 2153–9. PMID 16857834. Retrieved 2007-01-23.
3. Lansky E, Harrison G, Froom P, Jiang W (2005). "Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel". Invest New Drugs 23 (2): 121–2. doi:10.1007/s10637-005-5856-7. PMID 15744587.
4. Arao K, Wang Y, Inoue N, Hirata J, Cha J, Nagao K, Yanagita T (2004). "Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats". Lipids Health Dis 3: 24. doi:10.1186/1476-511X-3-24. PMC 534798. PMID 15533261. Retrieved 2007-01-23.