Punicic acid

Punicic acid

Names
IUPAC name 9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Identifiers
CAS Number	544-72-9
3D model (Jmol)	Interactive image
ChEBI	CHEBI:8638
ChemSpider	4444570
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 cis-9, trans-11, cis-13. 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. It has been erroneous classified as "n-5" or "omega-5" polyunsaturated fatty acid because the last double bond is located at 5 carbon from the terminal "omega" carbon, however the "n-x" notation can only be applied to all cis, methylene interrupted polyunsaturated fatty acids. 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.