{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428799343 | Name = Punicic acid | ImageFile = Punicic acid.svg | ImageSize = | ImageName = Punicic acid | PIN = (9''Z'',11''E'',13''Z'')-Octadeca-9,11,13-trienoic acid |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 544-72-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = VFQ03H211O | SMILES = CCCC\C=C/C=C/C=C\CCCCCCCC(=O)O | PubChem = 5281126 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4444570 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 8638 | 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- | InChIKey = CUXYLFPMQMFGPL-BGDVVUGTBE | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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- | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CUXYLFPMQMFGPL-BGDVVUGTSA-N }} |Section2={{Chembox Properties | Formula = C<sub>18</sub>H<sub>30</sub>O<sub>2</sub> | MolarMass = 278.43 g/mol | MeltingPtC = 44 to 45 | MeltingPt_notes = }} }}
'''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 has also been found in the seed oils of snake gourd.<ref>{{cite web|author=Cyberlipid|url=http://www.cyberlipid.org/fa/acid0003.htm|access-date=2007-01-11|title=POLYENOIC FATTY ACIDS|archive-url=https://web.archive.org/web/20180930034042/http://www.cyberlipid.org/fa/acid0003.htm|archive-date=2018-09-30|url-status=dead}}</ref>
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 also been classified as an "n-5" or "omega-5" polyunsaturated fatty acid. In lab rats, punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).<ref name=Tsuzuki> {{cite journal| journal=J Nutr|date=1 August 2006|volume=136|issue=8|pages=2153–9| access-date= 2007-01-23|title=Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid|vauthors=Tsuzuki T, Kawakami Y, Abe R |doi=10.1093/jn/136.8.2153|url=http://jn.nutrition.org/cgi/content/abstract/136/8/2153|pmid=16857834|doi-access=free}}</ref> ''In vitro'', it shows anti-invasive activity against prostate cancer cells.<ref name=Lansky>{{cite journal |vauthors=Lansky E, Harrison G, Froom P, Jiang W |title=Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel |journal=Invest New Drugs |volume=23 |issue=2 |pages=121–2 |year=2005 |pmid=15744587|doi=10.1007/s10637-005-5856-7|s2cid=5867887 }}<!--| accessdate= 2007-01-23 --></ref> OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.<ref>{{cite journal |vauthors=Arao K, Wang Y, Inoue N, Hirata J, Cha J, Nagao K, Yanagita T |title=Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats |journal=Lipids Health Dis |volume=3 |pages=24 |year= 2004|pmid=15533261|doi=10.1186/1476-511X-3-24 |pmc=534798 |doi-access=free }}</ref> left|thumb|Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.{{clear left}}
==See also== * Punicalagin * {{slink|Polyunsaturated fat|Conjugated fatty acids}}
==References== {{reflist|colwidth=30em}} {{Fatty acids}} {{DEFAULTSORT:Punicic Acid}} Category:Fatty acids Category:Alkenoic acids Category:Polyenes