Punicic acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 428799343

| Name = Punicic acid

| ImageFile = Punicic acid.svg

| ImageSize =

| ImageName = Punicic acid

| PIN = (9Z,11E,13Z)-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 = C₁₈H₃₀O₂

| MolarMass = 278.43 g/mol

| MeltingPtC = 44 to 45

| MeltingPt_notes =

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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.{{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}}

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).

{{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}} In vitro, it shows anti-invasive activity against prostate cancer cells.{{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 }} OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.{{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 }}

Image:Pomegranate.jpg{{clear left}}