Punicic acid: Difference between revisions

| 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 = C₁₈H₃₀O₂

| MolarMass = [[List of elements by atomic mass|278.43]] g/[[Mole (unit)|mol]]

| MeltingPtC = 44 to 45

| MeltingPt_notes =

}}

'''Punicic acid''' (also called '''trichosanic acid''') is a [[Polyunsaturated fat|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 [[Polyunsaturated fatty acid#Conjugated fatty acids|conjugated linolenic acid]] or CLnA; i.e. it has three [[Conjugated system|conjugated double bonds]]. It is chemically similar to the [[conjugated linoleic acid]]s, 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&mdash;a strain which becomes obese&mdash;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>

[[Image:Pomegranate.jpg|left|thumb|Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.]]{{clear left}}

* [[Punicalagin]]

* {{slink|Polyunsaturated fat|Conjugated fatty acids}}

{{reflist|colwidth=30em}}

{{Fatty acids}}

[[Category:Alkenoic acids]]

[[Category:Polyenes]]