Vaccenic acid

{{Short description|Trans-unsaturated fatty acid}}

{{chembox

| verifiedrevid = 477493783

| Name = Vaccenic acid

| ImageFile = Trans-vaccenic acid.svg

| ImageSize = 250px

| ImageName = Skeletal formula

| ImageFile1 = Vaccenic-acid-3D-balls.png

| ImageSize1 = 250px

| ImageName1 = Ball-and-stick model

| PIN = (11E)-Octadec-11-enoic acid

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 693-72-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GQ72OGU4EV

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28727

| PubChem = 5281127

| SMILES = CCCCCC/C=C/CCCCCCCCCC(O)=O

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444571

| InChI = 1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+

| InChIKey = UWHZIFQPPBDJPM-BQYQJAHWBK

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UWHZIFQPPBDJPM-BQYQJAHWSA-N

}}

|Section2={{Chembox Properties

| C = 18 |H = 34 |O = 2

| MolarMass = 282.461 g/mol

| Density =

| MeltingPt = {{convert|44|C|F}}

| BoilingPt = {{convert|172|C|F}}

}}

}}

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt.{{Cite web |url=https://www.latimes.com/archives/la-xpm-2008-may-19-he-eat19-story.html |title=Now there are good trans fats? |last=Bowerman |first=Susan |date=May 19, 2008 |website=Los Angeles Times}}{{Cite journal |vauthors=Precht D, Molkentin J |date=August 1999 |title=C18:1, C18:2 and C18:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids |journal=Nahrung |volume=43 |issue=4 |pages=233–44 |doi=10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B |pmid=10481820}}

Trans fat in human milk may depend on trans fat content in food.{{Cite journal |vauthors=Friesen R, Innis SM |date=October 2006 |title=Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling |journal=J. Nutr. |volume=136 |issue=10 |pages=2558–61 |doi=10.1093/jn/136.10.2558 |pmid=16988126 |doi-access=free}} Vaccenic acid was discovered in 1928 in animal fats and butter.

Mammals convert it into rumenic acid, a conjugated linoleic acid,{{Cite web |url=http://www.ansci.cornell.edu/bauman/human_health/index.htm |title=cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat |last=Bauman, Dale |archive-url=https://web.archive.org/web/20060907102559/http://www.ansci.cornell.edu/bauman/human_health/index.htm |archive-date=2006-09-07 |access-date=2007-01-15}}{{Cite journal |vauthors=Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C |year=2001 |title=Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland |journal=Nutr Cancer |volume=41 |issue=1–2 |pages=91–7 |doi=10.1080/01635581.2001.9680617 |pmid=12094634|s2cid=2920114 }}

where it shows anticarcinogenic properties.{{Cite journal |vauthors=Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C |date=October 1, 2004 |title=The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats |url=http://jn.nutrition.org/cgi/content/abstract/134/10/2698 |journal=J Nutr |volume=134 |issue=10 |pages=2698–704 |doi=10.1093/jn/134.10.2698 |pmid=15465769 |access-date=2007-01-15|doi-access=free }} Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked,{{Cite journal |last1=Bainbridge |first1=Melissa L. |last2=Cersosimo |first2=Laura M. |last3=Wright |first3=André-Denis G. |last4=Kraft |first4=Jana |date=2016-03-01 |editor-last=Brockmann |editor-first=Gudrun A. |title=Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow |journal=PLOS ONE |language=en |volume=11 |issue=3 |pages=e0150386 |doi=10.1371/journal.pone.0150386 |doi-access=free |issn=1932-6203 |pmc=4773160 |pmid=26930646|bibcode=2016PLoSO..1150386B }} indicating that it is stockpiled similarly to omega-3 fatty acids.

Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).{{Cite journal |vauthors=Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F |year=2005 |title=Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats |journal=Journal of Dairy Science |volume=88 |issue=449 |pages=449 |doi=10.3168/jds.S0022-0302(05)72705-3 |pmid=15653508 |doi-access=free}} Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.{{Cite web |url=http://www.bagkf.de/sofa/ |title=Seed Oil Fatty Acids Database |last=Federal Research Centre for Nutrition and Food - Institute for Lipid Research}} Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.