Vaccenic acid

Vaccenic acid
Names
	Preferred IUPAC name (11E)-Octadec-11-enoic acid
Identifiers
CAS Number	693-72-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28727 ;
ChemSpider	4444571 ;
ECHA InfoCard	100.010.691
PubChem CID	5281127;
UNII	GQ72OGU4EV ;
CompTox Dashboard (EPA)	DTXSID301009341 ;
	InChI InChI=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+ Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N ; 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+ Key: UWHZIFQPPBDJPM-BQYQJAHWBK;
	SMILES CCCCCC/C=C/CCCCCCCCCC(O)=O;
Properties
Chemical formula	C18H34O2
Molar mass	282.461 g/mol
Melting point	44 °C (111 °F)
Boiling point	172 °C (342 °F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]^[2] Trans fat in human milk may depend on trans fat content in food.^[3]^[4]

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).^[4]

Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid,^[5]^[6] where it shows anticarcinogenic properties.^[7]

Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.^[8] Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked,^[9] indicating that it is stockpiled similarly to omega-3 fatty acids.

^ Bowerman, Susan (May 19, 2008). "Now there are good trans fats?". Los Angeles Times.
^ Precht D, Molkentin J (August 1999). "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". Nahrung. 43 (4): 233–44. doi:10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B. PMID 10481820.
^ Friesen R, Innis SM (October 2006). "Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling". J. Nutr. 136 (10): 2558–61. doi:10.1093/jn/136.10.2558. PMID 16988126.
^ ^a ^b Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". Journal of Dairy Science. 88 (449): 449. doi:10.3168/jds.S0022-0302(05)72705-3. PMID 15653508.
^ Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived from the original on 2006-09-07. Retrieved 2007-01-15.
^ Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer. 41 (1–2): 91–7. doi:10.1080/01635581.2001.9680617. PMID 12094634. S2CID 2920114.
^ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr. 134 (10): 2698–704. doi:10.1093/jn/134.10.2698. PMID 15465769. Retrieved 2007-01-15.
^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database".
^ Bainbridge, Melissa L.; Cersosimo, Laura M.; Wright, André-Denis G.; Kraft, Jana (2016-03-01). Brockmann, Gudrun A. (ed.). "Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow". PLOS ONE. 11 (3): e0150386. Bibcode:2016PLoSO..1150386B. doi:10.1371/journal.pone.0150386. ISSN 1932-6203. PMC 4773160. PMID 26930646.

[1] Bowerman, Susan (May 19, 2008). "Now there are good trans fats?". Los Angeles Times.

[pmid10481820-2] Precht D, Molkentin J (August 1999). "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". Nahrung. 43 (4): 233–44. doi:10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B. PMID 10481820.

[pmid16988126-3] Friesen R, Innis SM (October 2006). "Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling". J. Nutr. 136 (10): 2558–61. doi:10.1093/jn/136.10.2558. PMID 16988126.

[Destaillats-4] Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". Journal of Dairy Science. 88 (449): 449. doi:10.3168/jds.S0022-0302(05)72705-3. PMID 15653508.

[Bauman-5] Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived from the original on 2006-09-07. Retrieved 2007-01-15.

[Banni-6] Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer. 41 (1–2): 91–7. doi:10.1080/01635581.2001.9680617. PMID 12094634. S2CID 2920114.

[lock-7] Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr. 134 (10): 2698–704. doi:10.1093/jn/134.10.2698. PMID 15465769. Retrieved 2007-01-15.

[sofa-8] Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database".

[9] Bainbridge, Melissa L.; Cersosimo, Laura M.; Wright, André-Denis G.; Kraft, Jana (2016-03-01). Brockmann, Gudrun A. (ed.). "Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow". PLOS ONE. 11 (3): e0150386. Bibcode:2016PLoSO..1150386B. doi:10.1371/journal.pone.0150386. ISSN 1932-6203. PMC 4773160. PMID 26930646.

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