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. Trans fat in human milk may depend on trans fat content in food. Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid, where it shows anticarcinogenic properties. Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked, 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). Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil. Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.