Cis-vaccenic acid

Vaccenic acid
Names


IUPAC name (E)-Octadec-11-enoic acid
Identifiers
CAS Number	693-72-1^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28727^Y
ChemSpider	4444571^Y
ECHA InfoCard	100.010.691
PubChem	5281127
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+^Y Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N^Y 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Vaccenic acid, also known as (E)-Octadec-11-enoic acid is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy products such as milk, butter, and yogurt. It is also the predominant fatty acid comprising trans fat in human milk.

Its IUPAC name is (E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).

Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat. Mammals convert it into rumenic acid, a conjugated linoleic acid, where it shows anticarcinogenic properties.

Its stereoisomer, cis-vaccenic acid, is an omega-7 fatty acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil. Its IUPAC name is (Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

A 2008 study at the University of Alberta suggests that vaccenic acid feeding in rats over 16 weeks resulted in lowered total cholesterol, lowered LDL cholesterol and lower triglyceride levels. The researchers are preparing to conduct further research, including human clinical trials.

Vaccenic acid is also found in human orbitofrontal cortex of patients with bipolar disorder and schizophrenia.

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Wikipedia