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Rumenic acid

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Rumenic acid
Rumenic acid
Names
Preferred IUPAC name
(9Z,11E)-Octadeca-9,11-dienoic acid
Other names
Bovinic acid; C9-T11 acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9-☒N
    Key: JBYXPOFIGCOSSB-GOJKSUSPSA-N☒N
  • InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9-
    Key: JBYXPOFIGCOSSB-GOJKSUSPBK
  • CCCCCC\C=C/C=C/CCCCCCCC(=O)O
Properties
C18H32O2
Molar mass 280.452g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Rumenic acid,also known asbovinic acid,is aconjugated linoleic acid(CLA) found in the fat ofruminantsand indairy products.It is anOmega -7trans fatty acid.Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Krameret al.in 1998.[1]It can be considered as the principal dietary form, accounting for as much as 85-90% of the totalCLAcontent in dairy products.[2]

Biosynthesis and biotransformations[edit]

Rumenic acid is produced fromvaccenic acidby the action of unsaturase enzymes.[3]Rumenic acid is converted back to vaccenic acid en route tostearic acid

Further reading[edit]

F. Destaillats; E. Buyukpamukcu; P.-A. Golay; F. Dionisi & F. Giuffrida (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.PMID15653508.

References[edit]

  1. ^Kramer J, Parodi P, Jensen R, Mossoba M, Yurawecz M, Adlof R (1998). "Rumenic acid: a proposed common name for the major conjugated linoleic acid isomer found in natural products".Lipids.33(8): 835.doi:10.1007/s11745-998-0279-6.PMID9727617.S2CID10693714.
  2. ^Cyberlipid."Polyenoic Fatty Acids".Retrieved2007-01-17.
  3. ^Turpeinen, Anu M.; Mutanen, Marja; Aro, Antti; Salminen, Irma; Basu, Samar; Palmquist, Donald L.; Griinari, J Mikko (2002)."Bioconversion of vaccenic acid to conjugated linoleic acid in humans".The American Journal of Clinical Nutrition.76(3): 504–510.doi:10.1093/ajcn/76.3.504.PMID12197992.