Rumenic acid

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 280.452 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans fatty acid. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer et al. in 1998.[1] It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.[2]

Biosynthesis and biotransformations

Rumenic acid is produced from vaccenic acid by the action of unsaturase enzymes.[3] Rumenic acid is converted back to vaccenic acid en route to stearic acid

Further reading

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. PMID 15653508.

References

  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. PMID 9727617. S2CID 10693714.
  2. ^ Cyberlipid. "Polyenoic Fatty Acids". Retrieved 2007-01-17.
  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. PMID 12197992.

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