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Rumenic acid

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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-Key: JBYXPOFIGCOSSB-GOJKSUSPSA-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
SMILES
  • CCCCCC\C=C/C=C/CCCCCCCC(=O)O
Properties
Chemical formula C18H32O2
Molar mass 280.452 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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. It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.

Biosynthesis and biotransformations

Rumenic acid is produced from vaccenic acid by the action of unsaturase enzymes. 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.
Lipids: fatty acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
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