Synthesis of 9Z,11E-octadecadienoic and 10E,12Z-octadecadienoic acids, the major components of conjugated linoleic acid.
Linoleic acid was efficiently converted into the two major components of conjugated linoleic acid, 9Z,11E-octadecadienoic (1a) and 10E,12Z-octadecadienoic acid (1b) using either the superbase (n-butyllithium/potassium tert-butoxide) or by simply refluxing with KOH in 1-butanol. In turn, 1a and 1b were separated from each other using the lipase from Aspergillus niger via stereoselective esterification in 1-butanol. This enzyme has a preference for the 9Z,11E isomer, 1a, and has excellent selectivity. This method has allowed the ready preparation of gram quantities of 1a and 1b in their highly purified forms, which are not readily accessible by current methods.
Chen
C A
CA
School of Pharmacy, University of Wisconsin, Madison 53706-1515, USA.
Lu
W
W
Sih
C J
CJ
D000818:Animals; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000302:isolation & purification; D008041:Linoleic Acids / Q000737:chemistry*; D008049:Lipase; D008460:Meat / Q000032:analysis*; D008722:Methods; D013237:Stereoisomerism
D005231:Fatty Acids, Unsaturated; D008041:Linoleic Acids; C027369:octadecadienoic acid; D008049:Lipase