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Synthesis of 9 Z ,11 E ‐octadecadienoic and 10 E ,12 Z ‐octadecadienoic acids, the major components of conjugated linoleic acid
Author(s) -
Chen ChienAn,
Lu Wei,
Sih Charles J.
Publication year - 1999
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-999-0436-y
Subject(s) - chemistry , conjugated linoleic acid , lipase , linoleic acid , superbase , organic chemistry , enzyme , catalysis , fatty acid
Linoleic acid was efficiently converted into the two major components of conjugated linoleic acid, 9 Z ,11 E ‐octadecadienoic ( 1a ) and 10 E ,12 Z ‐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 9 Z ,11 E 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.