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Characterization of primary fatty amides produced by lipase‐catalyzed amidation of hydroxylated fatty acids
Author(s) -
Levinson William E.,
Min Kuo Tsung,
Weisleder David
Publication year - 2005
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-005-1100-7
Subject(s) - ricinoleic acid , chemistry , oleic acid , amide , lipase , candida antarctica , organic chemistry , fatty acid , catalysis , castor oil , stereochemistry , enzyme , biochemistry
Abstract A novel hydroxylated primary fatty amide was produced from lesquerolic acid by direct amidation with ammonia catalyzed by immobilized Pseudozyma (Candida) antarctica lipase B (Novozym 435) in organic solvent. The amides of ricinoleic acid and oleic acid were also produced for comparison. The hydroxy FA were transformed at comparable rates to that of oleic acid. The rate of amide formation was greater for the longerchain lesquerolic acid than for ricinoleic acid. All products exhibited characteristic primary‐amide mass spectrum peaks with a base peak at m/z 59 and a strong ion fragment at m/z 72. Other peaks present are consistent with cleavage on either side of the hydroxyl position. The mass spectra, together with 1 H and 13 C NMR data, suggest that the products of lipase‐catalyzed direct amidation of ricinoleic acid and lesquerolic acid are 12‐hydroxy‐9( Z )‐octadecenamide and 14‐hydroxy‐11( Z )‐eicosenamide, respectively.