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Title: CHARACTERIZATION OF PRIMARY FATTY AMIDES PRODUCED BY LIPASE-CATALYZED AMIDATION OF HYDROXYLATED FATTY ACIDS

Author
item Levinson, William
item Kuo, Tsung Min
item Weisleder, David

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/17/2005
Publication Date: 7/15/2005
Citation: Levinson, W.E., Kuo, T., Weisleder, D. 2005. Characterization of primary fatty amides produced by lipase-catalyzed amidation of hydroxylated fatty acids. Journal of the American Oil Chemists' Society. 82(7): 501-504.

Interpretive Summary: Surplus vegetable oils represent attractive renewable resources for the production of useful chemicals. Previously, we investigated the reaction parameters for directly adding ammonia to the reactive terminal of common fatty acids and their derivatives by enzymatic method to form a group of new compounds called fatty amides with enhanced ability to undergo chemical reactions. In this study, we further determined the chemical structure of these new compounds by use of modern analytical instruments including gas chromatography, mass spectrometry and nuclear magnetic resonance spectroscopy that led to confirmation of the structural organization of new fatty amides. The impact of this study provides new information for scientists to develop new products from low cost vegetable oils and search for their potential new uses.

Technical Abstract: A novel hydroxylated primary fatty amide was produced from lesquerolic acid by direct amidation with ammonia catalyzed by Pseudozyma (Candida) antarctica lipase B in organic solvent. The amides of ricinoleic acid and oleic acid were also produced for comparison. The hydroxy fatty acids were transformed at comparable rates to that of oleic acid. The rate of amide formation was greater for the longer chain lesquerolic acid than that of 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 results of MS spectra, together with the proton and 13C 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.