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Lipase‐catalyzed monoesterification of 1‐ O ‐hexadecylglycerol in organic solvents
Author(s) -
Bertello Laura E.,
Salto María Laura,
Lederkremer Rosa M.
Publication year - 1997
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/s11745-997-0117-x
Subject(s) - chemistry , chromatography , yield (engineering) , lipase , glyceride , column chromatography , thin layer chromatography , high performance liquid chromatography , dichloromethane , fatty acid , catalysis , hydrophilic interaction chromatography , organic chemistry , solvent , enzyme , materials science , metallurgy
A simple method is presented to esterify 1‐ O ‐hexadecyl‐ rac ‐glycerol using lipases in different organic solvents. The following fatty acids were used: C 14∶0 , C 16∶0 , C 18∶0 , C 18∶1 , and C 18∶2 . Monoesterification was achieved by using a limiting amount of the fatty acid. Both the 1‐ O ‐hexadecyl‐3‐ O ‐acylglycerol and the 2‐ O ‐acylglycerol were obtained in a total yield of 75% and a ratio of 7∶1 in dichloromethane after 3 d. Chromatographic data for the monoesters, useful for the identification of the natural products, are given (gas‐liquid chromatography, thin‐layer chromatography, reverse‐phase thin‐layer chromatography). The structure was confirmed by a chemical synthesis of 1‐ O ‐hexadecyl‐2‐ O ‐hexadecanoylglycerol. The 3‐ O ‐glyceride was also formed by acyl migration, as the minor component. The monoesters were separated by column chromatography and characterized by 1 H and 13 C nuclear magnetic resonance spectra.