Lipase-catalyzed monoesterification of 1-O-hexadecylglycerol in organic solvents |
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Authors: | Laura E Bertello María Laura Salto Rosa M de Lederkremer |
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Affiliation: | (1) CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
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Abstract: | A simple method is presented to esterify 1-O-hexadecyl-rac-glycerol using lipases in different organic solvents. The following fatty acids were used: C14∶0, C16∶0, C18∶0, C18∶1, and C18∶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 1H and 13C nuclear magnetic resonance spectra. |
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