Lipase-catalyzed monoesterification of 1-O-hexadecylglycerol in organic solvents.
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 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 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.
Bertello
L E
LE
CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Salto
M L
ML
de Lederkremer
R M
RM
D002384:Catalysis; D004951:Esterification; D005227:Fatty Acids / Q000378:metabolism; D005989:Glycerides / Q000138:chemical synthesis*; D005995:Glyceryl Ethers / Q000378:metabolism*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011549:Pseudomonas / Q000201:enzymology; D012997:Solvents; D013696:Temperature
C108332:1-O-hexadecyl-2-O-hexadecanoylglycerol; D005227:Fatty Acids; D005989:Glycerides; D005995:Glyceryl Ethers; D012997:Solvents; C108333:1-O-hexadecyl-3-O-hexadecanoylglycerol; D008049:Lipase; C004348:chimyl alcohol