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: 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...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Bertello, Laura Elena, Salto, María Laura, Muchnik de Lederkremer, Rosa María
Publicado:	1997
Materias:	chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v32_n8_p907_Bertello http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00244201_v32_n8_p907_Bertello
record_format	dspace
spelling	paper:paper_00244201_v32_n8_p907_Bertello2023-06-08T14:52:27Z Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents Bertello, Laura Elena Salto, María Laura Muchnik de Lederkremer, Rosa María chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature 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 1H and 13C nuclear magnetic resonance spectra. Fil:Bertello, L.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Salto, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v32_n8_p907_Bertello http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature
spellingShingle	chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature Bertello, Laura Elena Salto, María Laura Muchnik de Lederkremer, Rosa María Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
topic_facet	chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature
description	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 1H and 13C nuclear magnetic resonance spectra.
author	Bertello, Laura Elena Salto, María Laura Muchnik de Lederkremer, Rosa María
author_facet	Bertello, Laura Elena Salto, María Laura Muchnik de Lederkremer, Rosa María
author_sort	Bertello, Laura Elena
title	Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_short	Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_full	Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_fullStr	Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_full_unstemmed	Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_sort	lipase-catalyzed monoesterification of 1-o-hexadecylglycerol in organic solvents
publishDate	1997
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v32_n8_p907_Bertello http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
work_keys_str_mv	AT bertellolauraelena lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents AT saltomarialaura lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents AT muchnikdelederkremerrosamaria lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents
_version_	1768545634754756608

Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents

Ejemplares similares