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: 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.
Registro:
Documento: |
Artículo
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Título: | Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents |
Autor: | Bertello, L.E.; Salto, M.L.; De Lederkremer, R.M. |
Filiación: | CIHIDECAR, Depto. de Quim. Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina
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Palabras clave: | 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 |
Año: | 1997
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Volumen: | 32
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Número: | 8
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Página de inicio: | 907
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Página de fin: | 911
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DOI: |
http://dx.doi.org/10.1007/s11745-997-0117-x |
Título revista: | Lipids
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Título revista abreviado: | LIPIDS
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ISSN: | 00244201
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CODEN: | LPDSA
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CAS: | 1-O-hexadecyl-2-O-hexadecanoylglycerol; 1-O-hexadecyl-3-O-hexadecanoylglycerol, 17810-56-9; chimyl alcohol, 53584-29-5; Fatty Acids; Glycerides; Glyceryl Ethers; Lipase, EC 3.1.1.3; Solvents
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v32_n8_p907_Bertello |
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Citas:
---------- APA ----------
Bertello, L.E., Salto, M.L. & De Lederkremer, R.M.
(1997)
. Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents. Lipids, 32(8), 907-911.
http://dx.doi.org/10.1007/s11745-997-0117-x---------- CHICAGO ----------
Bertello, L.E., Salto, M.L., De Lederkremer, R.M.
"Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents"
. Lipids 32, no. 8
(1997) : 907-911.
http://dx.doi.org/10.1007/s11745-997-0117-x---------- MLA ----------
Bertello, L.E., Salto, M.L., De Lederkremer, R.M.
"Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents"
. Lipids, vol. 32, no. 8, 1997, pp. 907-911.
http://dx.doi.org/10.1007/s11745-997-0117-x---------- VANCOUVER ----------
Bertello, L.E., Salto, M.L., De Lederkremer, R.M. Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents. LIPIDS. 1997;32(8):907-911.
http://dx.doi.org/10.1007/s11745-997-0117-x