Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity

A series of novel fatty acid derivatives of pyridoxine, one of the three members of the vitamin B6 group, has been prepared. These products were obtained using an enzymatic approach. Several lipases catalyzed esterification and transesterification reactions of pyridoxine with carboxylic acid or alky...

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Autor principal: Baldessari, A.
Otros Autores: Mangone, C.P
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
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Acceso en línea:Registro en Scopus
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040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a BOBOE 
100 1 |a Baldessari, A. 
245 1 0 |a Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity 
260 |c 2002 
270 1 0 |m Baldessari, A.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Angerer, P., Von Schacky, C., ω-3 Polyunsaturated fatty acids and the cardiovascular system (2000) Curr. Opin. Lipidol., 11, pp. 57-63 
504 |a Baldessari, A., Mangone, C.P., (2000) Patent Pending, INPI, AR 00 01 04147 
504 |a Baldessari, A., Mangone, C.P., Gros, E.G., Lipase-catalyzed acylation and deacylation reactions of pyridoxine, member of vitamin B6 group (1998) Helv. Chim. Acta, 81, pp. 2407-2413 
504 |a Becher, P., (1966) Emulsions: Theory and Practice, , (Marcel Dekker, New York) 
504 |a Bowen, W.H., Food components and caries (1994) Adv. Dent. Res., 8, pp. 215-220 
504 |a Brown, L., Johnston, A., Sukling, C.J., Halling, P.J., Valivety, R.H., Pyridoxal derivatives as probes for water concentration in non-aqueous solvents (1993) J. Chem. Soc. Perkin Trans., 1, pp. 2777-2780 
504 |a (1997) Physical Properties! Pro™, Computational Chemistry Program, , revision (1997) (Fairfield, California) 
504 |a Driskell, J.A., Vitamin B6 requirements of humans (1994) Nutr. Res., 14, pp. 293-324 
504 |a Faber, K., (2000) Biotransformations in Organic Chemistry, A Textbook, 4th Ed, , (Springer, Berlin) 
504 |a Griffin, W.C., Classification of surface-active agents by HLB (1949) J. Soc. Cosmet. Chem., 1, pp. 311-316 
504 |a Korytnyk, W., Paul, B., Acyl migration and selective esterification in pyridoxol (1967) J. Org. Chem., 32, pp. 3791-3796 
504 |a Simopoulos, A.P., New products from the agri-food industry: The return of ω-3 fatty acids into the food supply (1999) Lipids, 34 (SUPPL.), pp. S297-S301 
504 |a Snider, B., Dietman, D.F., Pyridoxine therapy for acne flare (1974) Arch. Dermatol., 110, pp. 130-131 
504 |a Wong, C.H., Whitesides, G.M., Enzymes in synthetic organic chemistry (1994) Tetrahedron Organic Chemistry Series, 12. , In: Baldwin, J.E. and Magnus, P.D., eds; (Elsevier Science, Oxford) 
504 |a Wyatt, K.M., Efficacy of vitamin B6 in the treatment of premenstrual syndrome: Systematic review (1999) Br. Med. J., 318, pp. 1375-1381 
520 3 |a A series of novel fatty acid derivatives of pyridoxine, one of the three members of the vitamin B6 group, has been prepared. These products were obtained using an enzymatic approach. Several lipases catalyzed esterification and transesterification reactions of pyridoxine with carboxylic acid or alkyl carboxylates showed a remarkable regioselective behavior; only monoacyl derivatives were obtained. The surfactant activity, composition and clean enzymatic methodology applied in the preparation of these products make them useful as ingredients in cosmetic and pharmaceutical formulations or food additives.  |l eng 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: Our thanks to UMYMFOR and LANAIS-EMAR for the CG analysis and spectra. We are indebted to CONICET for partial financial support. 
593 |a Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
690 1 0 |a ENZYME-CATALYZED 
690 1 0 |a FATTY ACIDS 
690 1 0 |a PYRIDOXINE 
690 1 0 |a SURFACTANTS 
690 1 0 |a BIOSYNTHESIS 
690 1 0 |a CARBOXYLIC ACIDS 
690 1 0 |a DERIVATIVES 
690 1 0 |a DRUG PRODUCTS 
690 1 0 |a ENZYMES 
690 1 0 |a ESTERIFICATION 
690 1 0 |a FATTY ACIDS 
690 1 0 |a FOOD ADDITIVES 
690 1 0 |a SURFACE ACTIVE AGENTS 
690 1 0 |a VITAMINS 
690 1 0 |a REGIOSELECTIVE 
690 1 0 |a NITROGEN COMPOUNDS 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYL 13 DOCOSENOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYL 5,8,11,14 EICOSATETRAENOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYL 9 OCTADECANOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYL 9,12 OCTADECANOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYL 9,12,15 OCTADECATRIENOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYLEICOSANOIC ACID 
690 1 0 |a (5 HYDROXY 4 HYDROXYMETHYL 6 METHYLPYRIDIN 3 YL)METHYLOCTADECANOIC ACID 
690 1 0 |a CARBOXYLIC ACID 
690 1 0 |a FATTY ACID DERIVATIVE 
690 1 0 |a FOOD ADDITIVE 
690 1 0 |a PYRIDOXINE DERIVATIVE 
690 1 0 |a SURFACTANT 
690 1 0 |a TRIACYLGLYCEROL LIPASE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ACYLATION 
690 1 0 |a ARTICLE 
690 1 0 |a CATALYSIS 
690 1 0 |a COSMETIC INDUSTRY 
690 1 0 |a DRUG ACTIVITY 
690 1 0 |a DRUG FORMULATION 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a ENZYMATIC ASSAY 
690 1 0 |a ENZYME SUBSTRATE 
690 1 0 |a NONHUMAN 
690 1 0 |a PHARMACEUTICAL ENGINEERING 
690 1 0 |a SWINE 
690 1 0 |a SUS SCROFA 
650 1 7 |2 spines  |a PANCREAS 
700 1 |a Mangone, C.P. 
773 0 |d 2002  |g v. 20  |h pp. 275-279  |k n. 4  |p Biocatal. Biotransform.  |x 10242422  |w (AR-BaUEN)CENRE-3908  |t Biocatalysis and Biotransformation 
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856 4 0 |u https://doi.org/10.1080/10242420290004910  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_10242422_v20_n4_p275_Baldessari  |y Handle 
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