Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

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.

Registro:

Documento: Artículo
Título:Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity
Autor:Baldessari, A.; Mangone, C.P.
Filiación:Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:Enzyme-catalyzed; Fatty acids; Pyridoxine; Surfactants; Biosynthesis; Carboxylic acids; Derivatives; Drug products; Enzymes; Esterification; Fatty acids; Food additives; Surface active agents; Vitamins; Regioselective; Nitrogen compounds; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 13 docosenoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 5,8,11,14 eicosatetraenoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9 octadecanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9,12 octadecanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9,12,15 octadecatrienoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyleicosanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyloctadecanoic acid; carboxylic acid; fatty acid derivative; food additive; pyridoxine derivative; surfactant; triacylglycerol lipase; unclassified drug; acylation; article; catalysis; cosmetic industry; drug activity; drug formulation; drug synthesis; enzymatic assay; enzyme substrate; nonhuman; pancreas; pharmaceutical engineering; swine; Sus scrofa
Año:2002
Volumen:20
Número:4
Página de inicio:275
Página de fin:279
DOI: http://dx.doi.org/10.1080/10242420290004910
Título revista:Biocatalysis and Biotransformation
Título revista abreviado:Biocatal. Biotransform.
ISSN:10242422
CODEN:BOBOE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v20_n4_p275_Baldessari

Referencias:

  • Angerer, P., Von Schacky, C., ω-3 Polyunsaturated fatty acids and the cardiovascular system (2000) Curr. Opin. Lipidol., 11, pp. 57-63
  • Baldessari, A., Mangone, C.P., (2000) Patent Pending, INPI, AR 00 01 04147
  • 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
  • Becher, P., (1966) Emulsions: Theory and Practice, , (Marcel Dekker, New York)
  • Bowen, W.H., Food components and caries (1994) Adv. Dent. Res., 8, pp. 215-220
  • 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
  • (1997) Physical Properties! Pro™, Computational Chemistry Program, , revision (1997) (Fairfield, California)
  • Driskell, J.A., Vitamin B6 requirements of humans (1994) Nutr. Res., 14, pp. 293-324
  • Faber, K., (2000) Biotransformations in Organic Chemistry, A Textbook, 4th Ed, , (Springer, Berlin)
  • Griffin, W.C., Classification of surface-active agents by HLB (1949) J. Soc. Cosmet. Chem., 1, pp. 311-316
  • Korytnyk, W., Paul, B., Acyl migration and selective esterification in pyridoxol (1967) J. Org. Chem., 32, pp. 3791-3796
  • 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
  • Snider, B., Dietman, D.F., Pyridoxine therapy for acne flare (1974) Arch. Dermatol., 110, pp. 130-131
  • 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)
  • Wyatt, K.M., Efficacy of vitamin B6 in the treatment of premenstrual syndrome: Systematic review (1999) Br. Med. J., 318, pp. 1375-1381

Citas:

---------- APA ----------
Baldessari, A. & Mangone, C.P. (2002) . Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatalysis and Biotransformation, 20(4), 275-279.
http://dx.doi.org/10.1080/10242420290004910
---------- CHICAGO ----------
Baldessari, A., Mangone, C.P. "Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity" . Biocatalysis and Biotransformation 20, no. 4 (2002) : 275-279.
http://dx.doi.org/10.1080/10242420290004910
---------- MLA ----------
Baldessari, A., Mangone, C.P. "Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity" . Biocatalysis and Biotransformation, vol. 20, no. 4, 2002, pp. 275-279.
http://dx.doi.org/10.1080/10242420290004910
---------- VANCOUVER ----------
Baldessari, A., Mangone, C.P. Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatal. Biotransform. 2002;20(4):275-279.
http://dx.doi.org/10.1080/10242420290004910