UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Lipase-catalyzed preparation of mono- and diesters of ferulic acid
Autor/es:
GEORGINA SANDOVAL; PAULA G. QUINTANA; ALICIA BALDESSARI; ANTONIO BALLESTEROS; FRANCISCO PLOU
Revista:
BIOCATALYSIS AND BIOTRANSFORMATION
Editorial:
TAYLOR & FRANCIS LTD
Referencias:
Lugar: Londres; Año: 2015 vol. 33 p. 89 - 97
ISSN:
1024-2422
Resumen:
Lipophilic and stable derivatives of ferulic acid are required to improve its efficacy in fatty foods and to optimize its use in cosmetic and pharmaceutical preparations. We report an improved synthesis of ferulic acid monoesters (ethyl ferulate and ethyl laurate) by using immobilized lipase from Candida antarctica B (CALB) in diisopropyl ether (DIPE). Maximum yields accounted for 89% and 85% in 200 h for ethyl and lauryl ferulate, respectively. Ethyl ferulate was further acylated with vinyl esters to form ferulate diesters. 4-Acetoxy-ethyl ferulate was obtained with the immobilized lipase from Alcaligenes sp. (QLG) with 59% yield in 72 h, whereas 4-dodecanoyloxy-ethyl ferulate (a new compound) was synthesized with 52% yield in 72 h using CALB. DIPE was the best solvent for the transesterifications. Finally the anti-inflammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-inflammatory activity compared with short chain esters.