Lipase-catalyzed preparation of mono- and diesters of ferulic acid. (April 2015)

• Record Type: Journal Article
• Authors: Sandoval, Georgina; Quintana, Paula G.; Baldessari, Alicia; Ballesteros, Antonio O.; Plou, Francisco J.
• Is Part Of: Biocatalysis and biotransformation. Volume 33:Number 2(2015)
• Page Start: 89
• Page End: 97
• Publication Date: 2015-04
• Subjects: Enzymes -- Biotechnology -- Periodicals; Enzymes -- Industrial applications -- Periodicals; Biotransformation (Metabolism) -- Periodicals; 660.63
• DOI: 10.3109/10242422.2015.1060228
• Languages: English
• ISSNs: 1024-2422

Abstract

<abstract> <title>Abstract</title> <p>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 lauryl ferulate) using immobilized lipase from <italic>Candida antarctica</italic> B (CALB) in diisopropyl ether (DIPE). Maximum yields were 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 <italic>Alcaligenes</italic> 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 <italic>in vitro</italic>; the compounds bearing a dodecyl chain showed improved anti-inflammatory activity compared with short-chain esters.</p> </abstract>