Lipase-catalyzed preparation of mono- and diesters of ferulic acid
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 Can...
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Taylor and Francis Ltd
2015
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| LEADER | 14292caa a22015137a 4500 | ||
|---|---|---|---|
| 001 | PAPER-24727 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205638.0 | ||
| 008 | 190411s2015 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84938394744 | |
| 024 | 7 | |2 cas |a diclofenac, 15307-79-6, 15307-86-5; diisopropyl ether, 108-20-3; ferulic acid, 1135-24-6, 24276-84-4; triacylglycerol lipase, 9001-62-1; vinyl acetate, 108-05-4 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BOBOE | ||
| 100 | 1 | |a Sandoval, G. | |
| 245 | 1 | 0 | |a Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| 260 | |b Taylor and Francis Ltd |c 2015 | ||
| 270 | 1 | 0 | |m Plou, F.J.; Departamento de Biocatálisis, Instituto de Catálisis y Petroleoquímica, CSIC, Cantoblanco, Marie Curie 2, Spain |
| 506 | |2 openaire |e Política editorial | ||
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| 520 | 3 | |a 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 Candida antarctica 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 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. © 2015 Informa UK, Ltd. |l eng | |
| 536 | |a Detalles de la financiación: Ministry of Education and Science, SB2010-004 | ||
| 536 | |a Detalles de la financiación: European Cooperation in Science and Technology, CM1303 | ||
| 536 | |a Detalles de la financiación: CYTED Ciencia y Tecnología para el Desarrollo | ||
| 536 | |a Detalles de la financiación: PICT 2011-00595 (Argentina) partially financed this research. Project BIO2013-48779-C4-1-R from Spanish Ministry of Economy and Competitiveness, ENZNUT network (CYTED), and COST action CM1303 on Systems Biocatalysis also supported this work. A.B. is a Research Member of CONICET (Argentina). We thank the Spanish Ministry of Education and Science for a sabbatical grant to G.S. (SB2010-004). The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the article | ||
| 593 | |a Institute of Catalysis, CSIC, Madrid, Spain | ||
| 593 | |a Laboratory of Biocatalysis, Department of Organic Chemistry and UMYMFOR, Faculty of Excat and Natural Sciences, University of Buenos Aires, Buenos Aires, Argentina | ||
| 593 | |a CIATEJ, Guadalajara, Jal, Mexico | ||
| 690 | 1 | 0 | |a ETHYL FERULATE |
| 690 | 1 | 0 | |a FERULIC ACID |
| 690 | 1 | 0 | |a FOOD ANTIOXIDANTS |
| 690 | 1 | 0 | |a HYDROXYCINNAMIC ACIDS |
| 690 | 1 | 0 | |a LIPASES |
| 690 | 1 | 0 | |a TRANSESTERIFICATION |
| 690 | 1 | 0 | |a CHAINS |
| 690 | 1 | 0 | |a ESTERS |
| 690 | 1 | 0 | |a LIPASES |
| 690 | 1 | 0 | |a TRANSESTERIFICATION |
| 690 | 1 | 0 | |a ANTI-INFLAMMATORY ACTIVITY |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA B |
| 690 | 1 | 0 | |a ETHYL FERULATE |
| 690 | 1 | 0 | |a FERULIC ACIDS |
| 690 | 1 | 0 | |a HYDROXYCINNAMIC ACIDS |
| 690 | 1 | 0 | |a PHARMACEUTICAL PREPARATIONS |
| 690 | 1 | 0 | |a SYNTHESIZED DERIVATIVES |
| 690 | 1 | 0 | |a TRANSESTERIFICATIONS |
| 690 | 1 | 0 | |a FATTY ACIDS |
| 690 | 1 | 0 | |a 4 ACETOXY ETHYL FERULATE |
| 690 | 1 | 0 | |a 4 DODECANOYLOXY ETHYL FERULATE |
| 690 | 1 | 0 | |a ANTIINFLAMMATORY AGENT |
| 690 | 1 | 0 | |a CYCLOOXYGENASE 1 |
| 690 | 1 | 0 | |a CYCLOOXYGENASE 2 |
| 690 | 1 | 0 | |a DICLOFENAC |
| 690 | 1 | 0 | |a DIISOPROPYL ETHER |
| 690 | 1 | 0 | |a DODECYL (E) 3 (4 HYDROXY 3 METHOXYPHENYL) PROP 2 ENOATE |
| 690 | 1 | 0 | |a ESTER DERIVATIVE |
| 690 | 1 | 0 | |a ETHYL (E) 3 (4 HYDROXY 3 METHOXYPHENYL) PROP 2 ENOATE |
| 690 | 1 | 0 | |a ETHYL 3 (4 ACETOXY 3 METHOXYPHENYL) PROP 2 ENOATE |
| 690 | 1 | 0 | |a ETHYL 3 (4 DODECANOYLOXY 3 METHOXYPHENYL) PROP 2 ENOATE |
| 690 | 1 | 0 | |a ETHYL FERULATE |
| 690 | 1 | 0 | |a FERULIC ACID |
| 690 | 1 | 0 | |a LAURYL FERULATE |
| 690 | 1 | 0 | |a TRIACYLGLYCEROL LIPASE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a VINYL ACETATE |
| 690 | 1 | 0 | |a ACYLATION |
| 690 | 1 | 0 | |a ALCALIGENES |
| 690 | 1 | 0 | |a ANTIINFLAMMATORY ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a ESTERIFICATION |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a TRANSESTERIFICATION |
| 690 | 1 | 0 | |a ALCALIGENES SP. |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 700 | 1 | |a Quintana, P.G. | |
| 700 | 1 | |a Baldessari, A. | |
| 700 | 1 | |a Ballesteros, A.O. | |
| 700 | 1 | |a Plou, F.J. | |
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