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...
Guardado en:
| Publicado: |
2015
|
|---|---|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v33_n2_p89_Sandoval http://hdl.handle.net/20.500.12110/paper_10242422_v33_n2_p89_Sandoval |
| Aporte de: |
| id |
paper:paper_10242422_v33_n2_p89_Sandoval |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_10242422_v33_n2_p89_Sandoval2023-06-08T16:00:13Z Lipase-catalyzed preparation of mono- and diesters of ferulic acid Ethyl ferulate ferulic acid food antioxidants hydroxycinnamic acids lipases transesterification Chains Esters Lipases Transesterification Anti-inflammatory activity Candida antarctica B Ethyl ferulate Ferulic acids Hydroxycinnamic acids Pharmaceutical preparations Synthesized derivatives Transesterifications Fatty acids 4 acetoxy ethyl ferulate 4 dodecanoyloxy ethyl ferulate antiinflammatory agent cyclooxygenase 1 cyclooxygenase 2 diclofenac diisopropyl ether dodecyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ester derivative ethyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 acetoxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 dodecanoyloxy 3 methoxyphenyl) prop 2 enoate ethyl ferulate ferulic acid lauryl ferulate triacylglycerol lipase unclassified drug vinyl acetate acylation Alcaligenes antiinflammatory activity Article Candida antarctica catalysis controlled study drug synthesis esterification in vitro study nonhuman transesterification Alcaligenes sp. Candida antarctica 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. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v33_n2_p89_Sandoval http://hdl.handle.net/20.500.12110/paper_10242422_v33_n2_p89_Sandoval |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Ethyl ferulate ferulic acid food antioxidants hydroxycinnamic acids lipases transesterification Chains Esters Lipases Transesterification Anti-inflammatory activity Candida antarctica B Ethyl ferulate Ferulic acids Hydroxycinnamic acids Pharmaceutical preparations Synthesized derivatives Transesterifications Fatty acids 4 acetoxy ethyl ferulate 4 dodecanoyloxy ethyl ferulate antiinflammatory agent cyclooxygenase 1 cyclooxygenase 2 diclofenac diisopropyl ether dodecyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ester derivative ethyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 acetoxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 dodecanoyloxy 3 methoxyphenyl) prop 2 enoate ethyl ferulate ferulic acid lauryl ferulate triacylglycerol lipase unclassified drug vinyl acetate acylation Alcaligenes antiinflammatory activity Article Candida antarctica catalysis controlled study drug synthesis esterification in vitro study nonhuman transesterification Alcaligenes sp. Candida antarctica |
| spellingShingle |
Ethyl ferulate ferulic acid food antioxidants hydroxycinnamic acids lipases transesterification Chains Esters Lipases Transesterification Anti-inflammatory activity Candida antarctica B Ethyl ferulate Ferulic acids Hydroxycinnamic acids Pharmaceutical preparations Synthesized derivatives Transesterifications Fatty acids 4 acetoxy ethyl ferulate 4 dodecanoyloxy ethyl ferulate antiinflammatory agent cyclooxygenase 1 cyclooxygenase 2 diclofenac diisopropyl ether dodecyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ester derivative ethyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 acetoxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 dodecanoyloxy 3 methoxyphenyl) prop 2 enoate ethyl ferulate ferulic acid lauryl ferulate triacylglycerol lipase unclassified drug vinyl acetate acylation Alcaligenes antiinflammatory activity Article Candida antarctica catalysis controlled study drug synthesis esterification in vitro study nonhuman transesterification Alcaligenes sp. Candida antarctica Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| topic_facet |
Ethyl ferulate ferulic acid food antioxidants hydroxycinnamic acids lipases transesterification Chains Esters Lipases Transesterification Anti-inflammatory activity Candida antarctica B Ethyl ferulate Ferulic acids Hydroxycinnamic acids Pharmaceutical preparations Synthesized derivatives Transesterifications Fatty acids 4 acetoxy ethyl ferulate 4 dodecanoyloxy ethyl ferulate antiinflammatory agent cyclooxygenase 1 cyclooxygenase 2 diclofenac diisopropyl ether dodecyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ester derivative ethyl (e) 3 (4 hydroxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 acetoxy 3 methoxyphenyl) prop 2 enoate ethyl 3 (4 dodecanoyloxy 3 methoxyphenyl) prop 2 enoate ethyl ferulate ferulic acid lauryl ferulate triacylglycerol lipase unclassified drug vinyl acetate acylation Alcaligenes antiinflammatory activity Article Candida antarctica catalysis controlled study drug synthesis esterification in vitro study nonhuman transesterification Alcaligenes sp. Candida antarctica |
| description |
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. |
| title |
Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| title_short |
Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| title_full |
Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| title_fullStr |
Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| title_full_unstemmed |
Lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| title_sort |
lipase-catalyzed preparation of mono- and diesters of ferulic acid |
| publishDate |
2015 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v33_n2_p89_Sandoval http://hdl.handle.net/20.500.12110/paper_10242422_v33_n2_p89_Sandoval |
| _version_ |
1768542748172877824 |