Lipase-catalyzed preparation of mono- and diesters of ferulic acid

Autores
Sandoval, Georgina; Quintana, Paula Gabriela; Baldessari, Alicia; Ballesteros, Antonio O.; Plou, Francisco J.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Lipophilic and stable derivatives of ferulic acid are required to improve its effi cacy 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 transesterifi cations. Finally, the anti-infl ammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-infl ammatory activity compared with short-chain esters.
Fil: Sandoval, Georgina. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Ballesteros, Antonio O.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
Fil: Plou, Francisco J.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
Materia
Ferulic Acid Esters
Lipase-Catalyzed
Synthesis
Anti-Inflammatory Activity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/18714
Acceder
id CONICETDig_96498428d41fd431b807066fedad70a8
oai_identifier_str oai:ri.conicet.gov.ar:11336/18714
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Lipase-catalyzed preparation of mono- and diesters of ferulic acidSandoval, GeorginaQuintana, Paula GabrielaBaldessari, AliciaBallesteros, Antonio O.Plou, Francisco J.Ferulic Acid EstersLipase-CatalyzedSynthesisAnti-Inflammatory Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Lipophilic and stable derivatives of ferulic acid are required to improve its effi cacy 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 transesterifi cations. Finally, the anti-infl ammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-infl ammatory activity compared with short-chain esters.Fil: Sandoval, Georgina. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; EspañaFil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Ballesteros, Antonio O.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; EspañaFil: Plou, Francisco J.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; EspañaTaylor & Francis2015-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/18714Sandoval, Georgina; Quintana, Paula Gabriela; Baldessari, Alicia; Ballesteros, Antonio O.; Plou, Francisco J.; Lipase-catalyzed preparation of mono- and diesters of ferulic acid ; Taylor & Francis; Biocatalysis and Biotransformation; 33; 2; 7-2015; 89-971024-24221029-244CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3109/10242422.2015.1060228info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/full/10.3109/10242422.2015.1060228info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:37:53Zoai:ri.conicet.gov.ar:11336/18714instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:37:54.233CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Lipase-catalyzed preparation of mono- and diesters of ferulic acid
title Lipase-catalyzed preparation of mono- and diesters of ferulic acid
spellingShingle Lipase-catalyzed preparation of mono- and diesters of ferulic acid
Sandoval, Georgina
Ferulic Acid Esters
Lipase-Catalyzed
Synthesis
Anti-Inflammatory Activity
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
dc.creator.none.fl_str_mv Sandoval, Georgina
Quintana, Paula Gabriela
Baldessari, Alicia
Ballesteros, Antonio O.
Plou, Francisco J.
author Sandoval, Georgina
author_facet Sandoval, Georgina
Quintana, Paula Gabriela
Baldessari, Alicia
Ballesteros, Antonio O.
Plou, Francisco J.
author_role author
author2 Quintana, Paula Gabriela
Baldessari, Alicia
Ballesteros, Antonio O.
Plou, Francisco J.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Ferulic Acid Esters
Lipase-Catalyzed
Synthesis
Anti-Inflammatory Activity
topic Ferulic Acid Esters
Lipase-Catalyzed
Synthesis
Anti-Inflammatory Activity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Lipophilic and stable derivatives of ferulic acid are required to improve its effi cacy 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 transesterifi cations. Finally, the anti-infl ammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-infl ammatory activity compared with short-chain esters.
Fil: Sandoval, Georgina. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Ballesteros, Antonio O.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
Fil: Plou, Francisco J.. Consejo Superior de Investigaciones Científicas. Instituto de Catalisis y Petroleoquímica; España
description Lipophilic and stable derivatives of ferulic acid are required to improve its effi cacy 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 transesterifi cations. Finally, the anti-infl ammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-infl ammatory activity compared with short-chain esters.
publishDate 2015
dc.date.none.fl_str_mv 2015-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/18714
Sandoval, Georgina; Quintana, Paula Gabriela; Baldessari, Alicia; Ballesteros, Antonio O.; Plou, Francisco J.; Lipase-catalyzed preparation of mono- and diesters of ferulic acid ; Taylor & Francis; Biocatalysis and Biotransformation; 33; 2; 7-2015; 89-97
1024-2422
1029-244
CONICET Digital
CONICET
url http://hdl.handle.net/11336/18714
identifier_str_mv Sandoval, Georgina; Quintana, Paula Gabriela; Baldessari, Alicia; Ballesteros, Antonio O.; Plou, Francisco J.; Lipase-catalyzed preparation of mono- and diesters of ferulic acid ; Taylor & Francis; Biocatalysis and Biotransformation; 33; 2; 7-2015; 89-97
1024-2422
1029-244
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3109/10242422.2015.1060228
info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/full/10.3109/10242422.2015.1060228
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis
publisher.none.fl_str_mv Taylor & Francis
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1846082854983827456
score 13.22299

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