Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis

Autores
Cavaca, Lídia A. S.; Rodrigues, Catarina A. B.; Simeonov, Svilen P.; Gomes, Rafael F. A.; Coelho, Jaime A. S.; Romanelli, Gustavo Pablo; Sathicq, Ángel Gabriel; Martínez Zambrano, José Jobanny; Afonso, Carlos A. M.
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The acid-promoted methanolysis of oleuropein was studied using a variety of homogeneous and heterogeneous acid catalysts. Exclusive cleavage of the acetal bond between the glucoside and the monoterpene subunits or further hydrolysis of the hydroxytyrosol ester and subsequent intramolecular rearrangement were observed upon identification of the most efficient catalyst and experimental conditions. Furthermore, selected conditions were tested using oleuropein under continuous flow and using a crude mixture extracted from olive leaves under batch. Formation of (−)-methyl elenolate was also observed in this study, which is a reported precursor for the synthesis of the antihypertensive drug (−)-ajmalicine.
Centro de Investigación y Desarrollo en Ciencias Aplicadas
Materia
Química
Ingeniería Química
Biomass
Homogeneous catalysis
Oleuropein
Solvolysis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/98234

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network_name_str SEDICI (UNLP)
spelling Valorization of Oleuropein via Tunable Acid-Promoted MethanolysisCavaca, Lídia A. S.Rodrigues, Catarina A. B.Simeonov, Svilen P.Gomes, Rafael F. A.Coelho, Jaime A. S.Romanelli, Gustavo PabloSathicq, Ángel GabrielMartínez Zambrano, José JobannyAfonso, Carlos A. M.QuímicaIngeniería QuímicaBiomassHomogeneous catalysisOleuropeinSolvolysisThe acid-promoted methanolysis of oleuropein was studied using a variety of homogeneous and heterogeneous acid catalysts. Exclusive cleavage of the acetal bond between the glucoside and the monoterpene subunits or further hydrolysis of the hydroxytyrosol ester and subsequent intramolecular rearrangement were observed upon identification of the most efficient catalyst and experimental conditions. Furthermore, selected conditions were tested using oleuropein under continuous flow and using a crude mixture extracted from olive leaves under batch. Formation of (−)-methyl elenolate was also observed in this study, which is a reported precursor for the synthesis of the antihypertensive drug (−)-ajmalicine.Centro de Investigación y Desarrollo en Ciencias Aplicadas2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf2300-2305http://sedici.unlp.edu.ar/handle/10915/98234enginfo:eu-repo/semantics/altIdentifier/url/https://ri.conicet.gov.ar/11336/86018info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cssc.201800980info:eu-repo/semantics/altIdentifier/issn/1864-5631info:eu-repo/semantics/altIdentifier/doi/10.1002/cssc.201800980info:eu-repo/semantics/altIdentifier/hdl/11336/86018info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/2.5/ar/Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Argentina (CC BY-NC-SA 2.5)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:20:30Zoai:sedici.unlp.edu.ar:10915/98234Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:20:31.251SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
title Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
spellingShingle Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
Cavaca, Lídia A. S.
Química
Ingeniería Química
Biomass
Homogeneous catalysis
Oleuropein
Solvolysis
title_short Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
title_full Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
title_fullStr Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
title_full_unstemmed Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
title_sort Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis
dc.creator.none.fl_str_mv Cavaca, Lídia A. S.
Rodrigues, Catarina A. B.
Simeonov, Svilen P.
Gomes, Rafael F. A.
Coelho, Jaime A. S.
Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Martínez Zambrano, José Jobanny
Afonso, Carlos A. M.
author Cavaca, Lídia A. S.
author_facet Cavaca, Lídia A. S.
Rodrigues, Catarina A. B.
Simeonov, Svilen P.
Gomes, Rafael F. A.
Coelho, Jaime A. S.
Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Martínez Zambrano, José Jobanny
Afonso, Carlos A. M.
author_role author
author2 Rodrigues, Catarina A. B.
Simeonov, Svilen P.
Gomes, Rafael F. A.
Coelho, Jaime A. S.
Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Martínez Zambrano, José Jobanny
Afonso, Carlos A. M.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
Ingeniería Química
Biomass
Homogeneous catalysis
Oleuropein
Solvolysis
topic Química
Ingeniería Química
Biomass
Homogeneous catalysis
Oleuropein
Solvolysis
dc.description.none.fl_txt_mv The acid-promoted methanolysis of oleuropein was studied using a variety of homogeneous and heterogeneous acid catalysts. Exclusive cleavage of the acetal bond between the glucoside and the monoterpene subunits or further hydrolysis of the hydroxytyrosol ester and subsequent intramolecular rearrangement were observed upon identification of the most efficient catalyst and experimental conditions. Furthermore, selected conditions were tested using oleuropein under continuous flow and using a crude mixture extracted from olive leaves under batch. Formation of (−)-methyl elenolate was also observed in this study, which is a reported precursor for the synthesis of the antihypertensive drug (−)-ajmalicine.
Centro de Investigación y Desarrollo en Ciencias Aplicadas
description The acid-promoted methanolysis of oleuropein was studied using a variety of homogeneous and heterogeneous acid catalysts. Exclusive cleavage of the acetal bond between the glucoside and the monoterpene subunits or further hydrolysis of the hydroxytyrosol ester and subsequent intramolecular rearrangement were observed upon identification of the most efficient catalyst and experimental conditions. Furthermore, selected conditions were tested using oleuropein under continuous flow and using a crude mixture extracted from olive leaves under batch. Formation of (−)-methyl elenolate was also observed in this study, which is a reported precursor for the synthesis of the antihypertensive drug (−)-ajmalicine.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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://sedici.unlp.edu.ar/handle/10915/98234
url http://sedici.unlp.edu.ar/handle/10915/98234
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://ri.conicet.gov.ar/11336/86018
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cssc.201800980
info:eu-repo/semantics/altIdentifier/issn/1864-5631
info:eu-repo/semantics/altIdentifier/doi/10.1002/cssc.201800980
info:eu-repo/semantics/altIdentifier/hdl/11336/86018
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Argentina (CC BY-NC-SA 2.5)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Argentina (CC BY-NC-SA 2.5)
dc.format.none.fl_str_mv application/pdf
2300-2305
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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