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, Angel Gabriel; Martínez, José J.; 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.
Fil: Cavaca, Lídia A. S.. Universidade de Lisboa; Portugal
Fil: Rodrigues, Catarina A. B.. Universidade de Lisboa; Portugal
Fil: Simeonov, Svilen P.. Universidade de Lisboa; Portugal. Bulgarian Academy of Science; Bulgaria
Fil: Gomes, Rafael F. A.. Universidade de Lisboa; Portugal
Fil: Coelho, Jaime A. S.. Universidade de Lisboa; Portugal
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Afonso, Carlos A. M.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Materia
BIOMASS
HETEROGENEOUS CATALYSIS
HOMOGENEOUS CATALYSIS
OLEUROPEIN
SOLVOLYSIS
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:11336/86018
Acceder
id CONICETDig_f968b547300da6d86079fc1769437b6e
oai_identifier_str oai:ri.conicet.gov.ar:11336/86018
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
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, Angel GabrielMartínez, José J.Afonso, Carlos A. M.BIOMASSHETEROGENEOUS CATALYSISHOMOGENEOUS CATALYSISOLEUROPEINSOLVOLYSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The 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.Fil: Cavaca, Lídia A. S.. Universidade de Lisboa; PortugalFil: Rodrigues, Catarina A. B.. Universidade de Lisboa; PortugalFil: Simeonov, Svilen P.. Universidade de Lisboa; Portugal. Bulgarian Academy of Science; BulgariaFil: Gomes, Rafael F. A.. Universidade de Lisboa; PortugalFil: Coelho, Jaime A. S.. Universidade de Lisboa; PortugalFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Afonso, Carlos A. M.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaWiley VCH Verlag2018-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/86018Cavaca, Lídia A. S.; Rodrigues, Catarina A. B.; Simeonov, Svilen P.; Gomes, Rafael F. A.; Coelho, Jaime A. S.; et al.; Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis; Wiley VCH Verlag; Chemsuschem; 11; 14; 7-2018; 2300-23051864-5631CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/cssc.201800980info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cssc.201800980info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:17:57Zoai:ri.conicet.gov.ar:11336/86018instacron: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:34982025-09-29 10:17:57.391CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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.
BIOMASS
HETEROGENEOUS CATALYSIS
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, Angel Gabriel
Martínez, José J.
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, Angel Gabriel
Martínez, José J.
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, Angel Gabriel
Martínez, José J.
Afonso, Carlos A. M.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv BIOMASS
HETEROGENEOUS CATALYSIS
HOMOGENEOUS CATALYSIS
OLEUROPEIN
SOLVOLYSIS
topic BIOMASS
HETEROGENEOUS CATALYSIS
HOMOGENEOUS CATALYSIS
OLEUROPEIN
SOLVOLYSIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
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.
Fil: Cavaca, Lídia A. S.. Universidade de Lisboa; Portugal
Fil: Rodrigues, Catarina A. B.. Universidade de Lisboa; Portugal
Fil: Simeonov, Svilen P.. Universidade de Lisboa; Portugal. Bulgarian Academy of Science; Bulgaria
Fil: Gomes, Rafael F. A.. Universidade de Lisboa; Portugal
Fil: Coelho, Jaime A. S.. Universidade de Lisboa; Portugal
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Afonso, Carlos A. M.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
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 2018-07
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/11336/86018
Cavaca, Lídia A. S.; Rodrigues, Catarina A. B.; Simeonov, Svilen P.; Gomes, Rafael F. A.; Coelho, Jaime A. S.; et al.; Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis; Wiley VCH Verlag; Chemsuschem; 11; 14; 7-2018; 2300-2305
1864-5631
CONICET Digital
CONICET
url http://hdl.handle.net/11336/86018
identifier_str_mv Cavaca, Lídia A. S.; Rodrigues, Catarina A. B.; Simeonov, Svilen P.; Gomes, Rafael F. A.; Coelho, Jaime A. S.; et al.; Valorization of Oleuropein via Tunable Acid-Promoted Methanolysis; Wiley VCH Verlag; Chemsuschem; 11; 14; 7-2018; 2300-2305
1864-5631
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/cssc.201800980
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cssc.201800980
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
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1844614137135497216
score 13.070432

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