Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers

Hydroxycinnamic acids, such as coumaric, ferulic, and caffeic acids, stand out for their pharmacological and cosmetic applications due to their bioactive properties. However, their low solubility in water and conventional solvents can be considered a drawback for their effective utilization. This st...

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Autores: Gracia-Barberán, Sara, Lanau, María, Leal-Duaso, Alejandro, López-Ram-de-Víu, Pilar, Mainar, Ana M., Mayoral, José A., Pires, Elísabet
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/400727
Acceso en línea:http://hdl.handle.net/10261/400727
Access Level:acceso abierto
Palabra clave:Green solvents
Solubility
Glycerol ethers
Hydroxycinnamic acid
Ferulic
Coumaric
Caffeic
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spelling Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethersGracia-Barberán, SaraLanau, MaríaLeal-Duaso, AlejandroLópez-Ram-de-Víu, PilarMainar, Ana M.Mayoral, José A.Pires, ElísabetGreen solventsSolubilityGlycerol ethersHydroxycinnamic acidFerulicCoumaricCaffeicHydroxycinnamic acids, such as coumaric, ferulic, and caffeic acids, stand out for their pharmacological and cosmetic applications due to their bioactive properties. However, their low solubility in water and conventional solvents can be considered a drawback for their effective utilization. This study investigates the solubility of these acids in renewable glycerol-derived ethers, which exhibit good ecotoxicological profiles and tunable physicochemical properties. Experimental solubility data revealed that monoethers and diethers with shorter alkyl chains significantly enhance the solubility of the studied hydroxycinnamic acids. The findings were further corroborated by COSMO-RS modeling, highlighting the importance of both hydrogen-bond donor capacity and polarity-polarizability in solubility enhancement. Hydrotropic effects of glycerol ethers in water were also experimentally demonstrated, indicating their potential in pharmaceutical and industrial formulations. These results underscore the efficacy of glycerol-derived solvents as sustainable alternatives for solubilizing hydroxycinnamic acids, paving the way for greener and more efficient applications.This work was financially supported by the Spanish Agency of Research (AEI) (project number PID2021-125762NB-I00), the Gobierno de Aragón (E37_23R and E39-23R groups), and the European Union NextGenerationEU funds through the “Programa Margarita Salas 2021–2023”.S.G.-B. acknowledges the Cátedra SAMCA de Desarrollo Tecnológico de Aragón for her contract. A.L.-D. acknowledges the “Programa Margarita Salas 2021–2023” (Plan Nacional de Recuperación, Transformación y Resiliencia), financed by the European Union-NextGenerationEU through the Ministerio de Universidades of Spain and the University of Zaragoza.Peer reviewedAmerican Chemical SocietyAgencia Estatal de Investigación (España)Ministerio de Ciencia, Innovación y Universidades (España)Gobierno de AragónEuropean CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202520252025info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/400727reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-125762NB-I00Gracia-Barberán, Sara; Lanau, María; Leal-Duaso, Alejandro; López-Ram-de-Víu, Pilar; Mainar, Ana M.; Mayoral, José A.; Pires, Elísabet; 2025; Supporting Information: Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers [Dataset]; American Chemical Society; https://doi.org/10.1021/acssuschemeng.5c00269https://doi.org/10.1021/acssuschemeng.5c00269Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/4007272026-05-22T06:33:51Z
dc.title.none.fl_str_mv Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
title Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
spellingShingle Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
Gracia-Barberán, Sara
Green solvents
Solubility
Glycerol ethers
Hydroxycinnamic acid
Ferulic
Coumaric
Caffeic
title_short Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
title_full Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
title_fullStr Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
title_full_unstemmed Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
title_sort Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers
dc.creator.none.fl_str_mv Gracia-Barberán, Sara
Lanau, María
Leal-Duaso, Alejandro
López-Ram-de-Víu, Pilar
Mainar, Ana M.
Mayoral, José A.
Pires, Elísabet
author Gracia-Barberán, Sara
author_facet Gracia-Barberán, Sara
Lanau, María
Leal-Duaso, Alejandro
López-Ram-de-Víu, Pilar
Mainar, Ana M.
Mayoral, José A.
Pires, Elísabet
author_role author
author2 Lanau, María
Leal-Duaso, Alejandro
López-Ram-de-Víu, Pilar
Mainar, Ana M.
Mayoral, José A.
Pires, Elísabet
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Gobierno de Aragón
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Green solvents
Solubility
Glycerol ethers
Hydroxycinnamic acid
Ferulic
Coumaric
Caffeic
topic Green solvents
Solubility
Glycerol ethers
Hydroxycinnamic acid
Ferulic
Coumaric
Caffeic
description Hydroxycinnamic acids, such as coumaric, ferulic, and caffeic acids, stand out for their pharmacological and cosmetic applications due to their bioactive properties. However, their low solubility in water and conventional solvents can be considered a drawback for their effective utilization. This study investigates the solubility of these acids in renewable glycerol-derived ethers, which exhibit good ecotoxicological profiles and tunable physicochemical properties. Experimental solubility data revealed that monoethers and diethers with shorter alkyl chains significantly enhance the solubility of the studied hydroxycinnamic acids. The findings were further corroborated by COSMO-RS modeling, highlighting the importance of both hydrogen-bond donor capacity and polarity-polarizability in solubility enhancement. Hydrotropic effects of glycerol ethers in water were also experimentally demonstrated, indicating their potential in pharmaceutical and industrial formulations. These results underscore the efficacy of glycerol-derived solvents as sustainable alternatives for solubilizing hydroxycinnamic acids, paving the way for greener and more efficient applications.
publishDate 2025
dc.date.none.fl_str_mv 2025
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/400727
url http://hdl.handle.net/10261/400727
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-125762NB-I00
Gracia-Barberán, Sara; Lanau, María; Leal-Duaso, Alejandro; López-Ram-de-Víu, Pilar; Mainar, Ana M.; Mayoral, José A.; Pires, Elísabet; 2025; Supporting Information: Eco-friendly solvents for bioactives: Solubilization of hydroxycinnamic acids in glycerol-derived ethers [Dataset]; American Chemical Society; https://doi.org/10.1021/acssuschemeng.5c00269
https://doi.org/10.1021/acssuschemeng.5c00269
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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