Eco-Friendly Solvents for Bioactives: Solubilization of Hydroxycinnamic Acids in Glycerol-Derived Ethers

Gracia-Barberán, Sara ; Lanau, María ; Leal-Duaso, Alejandro ; López Ram de Viu, Pilar (Universidad de Zaragoza) ; Mainar, Ana M. (Universidad de Zaragoza) ; Mayoral, José A. (Universidad de Zaragoza) ; Pires, Elísabet (Universidad de Zaragoza)

Resumen: 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.

Idioma: Inglés

DOI: 10.1021/acssuschemeng.5c00269

Año: 2025

Publicado en: ACS Sustainable Chemistry and Engineering (2025), [11 pp.]
ISSN: 2168-0485

Financiación: info:eu-repo/grantAgreement/ES/DGA/E37-23R
Financiación: info:eu-repo/grantAgreement/ES/DGA/E39-23R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/PID2021-125762NB-I00

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
Área (Departamento): Área Química Física (Dpto. Química Física)