Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation
Gabriel Teixeira,
Dinis O. Abranches,
Liliana P. Silva,
Sérgio M. Vilas-Boas,
Simão P. Pinho,
Ana I. M. C. L. Ferreira,
Luís M. N. B. F. Santos,
Olga Ferreira,
João A. P. Coutinho
Affiliations
Gabriel Teixeira
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Dinis O. Abranches
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Liliana P. Silva
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Sérgio M. Vilas-Boas
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Simão P. Pinho
Mountain Research Center (CIMO), Polytechnic Institute of Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
Ana I. M. C. L. Ferreira
CIQUP, Institute of Molecular Sciences (IMS)—Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua Campo Alegre, 4169-007 Porto, Portugal
Luís M. N. B. F. Santos
CIQUP, Institute of Molecular Sciences (IMS)—Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua Campo Alegre, 4169-007 Porto, Portugal
Olga Ferreira
Mountain Research Center (CIMO), Polytechnic Institute of Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
João A. P. Coutinho
CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
The formation of deep eutectic solvents (DES) is tied to negative deviations to ideality caused by the establishment of stronger interactions in the mixture than in the pure DES precursors. This work tested thymol and menthol as hydrogen bond donors when combined with different flavonoids. Negative deviations from ideality were observed upon mixing thymol with either flavone or flavanone, two parent flavonoids that only have hydrogen bond acceptor (HBA) groups, thus forming non-ionic DES (Type V). On the other hand, the menthol systems with the same compounds generally showed positive deviations from ideality. That was also the case with the mixtures containing the more complex hydroxylated flavonoid, hesperetin, which resulted in positive deviations when mixed with either thymol or menthol. COSMO-RS successfully predicted the behavior of the solid-liquid phase diagram of the studied systems, allowing for evaluation of the impact of the different contributions to the intermolecular interactions, and proving to be a good tool for the design of DES.
