Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation

abstract

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.

keywords

COSMO-RS

subject category

Biochemistry & Molecular Biology; Chemistry

authors

Teixeira, G; Abranches, DO; Silva, LP; Vilas-Boas, SM; Pinho, SP; Ferreira, AIMCL; Santos, LMNBF; Ferreira, O; Coutinho, JAP

Groups

G4 - Renewable Materials and Circular Economy
G6 - Virtual Materials and Artificial Intelligence

Projects

CICECO - Aveiro Institute of Materials (UIDB/50011/2020)

CICECO - Aveiro Institute of Materials (UIDP/50011/2020)

Associated Laboratory CICECO-Aveiro Institute of Materials (LA/P/0006/2020)

acknowledgements

This research was developed within the scope of the project CICECO-Aveiro Institute of Materials, UIDB/50011/2020, UIDP/50011/2020, and LA/P/0006/2020, and project CIMO-Mountain Research Center, UIDB/00690/2020 and LA/P/0007/2020, financed by national funds through the Portuguese Foundation for Science and Technology/MCTES. Support was also provided by project Al lNat-POCI-01-0145-FEDER-030463 (PTDC/EQU-EPQ/30463/2017), funded by FEDER funds through COMPETE2020-Prog. Operacional Competitividade e InternacionalizacAo (POCI), and by national funds through the Foundation for Science and Technology (FCT/MCTES). This work was supported by the FundacAo para a Ciencia e Tecnologia (FCT) (funded by national funds through the FCT/MCTES (PIDDAC)) to CIQUP, Faculty of Science, University of Porto (Project UIDB/00081/2020), IMS-Institute of Molecular Sciences (LA/P/0056/2020)). A.I.M.C.L.F. is financed by national funds through the FCT-I.P., in the framework of the execution of the program contract provided in paragraphs 4, 5, and 6 of art. 23 of Law no. 57/2016 of 29 August, as amended by Law no. 57/2017 of 19 July. G.T. and S.M.V.B. acknowledge FCT/MCTES for the Ph.D. grants UI/BD/151114/2021 and SFRH/BD/138149/ 2018, respectively.