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Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation.

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This study explores deep eutectic solvents (DES) formation using thymol or menthol with flavonoids. Thymol formed non-ionic DES with flavone/flavanone, indicating stronger interactions, while menthol mixtures showed different behavior.

Keywords:
COSMO-RSdeep eutectic solventsflavonoidssolid-liquid equilibriaterpenoids

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Deep eutectic solvents (DES) form due to stronger interactions in mixtures than in pure precursors, leading to negative deviations from ideality.
  • Hydrogen bond donors like thymol and menthol interact with hydrogen bond acceptor groups on flavonoids.

Purpose of the Study:

  • To investigate the formation of DES by combining thymol and menthol with various flavonoids.
  • To analyze the deviations from ideality and understand the intermolecular interactions governing DES formation.
  • To evaluate the predictive capability of COSMO-RS for designing DES.

Main Methods:

  • Mixing thymol and menthol with parent flavonoids (flavone, flavanone) and a hydroxylated flavonoid (hesperetin).
  • Observing deviations from ideality in the resulting mixtures.
  • Utilizing COSMO-RS simulations to predict phase diagram behavior and analyze intermolecular forces.

Main Results:

  • Thymol formed non-ionic DES (Type V) with flavone and flavanone, showing negative deviations from ideality.
  • Menthol systems and thymol/menthol mixtures with hesperetin generally exhibited positive deviations from ideality.
  • COSMO-RS accurately predicted solid-liquid phase diagram behavior for the studied systems.

Conclusions:

  • The choice of hydrogen bond donor and acceptor significantly influences DES formation and ideality deviations.
  • COSMO-RS is a valuable tool for predicting DES behavior and guiding the design of new solvent systems.
  • Understanding intermolecular interactions is crucial for the rational design of novel deep eutectic solvents.