Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures

Abdelkarim Aydi; Cherifa Ayadi; Kaouther Ghachem; Abdulaal Z Al-Khazaal; Daniel R Delgado; Mohammad Alnaief; Lioua Kolsi

doi:10.3390/ph13110395

Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures

Pharmaceuticals (Basel). 2020 Nov 16;13(11):395. doi: 10.3390/ph13110395.

Authors

Abdelkarim Aydi^{1

2}, Cherifa Ayadi^{3

4}, Kaouther Ghachem⁵, Abdulaal Z Al-Khazaal⁶, Daniel R Delgado⁷, Mohammad Alnaief⁸, Lioua Kolsi^{9

10}

Affiliations

¹ LETIAM, Lip (Sys)2, IUT d'Orsay, Université Paris-Sud, Plateau de Moulon, 91400 Orsay, France.
² Laboratory of Materials Molecules and Applications, Preparatory Institute for Scientific and Technical Studies, University of Carthage, Tunis 1082, Tunisia.
³ Laboratory of Materials, Treatment and Analysis (LMTA), National Institute of Research and Physicochemical Analysis (INRAP), BiotechPole Sidi-Thabet, Ariana 2020, Tunisia.
⁴ Faculté des Sciences de Tunis, Université Tunis El Manar, Campus Universitaire El Manar, Tunis 2092, Tunisia.
⁵ Department of Industrial Engineering and Systems, College of Engineering, Princess Nourah bint Abdulrahman University, Riyadh 84428, Saudi Arabia.
⁶ Department of Chemical and Materials Engineering, Faculty of Engineering, Northern Border University, Arar P.O. Box 1321, Saudi Arabia.
⁷ GRIAUCC Research Group, Department of Engineering, Industrial Engineering Program, Universidad Cooperativa de Colombia, Calle 11 No. 1-51, Neiva 410001, Huila, Colombia.
⁸ Department of Pharmaceutical and Chemical Engineering, Faculty of Applied Medical Sciences, German Jordanian University, Amman 11180, Jordan.
⁹ Department of Mechanical Engineering, College of Engineering, Ha'il University, Ha'il City 81481, Saudi Arabia.
¹⁰ Laboratory of Metrology and Energy Systems, National Engineering School of Monastir, University of Monastir, Monastir 5000, Tunisia.

Abstract

The equilibrium solubility of amygdalin in [ethanol (1) + water (2)] mixtures at 293.15 K to 328.15 K was reported. The thermodynamic properties (standard enthalpy Δ_solnH°, standard entropy Δ_solnS°, and standard Gibbs energy of solution Δ_solnG°) were computed using the generated solubility data via van't Hoff and Gibbs equations. The dissolution process of amygdalin is endothermic and the driving mechanism in all mixtures is entropy. Maximal solubility was achieved in 0.4 mole fraction of ethanol at 328.15 K and the minimal one in neat ethanol at 293.15 K. Van't Hoff, Jouyban-Acree-van't Hoff, and Buchowski-Ksiazczak models were used to simulate the obtained solubility data. The calculated solubilities deviate reasonably from experimental data. Preferential solvation parameters of amygdalin in mixture solvents were analyzed using the inverse Kirkwood-Buff integrals (IKBI) method. Amygdalin is preferentially solvated by water in ethanol-rich mixtures, whereas in water-rich mixtures, there is no clear evidence that determines which of water or ethanol solvents would be most likely to solvate the molecule.

Keywords: Buchowski–Ksiazczak; Gibbs equation; Jouyban–Acree; amygdalin; inverse Kirkwood–Buff integral; solubility; thermodynamics; van’t Hoff.