Abstract
This research deals with the determination of solubility, Hansen solubility parameters, dissolution properties, enthalpy–entropy compensation, and computational modeling of a naturally-derived bioactive compound trans-resveratrol (TRV) in water, methanol, ethanol, n-propanol, n-butanol, propylene glycol (PG), and various PG + water mixtures. The solubility of TRV in six different mono-solvents and various PG + water mixtures was determined at 298.2–318.2 K and 0.1 MPa. The measured experimental solubility values of TRV were regressed using six different computational/theoretical models, including van’t Hoff, Apelblat, Buchowski–Ksiazczak λh, Yalkowsly–Roseman, Jouyban–Acree, and van’t Hoff–Jouyban–Acree models, with average uncertainties of less than 3.0%. The maxima of TRV solubility in mole fraction was obtained in neat PG (2.62 × 10−2) at 318.2 K. However, the minima of TRV solubility in the mole fraction was recorded in neat water (3.12 × 10−6) at 298.2 K. Thermodynamic calculation of TRV dissolution properties suggested an endothermic and entropy-driven dissolution of TRV in all studied mono-solvents and various PG + water mixtures. Solvation behavior evaluation indicated an enthalpy-driven mechanism as the main mechanism for TRV solvation. Based on these data and observations, PG has been chosen as the best mono-solvent for TRV solubilization.
Highlights
Published: 21 May 2021Trans-resveratrol (TRV) {molecular structure: Figure 1; IUPAC name: 5-[(E)-2-(4hydroxyphenyl) ethenyl] benzene-1,3-diol; molecular formula: C14 H12 O3 ; molar mass: 228.24 g mol−1 ; PubChem CID: 445154, and CAS: 501-36-0]} is a naturally-derived white crystalline powder [1,2]
Its therapeutic effects are limited after oral administration because of its poor solubility in water, instability in physiological fluids, short plasma half-life, and extensive first-pass metabolism, despite its high permeability [12,13]
The experimental solubility of TRV in water was observed in good agreement with those reported in the literature [1,27]
Summary
Trans-resveratrol (TRV) {molecular structure: Figure 1; IUPAC name: 5-[(E)-2-(4hydroxyphenyl) ethenyl] benzene-1,3-diol; molecular formula: C14 H12 O3 ; molar mass: 228.24 g mol−1 ; PubChem CID: 445154, and CAS: 501-36-0]} is a naturally-derived white crystalline powder [1,2]. It is isolated from various plant sources, such as peanuts, grapes, and berries [2,3]. TRV has shown multiple intracellular targeting properties [4]. Because of its multiple intracellular targeting properties, it has shown different therapeutic activities, such as antioxidant, cardiovascular, anti-inflammatory, neuroprotective, antidiabetic, and anticarcinogenic properties [5,6,7,8,9,10,11]. Various formulation strategies, such as cyclodextrin complexation [14], polymeric microparticles [15], polymeric nanoparticles [16,17], nanosponges [18], nanostructured lipid carriers [19], polymeric micelles [20], self-emulsifying drug delivery systems [21,22], self-microemulsifying drug delivery systems [23], and nanosuspensions [24] have been
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