Effect of temperature and polarity on the solubility and preferential solvation of sinapic acid in aqueous mixtures of DMSO and Carbitol

Alshehri, Sultan; Shakeel, Faiyaz; Alam, Prawez; Peña, A.; Jouyban, Abolghasem; Martínez, Fleming

doi:10.1016/j.molliq.2021.117268

Cited by 23 publications

(14 citation statements)

References 32 publications

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“…However, the calculated Fedors δ 3 value of this compound is 29.0 MPa 1/2 as summarised in Table 1 [31], which is higher than δ 1 values of neat Transcutol® (22.3 MPa 1/2 ) and neat PEG 400 (24.0 MPa 1/2 ) [26]. Similar behaviour was reported earlier with sinapic acid and 6-phenyl-4,5-dihydropyridazin-3(2 H)-one dissolved in similar mixtures [23,24]. All these cases demonstrate that not only systems polarity but also other physicochemical properties of solutes and solvents play significant roles on the mixture compositions, exhibiting maximum drug solubilities.…”

Section: Effect Of Polarity On Tadalafil Solubilitysupporting

confidence: 82%

“…Thus, these complementary mathematical studies would provide deeper and specific thermodynamic data for molecular understanding of the dissolution processes of tadalafil in the reported cosolvent mixtures. Therefore, this research is similar to those about sinapic acid in aqueous mixtures of dimethyl sulphoxide (DMSO) and Carbitol® [23] and 6-phenyl-4,5-dihydropyridazin-3(2 H)-one in aqueous mixtures of Transcutol® and PEG 400, which were evaluated under similar conditions [24].…”

Section: Introductionmentioning

confidence: 78%

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Solubility of tadalafil in aqueous mixtures of Transcutol® and PEG 400 revisited: correlation, thermodynamics and preferential solvation

Shakeel

Alshehri

Ghoneim³

et al. 2022

Physics and Chemistry of Liquids

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Mole fraction solubilities of tadalafil (3) in aqueous mixtures of Transcutol® and PEG 400 at temperatures from 298.15 to 333.15 K were analysed following Hildebrand solubility parameters. Cosolvency models for representing tadalafil solubility at various temperatures were also provided for correlation/prediction purposes. Apparent thermodynamic quantities for tadalafil dissolution processes were calculated based on van't Hoff and Gibbs equations. Non-linear enthalpy-entropy compensation was observed for tadalafil transfer from more polar to less polar solvent systems. Preferential solvation parameters of tadalafil at 298.15 and 313.15 K were determined by means of the inverse Kirkwood-Buff integrals (IKBI). Tadalafil is preferentially solvated by water in water-rich mixtures of Transcutol® but preferentially solvated by Transcutol® in mixtures of 0.12 < x 1 < 1.00. In the former case, this result could be due to hydrophobic hydration around the non-polar moieties of tadalafil. Otherwise, tadalafil is preferentially solvated by PEG 400 in all the aqueous mixtures.

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Section: Effect Of Polarity On Tadalafil Solubilitysupporting

confidence: 82%

Section: Introductionmentioning

confidence: 78%

Solubility of tadalafil in aqueous mixtures of Transcutol® and PEG 400 revisited: correlation, thermodynamics and preferential solvation

Shakeel

Alshehri

Ghoneim³

et al. 2022

Physics and Chemistry of Liquids

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“…The δ x 1,3 of C 4 H 3 BrN 2 O (3) by organic solvents in methanol/ethanol/isopropanol/DMF (1) + water (2) is defined as − δ x 1 , 3 = x 1 , 3 normalL − x 1 = prefix− δ x 2 , 3 …”

Section: Resultsmentioning

confidence: 99%

“…If δ x 1,3 > 0, then the solute is preferentially solvated by organic solvents (1); on the contrary, if δ x 1,3 is <0, the solute is preferentially solvated by water (2). Values of δ x 1,3 can be obtained by the inverse Kirkwood–Buff integrals (IKBI) method that can be expressed as the following equations: − δ x 1 , 3 = x 1 x 2 ( G 1 , 3 − G 2 , 3 ) x 1 G 1 , 3 + x 2 G 2 , 3 + V cor with G 1 , 3 = R T κ normalT − V̅ 3 + x 2 V̅ 2 D Q G 2 , 3 = R T κ normalT − V̅ 3 + x 1 V̅ 1 D Q …”

Section: Resultsmentioning

confidence: 99%

Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

2023

J. Chem. Eng. Data

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The experimental solubility of 2-bromo-5-hydroxypyrazine dissolved in 10 mono-solvents (methanol, ethanol, isopropanol, N,N-dimethylformamide (DMF), npropanol, acetonitrile, acetone, ethylene glycol (EG), propylene glycol (PG), water) and cosolvent mixtures of methanol + water, ethanol + water, isopropanol + water, and DMF + water was determined by the isothermal saturation method between 278.15 and 323.15 K at 101.2 kPa. The largest solubility was observed in DMF + 2-bromo-5hydroxypyrazine for mono-solvent systems and in DMF + water for mixed solvent systems. The Jouyban−Acree model (J−A), van't Hoff−Jouyban−Acree model (V−J− A), and Apelblat−Jouyban−Acree model (A−J−A) were utilized to correlate the 2bromo-5-hydroxypyrazine solubility in mixtures, and the Apelblat model, van't Hoff model, λh model, and Jouyban model were used to correlate the 2-bromo-5hydroxypyrazine solubility in 10 mono-solvents. The preferential solvation of 2bromo-5-hydroxypyrazine in mixed solvents was researched by calculation of δx 1,3 . This study presents insights into modulating the 2-bromo-5-hydroxypyrazine crystallization process and in understanding equilibrium behaviors in different solvents.

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“…is not frequently reported in the literature. This is because of the big uncertainty obtained in its determination due to the low solubilities exhibited by them, particularly in aqueous media [38][39][40][41]. For this reason, in a first approach, the molar volume of allopurinol is considered here as independent of co-solvent composition, as it is calculated according to the groups contribution method proposed by Fedors [42] as 71.2 cm 3 •mol -1 .…”

Section: Preferential Solvationmentioning

confidence: 99%

Thermodynamic Analysis for the Solubility of Allopurinol in Aqueous and Non-aqueous Mixtures at Various Temperatures

et al. 2022

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The solubility of allopurinol was measured at several temperatures (15–35 ºC) in ethanol–water, ethanol–ethyl acetate, and ethyl acetate–hexane mixtures. The mole fraction solubility shows two solubility maxima against the co-solvent (ethanol) ratio (70 % ethanol–water and 100 % ethyl acetate) at each of the five temperatures studied. The authors correlated the solubility data in binary solvent mixtures at various temperatures using a modified version of the Jouyban–Acree model. The respective apparent thermodynamic functions Gibbs energy, enthalpy, and entropy of solution were obtained from the solubility data through the van’t Hoff equations. The apparent enthalpies of solution are endothermic and display a maximum at 20 % ethanol in water, as ethanol is added to water, the entropy of the system increases. In the non-aqueous mixture (ethanol–ethyl acetate), enthalpy is the driving force throughout the whole solvent composition. An enthalpy–entropy compensation analysis confirms a non-linear enthalpy–entropy relationship in plots of enthalpy vs. Gibbs energy of solution, i.e., two different mechanisms involved in the solubility enhancement. An inverse Kirkwood–Buff integral analysis of the preferential solvation indicated that in ethanol-rich mixtures, the drug is preferentially solvated by water, and it is acting mainly as a Lewis base in front to water.

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Effect of temperature and polarity on the solubility and preferential solvation of sinapic acid in aqueous mixtures of DMSO and Carbitol

Cited by 23 publications

References 32 publications

Solubility of tadalafil in aqueous mixtures of Transcutol® and PEG 400 revisited: correlation, thermodynamics and preferential solvation

Solubility of tadalafil in aqueous mixtures of Transcutol® and PEG 400 revisited: correlation, thermodynamics and preferential solvation

Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

Thermodynamic Analysis for the Solubility of Allopurinol in Aqueous and Non-aqueous Mixtures at Various Temperatures

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