Solubility and Solution Thermodynamic Properties of 4-(4-Hydroxyphenyl)-2-butanone (Raspberry Ketone) in Different Pure Solvents

Shu, Min; Zhu, Liang; Yuan, Min; Wang, Li-Yu; Wang, Yanfei; Yang, Libin; Zhou, Sha; Zeng, Meng

doi:10.1007/s10953-017-0681-0

Cited by 9 publications

(5 citation statements)

References 27 publications

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“…In this work, the positive Δ mix H of the mixing process showed that the interactions between solute molecules were stronger than the interactions between QPE and solvent molecules; thus, the system needs to absorb extra energy from the environment during dissolution. ,− Δ mix S shows the change of randomness of the system during the mixing process. The Δ mix S in the studied systems are all positive, indicating that the mixing process of QPE is entropy-driven − and is consistent with the principle of entropy increase.…”

Section: Resultssupporting

confidence: 75%

Determination and Correlation of Solubility of Quizalofop-p-ethyl in Seven Pure Solvents and Three Binary Solvents

Bai

Yang

et al. 2021

J. Chem. Eng. Data

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The solubility of quizalofop-p-ethyl (QPE) in seven pure solvents and three binary solvents (n-heptane + ethanol/ethyl acetate/acetone) in the temperature range from 278.15 to 318.15 K was determined by using the gravimetric method. It is found that the solubility of QPE in the seven pure solvents from 278.15 to 303.15 K follows the order: acetone > ethyl acetate > isobutyl alcohol > tert-butanol > ethanol > n-heptane > n-hexane. In each pure solvent, the QPE solubility increases with increasing temperature. In the three binary solvent systems, the QPE solubility increases with increasing temperature and increasing proportion of good solvent, i.e., ethanol/ethyl acetate/acetone. The experimental solubility of QPE in pure solvents was correlated by the modified Apelblat equation, λh model, and NRTL model, among which modified the Apelblat model gave the best accuracy with RMSD and ARD of less than 0.8100 × 10–4 and 10.26%, respectively. The solubility in the binary solvent systems was correlated by the λh model, NRTL model, and CNIBS/R-K equation, which also provided good correlation accuracy with RMSD and ARD less than 1.258 × 10–3 and 6.61%, respectively. Furthermore, the thermodynamic properties including the mixed thermodynamic properties of Gibbs energy change (Δmix G), molar enthalpy change (Δmix H), and molar entropy change (Δmix S) were calculated from the experimental solubility data by using the NRTL model. The negative Δmix G and positive Δmix H and Δmix S indicate that the mixed processes of QPE in the test solvent systems are all endothermic and entropically favorable. The experimental solubility and the models used in this work would be conducive to purifying QPE via crystallization.

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Section: Resultssupporting

confidence: 75%

Determination and Correlation of Solubility of Quizalofop-p-ethyl in Seven Pure Solvents and Three Binary Solvents

Bai

Yang

et al. 2021

J. Chem. Eng. Data

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“…The temperature dependence of the drug solubility in a solvent can be modeled by empirical correlation [ 17 , 18 ], and by the activity coefficient method [ 19 , 20 ]. To select an appropriate model to describe the solubility of metoprolol succinate in the tested solvents, the experimental solubility data were correlated using three models: the modified Apelblat equation [ 21 ], the Wilson model [ 22 ], and the NRTL model [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…The modified Apelblat equation that is derived from the Clausius-Clapeyron model is shown in Equation (4) [ 18 ]:

…”

Section: Resultsmentioning

confidence: 99%

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Shen

Liang

2018

Molecules

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The solubilities of metoprolol succinate (a cardioselective β1 adrenergic receptor) in methanol, ethanol, n-propanol, isopropanol, n-butanol, ethyl acetate, and acetone were measured at temperatures ranging from (278.2 to 318.2) K using a solid–liquid equilibrium method. The solubility of metoprolol succinate increases with increasing temperature. At a fixed temperature, the solubility decreases in the order methanol > ethanol > n-butanol > n-propanol > isopropanol > acetone > ethyl acetate. The enthalpy of fusion and the melting point of metoprolol succinate were determined by differential scanning calorimetry. The thermodynamic properties of the dissolution process, determined by a van’t Hoff analysis, have been obtained and are discussed. The modified Apelblat equation, Wilson model, and non-random two-liquid (NRTL) model were employed to correlate the solubilities of metoprolol succinate in different solvents. Finally, a quantitative structure–property relationship (QSPR) study of physical properties of solvents and density functional theory simulations of hydrogen-bonding structure were carried out to give the explanation for the sequence of solubility in alcohols. The density functional theory (DFT) calculations well illustrated that the solubility of metoprolol succinate in various alcohols can be mainly attributed to the intra- and intermolecular hydrogen bonds in metoprolol succinate-solvent complexes.

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“…As is the case with other properties, reliable experimental values for the aqueous solubility for RK are scarce. One study employing gravimetric measurements reports the solubility as 0.05 M at 298 K, while chemometric predictions range from 0.001 to 0.014 M (0.16–2.30 mg·mL –1 ) which would place RK within the very slightly soluble to slightly soluble range of the European Pharmacopeia. We evaluated solubility using a general solubility equation based on that originally developed by Ran and Yalkowsky .…”

Section: Resultsmentioning

confidence: 99%

Physicochemical Properties of 4-(4-Hydroxyphenyl)-butan-2-one (“Raspberry Ketone”) Evaluated Using a Computational Chemistry Approach

McPherson,

McKenna,

Johnston

2024

ACS Omega

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Raspberry ketone (RK) is a product of the phenylpropanoid pathway in a variety of plants and is the second most expensive natural flavouring in the world. It is also widely used as a nutritional supplement due to its reported ability to promote lipolysis and fat oxidation in vivo. We have evaluated the thermodynamics of RK using the correlation consistent ccCA-CBS-2 approach which afforded calculation of (inter alia) the enthalpy of formation. To obtain pK a, log D, electrode potential, solubility, and reactivity indices, we used TPSS/def2-TZVP geometries followed by single-point energies obtained at the M06-2X/def2-TZVPP level of theory. We obtained Δf H = −299.4 ± 0.17 kJ·mol–1; the pK a and logD were found to be 9.95 and 1.84, respectively, consistent with chemometric predictions. Using the enthalpy of fusion obtained from theory, we evaluated the aqueous solubility of RK to be in the region of 2.5 mg·mL–1 which is in agreement with limited literature reports. In terms of reactivity, we obtained a formal electrode potential of 1.29 V (vs SHE) at pH 7.4 and 298.15 K. The HOMO–LUMO energy separation in an aqueous environment was found to be ca. 7.8 eV, suggesting moderate chemical reactivity. Analysis of the frontier molecular orbitals using conceptual density functional theory supported this and revealed a reactivity pattern consistent with the metabolite profile obtained in mammals, namely, a propensity for nucleophilic attack at the carbonyl carbon and electrophilic addition of the benzene ring.

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Solubility and Solution Thermodynamic Properties of 4-(4-Hydroxyphenyl)-2-butanone (Raspberry Ketone) in Different Pure Solvents

Cited by 9 publications

References 27 publications

Determination and Correlation of Solubility of Quizalofop-p-ethyl in Seven Pure Solvents and Three Binary Solvents

Determination and Correlation of Solubility of Quizalofop-p-ethyl in Seven Pure Solvents and Three Binary Solvents

Measurements, Thermodynamic Modeling, and a Hydrogen Bonding Study on the Solubilities of Metoprolol Succinate in Organic Solvents

Physicochemical Properties of 4-(4-Hydroxyphenyl)-butan-2-one (“Raspberry Ketone”) Evaluated Using a Computational Chemistry Approach

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