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Solubility measurement and molecular simulation of unsolvated and solvated estrogen receptor agonist (R)-equol in binary solvents (alcohols + n-heptane) from 273.15 K to 333.15 K.

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Title: Solubility measurement and molecular simulation of unsolvated and solvated estrogen receptor agonist (R)-equol in binary solvents (alcohols + n-heptane) from 273.15 K to 333.15 K.
Authors: Lou, Boxuan1 (AUTHOR), Xu, Yue1 (AUTHOR) 394073276@qq.com, Qin, Xiaolan1 (AUTHOR), Liu, Chang1 (AUTHOR), Wang, Shujun1 (AUTHOR), Yuan, Haikuan1 (AUTHOR), Liu, Xijian1 (AUTHOR), Zhang, Lijuan1 (AUTHOR), Lu, Jie1 (AUTHOR) lujie@sues.edu.cn
Source: Journal of Molecular Liquids. Apr2023, Vol. 376, pN.PAG-N.PAG. 1p.
Subjects: Heptane, Estrogen receptors, Solubility, Solvents, Hydrogen bonding interactions, Electric potential
Abstract: The solubility of unsolvated and solvated crystalline (R)-equol in alcohols and their mixtures with n -heptane were firstly systematically acquired from 273.15 K to 333.15 K. The transformation temperatures between unsolvated and solvated forms in methanol and ethanol were determined at 316.28 K and 310.50 K, respectively. The dissolution of unsolvated crystalline (R)-equol was found to be endothermic, to which the polarity of solvents, hydrogen bonding and van der Waals interactions should make main contributions. [Display omitted] • Solubilities of unsolvated crystalline (R)-equol in six binary mixed solvents were determined. • Transformation temperatures between unsolvated and solvated (R)-equol in methanol and ethanol were revealed. • Dissolution mechanism of (R)-equol in the studied solvents was identified by the aid of molecular simulations. In this work, the solubility of unsolvated crystalline (R)-equol in six (alcohols + n -heptane) binary solvents and that of solvated crystalline (R)-equol in methanol along with ethanol were firstly systematically measured and analyzed. The experimental results revealed that the solubility of unsolvated crystalline (R)-equol was positively correlated with temperature and mass fraction of alcohol. And the solubility order was 2-propanol > 1-propanol > 1-butanol > 1-pentanol > 3-methyl-1-butanol > 2-methyl-1-propanol > n -heptane. The transformation temperatures between unsolvated and solvated forms were acquired at 316.28 K and 310.50 K, respectively. Meanwhile, the experimental solubility data of unsolvated crystalline (R)-equol were correlated using modified Apelblat, λh , quartic polynomial and CNIBS/R-K equations, in which the modified Apelblat equation achieved the best regression performance. Besides, the dissolution of unsolvated crystalline (R)-equol was endothermic. Furthermore, solvent parameters, solvation free energy and molecular electrostatic potential surface obtained through molecular simulation were used to explain the experimental phenomena, and found the polarity of solvents, van der Waals and hydrogen bonding interactions made different contributions to various dissolution processes. [ABSTRACT FROM AUTHOR]
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Abstract:The solubility of unsolvated and solvated crystalline (R)-equol in alcohols and their mixtures with n -heptane were firstly systematically acquired from 273.15 K to 333.15 K. The transformation temperatures between unsolvated and solvated forms in methanol and ethanol were determined at 316.28 K and 310.50 K, respectively. The dissolution of unsolvated crystalline (R)-equol was found to be endothermic, to which the polarity of solvents, hydrogen bonding and van der Waals interactions should make main contributions. [Display omitted] • Solubilities of unsolvated crystalline (R)-equol in six binary mixed solvents were determined. • Transformation temperatures between unsolvated and solvated (R)-equol in methanol and ethanol were revealed. • Dissolution mechanism of (R)-equol in the studied solvents was identified by the aid of molecular simulations. In this work, the solubility of unsolvated crystalline (R)-equol in six (alcohols + n -heptane) binary solvents and that of solvated crystalline (R)-equol in methanol along with ethanol were firstly systematically measured and analyzed. The experimental results revealed that the solubility of unsolvated crystalline (R)-equol was positively correlated with temperature and mass fraction of alcohol. And the solubility order was 2-propanol > 1-propanol > 1-butanol > 1-pentanol > 3-methyl-1-butanol > 2-methyl-1-propanol > n -heptane. The transformation temperatures between unsolvated and solvated forms were acquired at 316.28 K and 310.50 K, respectively. Meanwhile, the experimental solubility data of unsolvated crystalline (R)-equol were correlated using modified Apelblat, λh , quartic polynomial and CNIBS/R-K equations, in which the modified Apelblat equation achieved the best regression performance. Besides, the dissolution of unsolvated crystalline (R)-equol was endothermic. Furthermore, solvent parameters, solvation free energy and molecular electrostatic potential surface obtained through molecular simulation were used to explain the experimental phenomena, and found the polarity of solvents, van der Waals and hydrogen bonding interactions made different contributions to various dissolution processes. [ABSTRACT FROM AUTHOR]
ISSN:01677322
DOI:10.1016/j.molliq.2023.121460