Determination and modeling of the solubility of (limonin in methanol or acetone + water) binary solvent mixtures at T = 283.2 K to 318.2 K
Graphical abstract
Introduction
Limonin (C26H30O8, molar mass: 470.51 g mol−1, CAS number 1180-71-8, Fig. 1), a limonoid, is a kind of characteristic secondary metabolite belonging to highly oxygenated triterpenoid derivatives and enriched in citrus fruits [1], [2], [3], for example the fruit of Evodia rutaecarpa (Juss.) Benth, E. rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang, or E. rutaecarpa (Juss.) Benth. var. bodinieri (Dode) Huang or in seeds of lemon and orange. Limonin shows various biological activities and pharmacological properties [4], [5], [6], [7], [8], [9], including anticancer, antioxidant, anti-inflammatory, antifungal, analgesic and anti-HIV activities.
Limonin often coexists with rutaecarpine and evodiamine in Evodia fructus. To design an optimized separation process, it is essential to understand their solubilities in various solvents. The solubility of rutaecarpine and evodiamine in pure solvents and binary solvent mixtures had been reported in our previous works [10], [11], [12]. Chandler et al. reported the solubility of limonin only in water, and water at pH 6.3 and pH 3.2 [13]. Luo et al. reported the solubility of limonin only at 310.15 K in water, methanol, acetone and other solvents [14]. However, the solubility of Limonin in binary solvent mixtures has not been systematically studied. Therefore, in this work, the solubility of limonin in binary solvent mixtures (methanol + water) and (acetone + water) using various initial mole fractions was measured by high-performance liquid chromatography (HPLC) at different temperatures ranging from 283.2 K to 318.2 K. The measured solubility of limonin was then correlated by several models [15], [16], [17], including the van’t Hoff model, the modified Apelblat model, the CNIBS/Redlich–Kister model, simplified CNIBS/Redlich–Kister model, the Jouyban–Acree model, the van’t Hoff–Jouyban–Acree model, the modified Apelblat–Jouyban–Acree model, Ma and Sun models.
Section snippets
Materials
Limonin (mass-fraction purity ⩾ 0.98) was isolated from E. fructus previously in our laboratory, its chemical structure was confirmed by 1H NMR (Fig. S1) which was consistent with the data in the literature [18], [19], [20]. Methanol and acetone were analytical reagents and were purchased from Tianjin Hengxin Chemical Preparation Co. Ltd. (Tianjin, China) and Shanghai Rich Joint Chemical Reagents Co. Ltd. (Shanghai, China), respectively. Doubly distilled water was prepared from a SZ-93 automatic
Characterization of limonin
The representative PXRD patterns of limonin standard and precipitates in different solvents were presented in Fig. 2 (Supporting Information). Compared with the PXRD pattern of limonin standard, the PXRD patterns of the precipitates in each solvent exhibited no significant changes, indicating that limonin had no polymorphism throughout the experiments.
Solubility values
The mole fraction solubility of limonin along with the standard uncertainties in methanol aqueous solution and acetone aqueous solution are
Conclusions
The solubility of limonin in the methanol aqueous solution and acetone aqueous solution were measured at different temperatures ranging from 283.2 K to 318.2 K. The solubility of limonin increased with increasing temperature in the two aqueous solutions. The solubility of limonin increased with increasing methanol in the methanol aqueous solution, whereas the maximum point in acetone + water binary solvent mixtures was observed at 0.9 mol fraction of acetone. To correlate the solubility with
Acknowledgments
Financial support from the National Natural Science Foundation of China (Nos. 21366019, 20806037 and 20876131), Jiangxi Province Young Scientists (Jinggang Star) Cultivation Plan (20112BCB23002), Jiangxi Province Higher School Science and Technology Landing Plan Projects (No. KJLD13012), Special Funds for Graduate Student Innovation in Jiangxi Province (No. YC2014-S013), and Jiangxi Province Undergraduate Innovation and Entrepreneurship Training Program (No. 201310403040) are gratefully
References (44)
- et al.
Biomed. Prev. Nutr.
(2013) - et al.
Eur. J. Pharmacol.
(2014) - et al.
Bioorg. Med. Chem. Lett.
(2014) - et al.
J. Chem. Thermodyn.
(2013) - et al.
J. Chem. Thermodyn.
(2015) - et al.
J. Mol. Liq.
(2016) - et al.
J. Chem. Thermodyn.
(2013) - et al.
J. Chem. Thermodyn.
(2012) - et al.
J. Chem. Thermodyn.
(2015) - et al.
J. Chem. Thermodyn.
(2015)
Fluid Phase Equilib.
Food Chem.
J. Chem. Thermodyn.
J. Chem. Thermodyn.
J. Chem. Thermodyn.
J. Mol. Liq.
J. Mol. Liq.
J. Mol. Liq.
J. Chem. Thermodyn.
J. Chem. Thermodyn.
Rapid Commun. Mass Spectrom.
Chem. Biodivers.
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