Measurement and correlation of the solubility of genistin in eleven organic solvents from T = (283.2 to 323.2) K
Graphical abstract
Introduction
Genistin (C21H20O10, Molar mass: 432.37 g · mol−1, CAS number: 529-59-9, figure 1) is one of the most effective isoflavone in soybean or Radix Puerariae Lobatae. Chemically, it is the 7-O-β-d-glucoside form of genistein. Genistin has attracted much attention due to its wide variety of pharmacological activities, such as weak oestrogen activity [1], antioxidant activity [2], [3], hemolysis activity and antibacterial activity [4]. It is also considered as an effectual preventive for breast cancer [5], colon cancer [6], osteoporosis [7] and so on. Therefore, Genistin is often used as dietary supplements [8]. In soybean and Radix Puerariae some other similar isoflavones, i.e. daidein and genistein, coexist with genistin. In order to separate and purify them, it is necessary to understand their solubilities in various solvents. In the literatures, the solubilities of daidein [9], [10] and genistein [11] have been reported. However, the solubility of genistin has not been systematically studied. So, in this research the solubility data of genistin and the thermodynamic parameter (Gibbs free energy, enthalpy and entropy) in various solvents were reported.
Section snippets
Materials
Genistin (mass fraction purity ⩾ 0.98) was purchased from Xi’an Haoxuan Biotechnology Co. Ltd, Shanxi, China (table 1), and used without further treatment. Its structure was confirmed by UV and 1HNMR spectra. The source and the purity of all the organic solvents were listed in table 1.
Solubility measurement
The solubility of genistin was measured by the HPLC analysis method according to the literatures [12], [13] with minor modification. The experimental saturated solutions were prepared in a glass vial by adding
Evaluation of thermochemical properties
The thermal analysis (TGA/DSC) of genistin was shown in figure 2. According to the DSC analysis, the determined melting point (Tm) of genistin was T = 547.47 K, and the determined molar fusion enthalpy (ΔfusHm) of genistin was 65.6 kJ · mol−1. The standard uncertainty of the melting point value was T = 0.01 K, and the relative standard uncertainty of the calorimetric measurement was 0.02. In this study, the initial melting temperature of genistin was 537.15 K according to the DSC curve, however the
Conclusion
The solubility of genistin in eleven organic solvents was measured from T = (283.2 to 323.2) K, at a given temperature in the range of (283.2 K to 323.2) K, the order of the solubility of genistin is acetone > tetrahydrofuran > methanol > ethanol > isopropanol > n-butyl alcohol > acetonitrile ≈ ethyl acetate > cyclohexane ≈ n-hexane > chloroform. The polarities and hydrogen bond abilities of the solvents played an important role in the dissolution process. Four thermodynamic models were applied to correlate the
Acknowledgment
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 (35)
- et al.
Maturitas
(2008) - et al.
Food Chem.
(2009) - et al.
Food Chem.
(2005) - et al.
Bioch. Biophys. Acta
(2013) - et al.
J. Nutr. Biochem.
(2000) - et al.
Fluid Phase Equilib.
(2014) - et al.
J. Mol. Liq.
(2013) - et al.
J. Chem. Thermodyn.
(2013) - et al.
Fluid Phase Equilib.
(2013) - et al.
Food Chem.
(2011)
Food Res. Int.
J. Pharm. Sci.
J. Chem. Thermodyn.
J. Chem. Thermodyn.
Fluid Phase Equilib.
J. Chem. Thermodyn.
Fluid Phase Equilib.
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