Preferential Solvation of the Antioxidant Agent Daidzein in some Aqueous Co-Solvent Mixtures according to IKBI and QLQC Methods


  • Daniel M. Jiménez Universidad Nacional de Colombia
  • Zaira J. Cárdenas Universidad Nacional de Colombia
  • Daniel R. Delgado Universidad Cooperativa de Colombia
  • María Á. Peña Universidad de Alcalá
  • Fleming Martínez Universidad Nacional de Colombia



Daidzein, ethanol, propylene glycol, preferential solvation, inverse Kirkwood-Buff integrals, quasi-lattice-quasi-chemical


The preferential solvation parameters by ethanol (EtOH) or propylene glycol (PG) of daidzein were derived from their solution thermodynamic properties by means of the inverse Kirkwood-Buff integrals and the quasi-lattice-quasi-chemical (QLQC) methods. According to IKBI method, the preferential solvation parameter by the co-solvent, δx1,3, is negative in water-rich mixtures but positive in co-solvent-rich mixtures in both kinds of systems. This could demonstrate the relevant role of hydrophobic hydration around the aromatic rings in the drug solvation in water-rich mixtures. Furthermore, the more solvation by co-solvent in co-solvent-rich mixtures could be due mainly to polarity effects and acidic behavior of the hydroxyl groups of the compound in front to the more basic solvents present in the mixtures, i.e. EtOH or PG. Otherwise, according to QLQC method, this drug is preferentially solvated by the co-solvents in all the mixtures in both kind of systems.


[1] Liggins J, Bluck LJ, Runswick S, Atkinson C, Coward WA, Bingham SA. Daidzein and genistein contents of vegetables. Br J Nutr 2000; 84: 717-25.
[2] Coward L, Barnes NC, Setchell KDR, Barnes S. Genistein, daidzein, and their -glycoside conjugates: Antitumor isoflavones in soybean foods from American and Asian diets. J Agric Food Chem 1993; 41: 1961-7.
[3] Budavari S, O’Neil MJ, Smith A, Heckelman PE, Obenchain, Jr. JR, Gallipeau JAR, D’Arecea MA, Eds. The Merck index: An encyclopedia of chemicals, drugs, and biologicals. 13th ed. Whitehouse Station, NJ: Merck & Co., Inc.; 2001.
[4] Liang J, Tian YX, Fu LM, Wang TH, Li HJ, Wang P, Han RM, Zhang JP, Skibsted LH. Daidzein as an antioxidant of lipid: effects of the microenvironment in relation to chemical structure. J Agric Food Chem 2008; 56: 10376-83.
[5] Jouyban A. Handbook of solubility data for pharmaceuticals. Boca Raton, FL: CRC Press; 2010.
[6] Rubino JT. Cosolvents and cosolvency. In: Swarbrick J, Boylan JC, editors. Encyclopedia of pharmaceutical technology. Vol 3. New York, NY: Marcel Dekker, Inc. 1988; p. 375-98.
[7] Yalkowsky SH. Solubility and solubilization in aqueous media. New York, NY: American Chemical Society and Oxford University Press; 1999.
[8] Yang G-D, Huang Y-R, Nan G-J, Chen H-J, Zeng A-G, Bian X-L. Solubility of daidzein in the binary system of ethanol and water. J Mol Liq 2013; 180: 160-3.
[9] Zeng A-G, Pang X-L, Wu N, Wang D, Nan G-J, Yang G-D, Bian X-L. Solubility of daidzein in propylene glycol plus water cosolvent mixtures. Fluid Phase Equilib 2014; 366: 127-33.
[10] Aulton ME. Pharmaceutics: The science of dosage forms design. 2nd ed. London: Churchill Livingstone; 2002.
[11] Smolinske SC. Handbook of drug, food and cosmetic excipients. Boca Raton, FL: CRC Press LLC; 1992.
[12] Anwer MK, Al-Shdefat R, Jamil Sh, Alam P, Abdel-Kader MS, Shakeel F. Solubility of bioactive compound hesperidin in six pure solvents at (298.15 to 333.15) K. J Chem Eng Data 2014; 59: 2065-9.
[13] Shakeel F, Haq N, Siddiqui NA. Solubility and thermodynamic function of vanillin in ten different environmentally benign solvents. Food Chem 2015; 180: 244-8.
[14] Marcus Y. Solvent mixtures: Properties and selective solvation. New York, NY: Marcel Dekker, Inc.; 2002.
[15] Marcus Y. Preferential solvation of ibuprofen and naproxen in aqueous 1,2-propanediol. Acta Chim Sloven 2009; 56: 40-4.
[16] Marcus Y. Preferential solvation in mixed solvents. In: Smith PE, Matteoli E, O’Connell JP, editors. Fluctuation theory of solutions: Applications in chemistry, chemical engineering, and biophysics. Boca Raton, FL: CRC Press, Taylor & Francis Group 2013; p. 65-92.
[17] Cárdenas ZJ, Jiménez DM, Martínez F. Preferential solvation of ketoprofen in some co-solvent binary mixtures. J Solution Chem 2014; 43: 1904-15.
[18] Marcus Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J Mol Liq 2008; 140: 61-7.
[19] Delgado DR, Martínez F. Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method. J Mol Liq 2014; 193: 152-9.
[20] Jiménez DM, Cárdenas ZJ, Delgado DR, Martínez F, Jouyban A. Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K. Phys Chem Liq 2014; 52: 726-37.
[21] Peña MÁ, Delgado DR, Martínez F. Preferential solvation of acetaminophen in propylene glycol + water co-solvent mixtures. J Appl Sol Chem Model 2014; 3: 65-73.
[22] Delgado DR, Peña MÁ, Martínez F. Preferential solvation of some sulfonamides in propylene glycol + water solvent mixtures according to the IKBI and QLQC methods. J Solution Chem 2014; 43: 360-74.
[23] Fedors RF. A method for estimating both the solubility parameters and molar volumes of liquids. Polym Eng Sci 1974; 14: 147-54.
[24] Jiménez J, Manrique J, Martínez F. Effect of temperature on some volumetric properties for ethanol + water mixtures. Rev Colomb Cienc Quím Farm 2004; 33: 145-55.
[25] Jiménez J, Martínez F. Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures. Rev Colomb Cienc Quím Farm 2005; 34: 46-57.
[26] Kamlet MJ, Taft RW. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 1976; 98: 377-83.
[27] Marcus Y. The properties of solvents. Chichester, UK: John Wiley & Sons; 1998.
[28] Holguín AR, Delgado DR, Martínez F, Marcus Y. Solution thermodynamics and preferential solvation of meloxicam in propylene glycol + water mixtures. J Solution Chem 2011; 40: 1987-99.
[29] Barton AFM. Handbook of solubility parameters and other cohesion parameters. 2nd ed. BocaRaton, FL: CRC Press LLC; 1991.
[30] Delgado DR, Martínez F. Preferential solvation of some structurally related sulfonamides in 1-propanol + water cosolvent mixtures. Phys Chem Liq 2015; 53: 293-306.






General Articles