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Articles

Solution thermodynamics and preferential solvation of hesperidin in aqueous cosolvent mixtures of ethanol, isopropanol, propylene glycol, and n-propanol

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Pages 432-444 | Received 18 Apr 2018, Accepted 20 May 2018, Published online: 06 Jun 2018

References

  • Rubino JT. Cosolvents and cosolvency. In: Swarbrick J, JC B, editors. Encyclopedia of pharmaceutical technology. Vol. 3. New York (NY): Marcel Dekker, Inc.; 1988. p. 375–398.
  • Jouyban A. Handbook of solubility data for pharmaceuticals. Boca Raton (FL): CRC Press; 2010.
  • Martinez F, Jouyban A, Acree WE Jr. Pharmaceuticals solubility is still nowadays widely studied everywhere (editorial). Pharm Sci (Tabriz). 2017;23:1–2.
  • Marcus Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J Mol Liq. 2008;140:61–67.
  • Marcus Y. Preferential solvation of drugs in binary solvent mixtures. Pharm Anal Acta. 2017;8:1000537.
  • Budavari S, O’Neil MJ, Smith A. et al., The merck index: an encyclopedia of chemicals, drugs, and biologicals. 13th ed. 833–834. Whitehouse Station (NJ): Merck & Co., Inc.; 2001.
  • Laszlo P. Citrus: a history. Chicago: University of Chicago Press; 2007.
  • Xu R, Cong Y, Zheng M, et al. Solubility and modeling of hesperidin in cosolvent mixtures of ethanol, isopropanol, propylene glycol, and n-propanol + water. J Chem Eng Data. 2018;63:764–770.
  • Barton AFM. Handbook of Solubility Parameters and Other Cohesion Parameters. 2nd ed. New York (NY): CRC Press; 1991.
  • Marcus Y. The Properties of Solvents. Chichester (UK): John Wiley & Sons; 1998.
  • Bustamante P, Romero S, Peña A, et al. Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water. J Pharm Sci. 1998;87:1590–1596.
  • Martínez F, Peña MA, Bustamante P. Thermodynamic analysis and enthalpy-entropy compensation for the solubility of indomethacin in aqueous and non-aqueous mixtures. Fluid Phase Equilib. 2011;308:98–106.
  • Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 1. Some fundamental statistical problems associated with the analysis of van’t Hoff and Arrhenius data. J Phys Chem. 1976;80:2335–2341.
  • Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effect. J Phys Chem. 1976;80:2341–2351.
  • Delgado DR, Rodríguez GA, Martínez F. Thermodynamic study of the solubility of sulfapyridine in some ethanol + water mixtures. J Mol Liq. 2013;177:156–161.
  • Jiménez DM, Cárdenas ZJ, Delgado DR, et al. Solubility temperature dependence and preferential solvation of sulfadiazine in 1,4-dioxane + water co-solvent mixtures. Fluid Phase Equilib. 2015;397:26–36.
  • Jiménez DM, Cárdenas ZJ, Martínez F. Solubility and solution thermodynamics of meloxicam in polyethylene glycol 400 + water mixtures. J Mol Liq. 2015;211:233–238.
  • Romero S, Reillo A, Escalera B, et al. The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents: relationship of solubility curves to specific and nonspecific interactions. Chem Pharm Bull. 1996;44:1061–1064.
  • Perlovich GL, Kurkov SV, Kinchin AN, et al. Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs. Eur J Pharm Biopharm. 2004;57:411–420.
  • Marcus Y. Solvent Mixtures: properties and Selective Solvation. New York (NY): Marcel Dekker, Inc.; 2002. p. 180–238.
  • Nozohouri S, Shayanfar A, Cárdenas ZJ, et al. Solubility of celecoxib in N-methyl-2-pyrolidone + water mixtures at various temperatures: experimental data and thermodynamic analysis. Kor J Chem Eng. 2017;34:1435–1443.
  • Jiménez DM, Cárdenas ZJ, Delgado DR, et al. Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K. Phys Chem Liq. 2014;52:726–737.
  • Jouyban A, Acree WE Jr, Martínez F. Modelling the solubility and preferential solvation of gallic acid in cosolvent + water mixtures. J Mol Liq. 2016;224:502–506.
  • Martínez F, Jouyban A, Acree WE Jr. Solubility of phenobarbital in aqueous cosolvent mixtures revisited: IKBI preferential solvation analysis. Phys Chem Liq. 2017;55:432–443.
  • Fedors RF. A method for estimating both the solubility parameters and molar volumes of liquids. Polym Eng Sci. 1974;14:147–154.
  • Ben-Naim A. Preferential solvation in two- and in three-component systems. Pure Appl Chem. 1990;62:25–34.
  • Marcus Y. Solubility and solvation in mixed solvent systems. Pure Appl Chem. 1990;62:2069–2076.
  • Kamlet MJ, Taft RW. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc. 1976;98:377–383.
  • Apelblat A, Manzurola E. Solubilities of o-acetylsalicylic, 4-aminosalicylic, 3,5-dinitrosalicylic, and p-toluic acid, and magnesium-DL-aspartate in water from T = (278 to 348) K. J Chem Thermodyn. 1999;31:85–91.
  • Jouyban A, Acree WE Jr. Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures. J Mol Liq. 2018;256:541–547.
  • Vahdati S, Shayanfar A, Hanaee J, et al. Solubility of carvedilol in ethanol+ propylene glycol mixtures at various temperatures. Ind Eng Chem Res. 2013;52:16630–16636.
  • Jouyban A, Khoubnasabjafari M, Chan HK, et al. Solubility prediction of anthracene in mixed solvents using a minimum number of experimental data. Chem Pharm Bull. 2002;50:21–25.
  • Jouyban A, Soltanpour S, Soltani S, et al. Prediction of drug solubility in mixed solvents using computed Abraham parameters. J Mol Liq. 2009;146:82–88.
  • Acree WE Jr, Grubbs LM, Abraham MH. Prediction of partition coefficients and permeability of drug molecules in biological systems with Abraham model solute descriptors derived from measured solubilities and water-to-organic solvent partition coefficients. In: WE Jr A, editor. Toxicity and Drug Testing. London: IntechOpen; 2012.
  • Stovall D, Givens C, Keown S, et al. Solubility of crystalline nonelectrolyte solutes in organic solvents: mathematical correlation of ibuprofen solubilities with the Abraham solvation parameter model. Phys Chem Liq. 2005;43:261–268.
  • Stovall DM, Dai C, Zhang S, et al. Abraham model correlations for describing solute transfer into anhydrous 1, 2-propylene glycol for neutral and ionic species. Phys Chem Liq. 2016;54:1–13.
  • Schmidt A, Grover D, Zettl H, et al. Determination of Abraham model solute descriptors for isophthalic acid from experimental solubility data in organic solvents at 298 K. Phys Chem Liq. 2016;54:747–757.
  • PharmaAlgorithms. ADME boxes, version 3.0. Canada: PharmaAlgorithms Inc., 591 Indian Road, Toronto, ON M6P 2C4; 2006.

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