Determination and Correlation of Solubility of Nonivamide in Different Solvents

doi:10.1016/j.cjche.2013.05.001

Abstract

Abstract: The solubility of nonivamide in dimethyl sulfoxide,methanol, acetone, ethyl acetate,methyl tert-butyl ether, acetonitrile, n-hexane and water over the temperature range of 293.2 K to 323.2 K wasmeasured. The results reveal that the solubility of nonivamide is greatly influenced by the hydrogen-bond basicity of solvent and increases with temperature. The experimental data were correlated with the modified Apelblat equation. The dissolution enthalpy and entropy of nonivamide in different solvents were obtained from the correlation of lnx with 1/T using the van't Hoff equation. The calculated nonivamide solubility is in good agreement with experimental data for most of the solvents.

Key words: Solubility, Nonivamide, Hydrogen-bonding interaction, Modified Apelblat equation, van't Hoff plotting

摘要： The solubility of nonivamide in dimethyl sulfoxide,methanol, acetone, ethyl acetate,methyl tert-butyl ether, acetonitrile, n-hexane and water over the temperature range of 293.2 K to 323.2 K wasmeasured. The results reveal that the solubility of nonivamide is greatly influenced by the hydrogen-bond basicity of solvent and increases with temperature. The experimental data were correlated with the modified Apelblat equation. The dissolution enthalpy and entropy of nonivamide in different solvents were obtained from the correlation of lnx with 1/T using the van't Hoff equation. The calculated nonivamide solubility is in good agreement with experimental data for most of the solvents.

关键词: Solubility, Nonivamide, Hydrogen-bonding interaction, Modified Apelblat equation, van't Hoff plotting

Yifeng Cao, Qiwei Yang, Huabin Xing, Zongbi Bao, Baogen Su, Yiwen Yang, Qilong Ren. Determination and Correlation of Solubility of Nonivamide in Different Solvents[J]. , 2014, 22(10): 1141-1144.

References

[1] H.L. Constant, G.A. Cordell, Nonivamide, a constituent of capsicum oleoresin, J. Nat. Prod. 59 (1996) 425-426.
[2] J.Y. Fang, Y.L. Leu, Y.Y. Wang, Y.H. Tsai, In vitro topical application and in vivo pharmacodynamic evaluation of nonivamide hydrogels using Wistar rat as an animal model, Eur. J. Pharm. Sci. 15 (2002) 417-423.
[3] A. Rosa, G. Appendino, M.P. Melis, M. Deiana, A. Atzeri, I. Alessandra, A. Minassi, M.A. Dessi, Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation, Chem. Biol. Interact. 180 (2009) 183-192.
[4] J.L. Yeh, Y.C. Lo, Y. Wang, I.J. Chen, Cardiovascular interactions of nonivamide, glyceryl nonivamide, capsaicin analogues, and substance P antagonist in rats, Brain Res. Bull. 30 (1993) 641-648.
[5] J.Y. Fang, C.L. Fang, C.T. Hong, H.Y. Chen, T.Y. Lin, H.M. Wei, Capsaicin and nonivamide as novel skin permeation enhancers for indomethacin, Eur. J. Pharm. Sci. 12 (2001) 195-203.
[6] S.M. Walas, Phase Equilibria in Chemical Engineering, Butterworth-Heinemann, New York, 1985.
[7] W. Chen, B.G. Su, H.B. Xing, Y.W. Yang, Q.L. Ren, Solubility of desmosterol in five organic solvents, J. Chem. Eng. Data 53 (2008) 2715-2717.
[8] W. Chen, B.G. Su, H.B. Xing, Y.W. Yang, Q.L. Ren, Solubilities of cholesterol and desmosterol in binary solvent mixtures of n-hexane + ethanol, Fluid Phase Equilib. 287 (2009) 1-6.
[9] S.P. Pinho, E.A. Macedo, Solubility of NaCl, NaBr, and KCl in water, methanol, ethanol, and their mixed solvents, J. Chem. Eng. Data 50 (2005) 29-32.
[10] M.J. Kamlet, J.L.M. Abbound, M.H. Abraham, R.W. Taft, Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π^*, α, and β, and some methods for simplifying the generalized solvatochromic equation, J. Org. Chem. 48 (1983) 2877-2887.
[11] M.H. Abraham, J. Andonian-Haftvan, G.S. Whiting, A. Leo, R.S. Taft, Hydrogen bonding. Part 34. The factors that influence the solubility of gases and vapors in water at 298 K, and a new method for its determination, J. Chem. Soc. Perkin Trans. 2 (8) (1994) 1777-1791.
[12] A. Apelblat, E. Manzurola, 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. 31 (1999) 85-91.
[13] R.S. Liang, Z.B. Bao, B.G. Su, H.B. Xing, Q.L. Ren, Solubility of Vitamin D3 in six organic solvents at temperatures from (248.2 to 273.2) K, J. Chem. Eng. Data 57 (2012) 2328-2331.
[14] D.W.Wei, Y.H. Pei, Measurement and correlation of solubility of diphenyl carbonate in alkanols, Ind. Eng. Chem. Res. 47 (2008) 8953-8956.
[15] D.H.M. Beiny, J.W. Muiiln, Solubilities of higher normal alkanes in m-xylene, J. Chem. Eng. Data 32 (1987) 9-10.