Solubility prediction of bioantioxidants for functional solvent by group contribution method

Kyung Ai Park; Hyoung Jin Lee; In Kwon Hong

Journal of Industrial and Engineering Chemistry, Vol.16, No.3, 490-495, May, 2010

DOI10.1016/j.jiec.2010.01.060 Export Citation

Solubility prediction of bioantioxidants for functional solvent by group contribution method

Kyung Ai Park, Hyoung Jin Lee¹, and In Kwon Hong^{1, †}

Seoul Metropolitan Government Research Institute of Public Health and Environment, 427-070, Republic of Korea
¹Department of Chemical Engineering, Dankook University, 448-701, Republic of Korea

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Bioantioxidants protect a living body from the damage and ageing caused by active oxygen. Typical bioantioxidants include epicatechin, caffeic acid, ascorbic acid, etc. This study focused on selecting the optimum solvent that can dissolve each bioantioxidants by calculating the solubility of various bioantioxidants in each specific solvent. The solubility parameters of the bioantioxidants were correlated with the van Krevelen group model, and the solubility of bioantioxidant for each solvent was then calculated from the interaction relationship between each solubility parameter of the bioantioxidant and optimal solvent selected. The solubility of the bioantioxidants was affected not only by the solubility parameters of the solute and solvents, but also by the fusion enthalpy of the solute at melting temperature. Then the fusion enthalpy was measured for each bioantioxidant. The equilibrium non-ideality between the solvent and bioantioxidants examined as a function of the solubility parameter and fusion enthalpy. The optimum solvent was selected for each bioantioxidant based on the quantitative solubility data. Each bioantioxidant showed slight non-ideality, which it was presented in the activity coefficient of the solution system.

Keywords:Bioantioxidants;Group contribution;Solubility parameter;Optimum solvent;Fusion enthalpy

[References]

Choi HS, Lee MJ, Na MS, Lee MY, Choi DB, J. Ind. Eng. Chem., 15(2), 275 (2009)
Adelman R, Saul RL, Ames BN, Proc. Natl. Acad. Sci. U.S.A., 85, 2706 (1989)
Ames BN, Science., 221, 1256 (1983)
Amstad P, Cerutti D, Environ. Health Perspect., 88, 77 (1990)
Lee HJ, Hong IK, J. Korean Ind. Eng. Chem., 20(3), 346 (2009)
Kang JH, Chung ST, Row KH, J. Ind. Eng. Chem., 8(4), 354 (2002)
Charles M. Hansen, Hansen Solubility Parameter: A User Hand Book, CRC Press, Boca Raton (1999)
O¨ zdemir C, Gu¨ ner A, Eur. Polym. J., 43, 3068 (2007)
Verheyen S, Augustijns P, Kinget R, Van den Mooter G, Int. J. Pharm., 228, 199 (2001)
Prausnitz JM, Lichtenthaler RN, de Azevedo EG, Molecular Thermodynamics of Fluid-phase Equilibria, PTR, Prentice Hall, NJ (1999)
De Nervers N, Physical and Chemical Equilibrium for Chemical Engineers, John Wiley & Sons, New York (2002)
Hireschfelder JO, Curtiss CF, Bird RB, Molecular Theory of Gasses and Liquids, John Wiley & Sons, New York (1964)
Goharshadi EK, Hesabi M, J. Mol. Liquids., 113, 125 (2004)
Terada M, Marchessault RH, Int. J. Biol. Macromol., 25, 207 (1999)
Adamsk K, Voelkel A, He´ berger K, J. Chromatogr. A., 1171, 90 (2007)
van Krevelen DW, The Properties of Polymer, Elsevier, New York (1990)
Gu¨ ner A, Eur. Polym. J., 40, 1587 (2004)
Ravindra R, Krovvidi KR, Khan AA, Carbohydr. Polym., 36, 121 (1998)
Back DD, Grzyll LR, Corrigan M, Thermochim. Acta, 272, 53 (1996)
Forster A, Hempenstall J, Tucker I, Rades T, Int. J. Pharm., 226, 147 (2001)

[Referenced By]

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[1] Choi HS, Lee MJ, Na MS, Lee MY, Choi DB, J. Ind. Eng. Chem., 15(2), 275 (2009)

[2] Adelman R, Saul RL, Ames BN, Proc. Natl. Acad. Sci. U.S.A., 85, 2706 (1989)

[3] Ames BN, Science., 221, 1256 (1983)

[4] Amstad P, Cerutti D, Environ. Health Perspect., 88, 77 (1990)

[5] Lee HJ, Hong IK, J. Korean Ind. Eng. Chem., 20(3), 346 (2009)

[6] Kang JH, Chung ST, Row KH, J. Ind. Eng. Chem., 8(4), 354 (2002)

[7] Charles M. Hansen, Hansen Solubility Parameter: A User Hand Book, CRC Press, Boca Raton (1999)

[8] O¨ zdemir C, Gu¨ ner A, Eur. Polym. J., 43, 3068 (2007)

[9] Verheyen S, Augustijns P, Kinget R, Van den Mooter G, Int. J. Pharm., 228, 199 (2001)

[10] Prausnitz JM, Lichtenthaler RN, de Azevedo EG, Molecular Thermodynamics of Fluid-phase Equilibria, PTR, Prentice Hall, NJ (1999)

[11] De Nervers N, Physical and Chemical Equilibrium for Chemical Engineers, John Wiley & Sons, New York (2002)

[12] Hireschfelder JO, Curtiss CF, Bird RB, Molecular Theory of Gasses and Liquids, John Wiley & Sons, New York (1964)

[13] Goharshadi EK, Hesabi M, J. Mol. Liquids., 113, 125 (2004)

[14] Terada M, Marchessault RH, Int. J. Biol. Macromol., 25, 207 (1999)

[15] Adamsk K, Voelkel A, He´ berger K, J. Chromatogr. A., 1171, 90 (2007)

[16] van Krevelen DW, The Properties of Polymer, Elsevier, New York (1990)

[17] Gu¨ ner A, Eur. Polym. J., 40, 1587 (2004)

[18] Ravindra R, Krovvidi KR, Khan AA, Carbohydr. Polym., 36, 121 (1998)

[19] Back DD, Grzyll LR, Corrigan M, Thermochim. Acta, 272, 53 (1996)

[20] Forster A, Hempenstall J, Tucker I, Rades T, Int. J. Pharm., 226, 147 (2001)