Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol

Dae-won Chung; Young Tai Choi

Journal of Industrial and Engineering Chemistry, Vol.13, No.3, 367-372, May, 2007

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Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol

Dae-won Chung^†, and Young Tai Choi

Department of Polymer Engineering, College of Engineering, Suwon University, Suwon 400-600, Korea

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In this study, hydrophilic derivatives of β-sitosterol, which is known to have potential to reduce blood cholesterol levels, were synthesized by the esterification of poly(ethylene glycol) (PEG) and β-sitosterol with carboxylic functionality in the presence of dehydrating agents and a basic catalyst. By adjusting the molar ratios of reactants in the esterification reaction, hydrophilic β-sitosterol derivatives (HPSs) with various degrees of substitution (DS, average molar number of β-sitosterol moieties per molecule of HPS) were synthesized. The chemical structure and the distribution of isomers in HPSs were characterized by 1H-NMR spectroscopy and MALDI-TOF mass spectrometry, respectively. The solubility of HPS in water was significantly affected by the value of DS of HPS.

Keywords:β-sitosterol;hydrophilic derivatives;poly(ethylene glycol);esterification

[References]

Vanhanen HT, Miettinen TA, Clin. Chim. Acta, 205, 97 (1992)
Gylling H, Miettinen TA, J. Lipid Res., 37, 1776 (1996)
Jones PJH, MacDougall DE, Ntanios F, Vanstone CA, Can. J. Physiol. Pharmacol., 75, 217 (1997)
U. S. Patent 6,184,397 (2001)
Mattson FH, Volpenhein RA, Martin JB, J. Lipid Res., 5, 374 (1964)
Pinter KG, Hamilton JG, Muldrey JE, J. Lipid Res., 5, 273 (1964)
Chung DW, Cho YT, J. Korean Ind. Eng. Chem., 17(4), 375 (2006)
U. S. Patent 6,660,491 (2003)
Jones PJH, MacDougall DE, Ntanios F, Vanstone CA, Can, J. Pharmacol., 75, 217 (1997)
U. S. Patent 5,502,045 (1996)
Weststrate JA, Meijer GW, Eur. J. Clin. Nutr., 52, 334 (1998)
U. S. Patent 5,215,759 (1993)
Ding WX, Qi XR, Li P, Maitani Y, Nagai T, Int. J. Pharm., 300, 38 (2005)
Skornick YG, Rong GH, Sindelar WF, Richert L, Klausner JM, Rozin RR, Shinitzky M, Cancer, 58, 650 (1986)
Yuan XB, Li H, Yuan YB, Carbohydr. Polym., 65, 337 (2006)
Kuhn RW, Schrader WT, Smith RG, O’Malley BW, J. Biol. Chem., 250, 4220 (1975)
Pouchert CJ, Behnke J, The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc. (1993)
Mun SP, Hassan EM, Yoon TH, J. Korean Ind. Eng. Chem., 7, 430 (2001)
Mun SP, Gilmour IA, Jordan PJ, J. Ind. Eng. Chem., 12(5), 720 (2006)
Lee SB, Park KA, Hong IK, J. Korean Ind. Eng. Chem., 10(3), 438 (1999)
Paquette LA, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester (1995)

[Referenced By]

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[1] Vanhanen HT, Miettinen TA, Clin. Chim. Acta, 205, 97 (1992)

[2] Gylling H, Miettinen TA, J. Lipid Res., 37, 1776 (1996)

[3] Jones PJH, MacDougall DE, Ntanios F, Vanstone CA, Can. J. Physiol. Pharmacol., 75, 217 (1997)

[4] U. S. Patent 6,184,397 (2001)

[5] Mattson FH, Volpenhein RA, Martin JB, J. Lipid Res., 5, 374 (1964)

[6] Pinter KG, Hamilton JG, Muldrey JE, J. Lipid Res., 5, 273 (1964)

[7] Chung DW, Cho YT, J. Korean Ind. Eng. Chem., 17(4), 375 (2006)

[8] U. S. Patent 6,660,491 (2003)

[9] Jones PJH, MacDougall DE, Ntanios F, Vanstone CA, Can, J. Pharmacol., 75, 217 (1997)

[10] U. S. Patent 5,502,045 (1996)

[11] Weststrate JA, Meijer GW, Eur. J. Clin. Nutr., 52, 334 (1998)

[12] U. S. Patent 5,215,759 (1993)

[13] Ding WX, Qi XR, Li P, Maitani Y, Nagai T, Int. J. Pharm., 300, 38 (2005)

[14] Skornick YG, Rong GH, Sindelar WF, Richert L, Klausner JM, Rozin RR, Shinitzky M, Cancer, 58, 650 (1986)

[15] Yuan XB, Li H, Yuan YB, Carbohydr. Polym., 65, 337 (2006)

[16] Kuhn RW, Schrader WT, Smith RG, O’Malley BW, J. Biol. Chem., 250, 4220 (1975)

[17] Pouchert CJ, Behnke J, The Aldrich Library of 13C and 1H FT NMR Spectra, Aldrich Chemical Company, Inc. (1993)

[18] Mun SP, Hassan EM, Yoon TH, J. Korean Ind. Eng. Chem., 7, 430 (2001)

[19] Mun SP, Gilmour IA, Jordan PJ, J. Ind. Eng. Chem., 12(5), 720 (2006)

[20] Lee SB, Park KA, Hong IK, J. Korean Ind. Eng. Chem., 10(3), 438 (1999)

[21] Paquette LA, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester (1995)