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Hydrolysis of nonionic ester surfactants facilitated by potassium β-glycyrrhizinate: Implication of catalytic functions played by the carboxyl groups

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Journal of the American Oil Chemists' Society

Abstract

Two different types of methyl esters of β-glycyrrhizinate (GK2) have been prepared to delineate the mechanism of the catalytic action of each carboxyl group of GK2 in the hydrolysis of nonionic fatty acid surfactants. In the acidic pH region of less than 4, the hydrolysis is catalyzed by the carboxyl groups of the sugar moiety, while in the close-to-neutral acidic region, the carboxyl group at the hydrophobic triterpenoid end becomes important in catalysis.

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References

  1. Maruzen Pharmaceuticals Co., Ltd., Dipotassium Glycyrrhizinate, 1994, May.

  2. Tamagaki, S., M. Koide, M. Takahashi, T. Mizushima, J. Ukawa, and W. Tagaki, Inhibitory Effect of Cyclodextrins by Inclusion on the Catalytic Activity of Glycyrrhizinate for the Hydrolysis of a Nonionic Ester Surfactant, J. Chem. Soc., Perkin Trans. 2:1257–1260 (1996).

    Google Scholar 

  3. Koide, M., S. Tamagaki, M. Takahashi, and W. Tagaki, Catalytic Effect of Dipotassium Glycyrrhzinate on the Hydrolysis of Nonionic Ester Surfactants, J. Am. Oil Chem. Soc. 73:913–920 (1996).

    Article  CAS  Google Scholar 

  4. Maitani, Y., T. Ishikura, and T. Nagai, Drug Effect and Surface Chemistry, Yakugaku 37:408–415 (1988).

    CAS  Google Scholar 

  5. Aoki, K., H. Fujisawa, and J. Ise, Hydrolysis of Nonionic Surfactants, Ann. Rept. Takeda Res. Lab. 27:172–176 (1968).

    CAS  Google Scholar 

  6. Murata, T., Y. Kikuchi, T. Kurazumi, K. Imamori, and A. Iwasa, Stability of Polyoxyethylene(60) Hydrogenated Castor Oil in Aqueous Solution, Yakuzaigaku 50:15–22 (1990).

    CAS  Google Scholar 

  7. Saito, Y., and T. Sato, Micellar Formation and Micellar Structure of Poly(oxyethylene) Hydrogenated Castor Oil, Yakugaku Zasshi 112:763–767 (1992).

    PubMed  CAS  Google Scholar 

  8. Koide, M., J. Ukawa, A. Odaka, W. Tagaki, and S. Tamagaki, Amphiphilic Aspects and Micellar Structures of Anti-inflammatory Agents α- and β-Glycyrrhizinate, J. Jpn. Oil Chem. Soc. 45:1339–1347 (1996).

    CAS  Google Scholar 

  9. Otsuka, A., Y. Yonezawa, K. Iba, K. Takatsu, and K. Sunada, Physico-Chemical Properties of Glycyrrhizic Acid in Aqueous Media. I. Surface-Active Properties and Formation of Molecular Aggregates, Ibid.:203–208 (1976).

    CAS  Google Scholar 

  10. Ingold, C.K., Structure and Mechanism in Organic Chemistry, Cornell University Press, London, 1996, pp. 1153–1157.

    Google Scholar 

  11. Kano, K., S. Arimoto, and T. Ishimura, Conformational Enantiomerism of Bilirubin and Pamoic Acid Induced by Protonated Aminocyclodextrins, J. Chem. Soc., Perkin Trans. 2:1661–1666 (1995).

    Google Scholar 

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Koide, M., Ukawa, J., Tagaki, W. et al. Hydrolysis of nonionic ester surfactants facilitated by potassium β-glycyrrhizinate: Implication of catalytic functions played by the carboxyl groups. J Amer Oil Chem Soc 74, 49–54 (1997). https://doi.org/10.1007/s11746-997-0118-9

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  • DOI: https://doi.org/10.1007/s11746-997-0118-9

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