Stability of Sucrose Fatty Acid Esters under Acidic and Basic Conditions

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  • Okumura Haruo
    Research & Development Division, Dai-ichi Kogyo Seiyaku Co., Ltd.
  • Kitazawa Naoki
    Research & Development Division, Dai-ichi Kogyo Seiyaku Co., Ltd.
  • Wada Shoichi
    Research & Development Division, Dai-ichi Kogyo Seiyaku Co., Ltd.
  • Hotta Hiroshi
    Research & Development Division, Dai-ichi Kogyo Seiyaku Co., Ltd.

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The stability of sucrose fatty acid monoesters toward hydrolysis under acidic and basic conditions was evaluated. Mass spectrometric analysis of hydrolysates showed that the glycosidic bond was preferentially hydrolyzed under acidic conditions, whereas the ester bond was selectively hydrolyzed under basic conditions. Under both conditions, the rate of hydrolysis depended on the pH of the solution, the concentration of sucrose monoesters, and the acylated position of the sucrose monoesters.<br>The hydrolysis of the glycosidic bond under acidic conditions was shown to be a first-order process. The rate constants for hydrolysis at various temperatures were measured, and the activation energies were calculated from the slope of the Arrhenius plots. The lifetime of sucrose monoesters estimated from the first-order rate constant for the hydrolysis reaction revealed that the sucrose monoesters have excellent long-term stability over a pH range of 5 to 7 at room temperature.

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