Hydration and dehydration behavior of aspartame hemihydrate

Journal of Pharmaceutical Sciences
S S LeungD J Grant

Abstract

Previous studies have shown that aspartame in the solid state can exist as a hemihydrate which occurs in two different polymorphic forms (I and II). The present work shows that equilibration of either hemihydrate at 25 degrees C with water vapor at relative humidities > or = 58% or with liquid water produces a 2.5-hydrate. Upon subjecting each of these crystalline hydrates to increasing temperature, the same crystalline anhydrate is formed which thermally cyclizes at a higher temperature to form the known compound 3-(carboxymethyl)-6-benzyl-2,5-dioxopiperazine. The activation energy of the cyclization reaction appears to depend on the degree of crystallinity of the anhydrate that is formed at a lower temperature. On increasing the temperature of the 2.5-hydrate, a hemihydrate intervenes before the anhydrate is formed. This intervening hemihydrate is similar to the commercial form (II) of aspartame hemihydrate but exhibits greater amorphous character. The techniques employed were Karl Fischer titrimetry, powder X-ray diffractometry, differential scanning calorimetry, thermogravimetric analysis, solid-state 13C nuclear magnetic resonance spectroscopy, and Fourier transform infrared absorption spectroscopy.

References

Jan 1, 1997·Journal of Pharmaceutical Sciences·S S Leung, D J Grant
Apr 21, 1998·Journal of Pharmaceutical Sciences·S S LeungD J Grant
Aug 1, 1963·Journal of Pharmaceutical Sciences·E SHEFTER, T HIGUCHI

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Citations

Nov 5, 1999·International Journal of Pharmaceutics·M E Brown, B D Glass
Apr 21, 1998·Journal of Pharmaceutical Sciences·S S LeungD J Grant
Apr 25, 2007·Journal of Pharmaceutical Sciences·Magali B HickeyOrn Almarsson
Mar 29, 2002·Journal of Pharmaceutical Sciences·Gregory T LongCharles A Wight
Jul 13, 2002·Journal of Pharmaceutical Sciences·Zedong DongDavid J W Grant
Apr 26, 2014·Critical Reviews in Food Science and Nutrition·Shan-Yang Lin, Chih-Cheng Lin
Feb 24, 2006·The Analyst·Robin K Harris
Jul 28, 2009·Pharmaceutical Development and Technology·Agris BērziņsJuris P Kreismanis
Jul 6, 2000·Analytical Chemistry·D Dollimore, P Phang

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