Solvolyses of Polyhydric Alcohol Esters. I. Stability of meso-Inositol Hexanicotinate in Acidic Medium

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The quantitative procedure of nicotinic acid liberated from meso-inositol hexanicotinate (IHN) and several nicotinic acid esters of polyhydric alcohols and the stability in acidic solution were investigated to predict the gastric stability for a possible explanation of their absorption from the gastrointestinal tract. Nicotinic acid formed by the degradation could be satisfactorily separated from the other degraded products by the ion-exchange chromatography. The results were in agreement with those of the titrimetry. The thinlayer chromatography on the degradation of IHN showed that IHN was solvolyzed to many intermediates which then successively decomposed to further degraded products. The initial solvolytic rate of IHN in 0.1N HCl and at 37.0°was faster than about ten times those of the other nicotinic acid esters used. The observed rate of the degradation of IHN was first order with respect to IHN concentration at a constant temperature and hydrogen ion concentrations by the thin-layer chromatographic technique. The variation of the rate constant was minor in the range of 0.04 to 1.0N HCl and at 37.0°. The dissolution of IHN from tablets, the enzymatic stability and the solubility of IHN were also discussed.

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