2-hydroxypropyldigitonin: Synthesis and properties of preparations differing in degree of substitution

Abstract Reaction of propylene oxide with digitonin in strong aqueous alkali yielded water soluble, nontoxic solubilizers of drugs and hormones, the molecular composition of which could be fully deduced from plasma desorption mass spectrometry data. Preparations with average degrees of substitution ranging from 0.7 to 4.5 were investigated, and all the distributions of degrees of substitution observed were relatively narrow and symmetrical; thus, the reactivity of primary and secondary hydroxyls of saponin and of its conversion products had to be quite similar. The effects of the average degree of substitution of 2-hydroxypropyldigitonins on the formation of micelles and on the solubilization of four drugs into aqueous solutions were found to be minor. On the other hand, the ability to hemolyze erythrocytes decreased sharply with an increasing average degree of substitution.