Synthesis of Sexual Hormone Glycuronides

Abstract

THE importance of glycuronic acid lies in its property of condensing with hydroxylic compounds to produce the so-called coupled glycuronic acids. In this way these substances become soluble in water and therefore also in urine. From the researches of Cohen and Marrian1, Cohen, Marrian and Odell2, as well as those of Venning and Browne3, glycuronic acid also plays a part in the mechanism of the elimination of the sex hormones. These investigators succeeded in isolating and identifying œ“striol glycuronide in an amorphous form (Marrian), and pregnandiol glycuronide in a crystalline condition (Venning and Browne), from pregnancy urine. The crystalline sodium salt of œ”striol glycuronide proved to be about thirty times as weak as free œ“striol on a subcutaneous injection into adult ovariectomized mice. Pregnandiol glycuronide was claimed by Venning and Browne to be the form in which progesterone is eliminated. The latter cannot couple, however, and must first of all be converted into the hydroxylated pregnandiol, within the organism. I wish to report here the synthetic preparation of the coupled, glycuronic acids of dehydroandrosterone and of I±-œ”stradiol monobenzoate.