Estrogenic Dihydroxy Compounds in the Urine of Pregnant Mares

Abstract

Schwenk and Hildebrandt 1 described the isolation from the urine of pregnant mares of a new compound of high estrogenic potency. This substance, designated by them δ- follicular hormone, melted at 209°, gave a characteristic purple color when coupled with p-nitro-diazobenzene and showed a gold yellow fluorescence in concentrated sulfuric acid solution. Analysis of the compound itself and of its mono-benzoate indicated the composition C₁₈H₂₂O₂. Treatment with ketone reagents failed to give characteristic derivatives.

Another batch of pregnant mare's urine has now been worked up in the laboratories of the Schering Corporation (Bloomfield, N. J.). The compound present in largest amount in the crude fraction containing the phenol-alcohols is the above δ-follicular hormone. Analysis of the present preparation gave figures agreeing better with C₁₈H₂₄O₂ than with C₁₈H₂₂O₂. The preparation of a di-p-nitro-benzoate (m.p. 260° uncorr.) leaves no doubt that both oxygen atoms are present in the form of hydroxyl groups.

A second substance isolated is apparently identical with the lower melting member (m.p. 174° uncorr.) of the pair of isomeric hy-droxyphenols (“α-dihydrofollicular hormone”) which Schwenk and Hildebrandt 2 obtained by reduction of theelin. It shows the same characteristic blue fluorescence in sulfuric acid solution as the dihy-drofollicular hormone and gives no depression of melting point when mixed with the latter. Furthermore, a small amount of a compound melting at 236° (uncorr.) which is more difficultly soluble in absolute methyl alcohol than the δ-hormone could be separated from the top fractions of the latter. The amount of the 2 last-named substances isolated was not sufficient for analysis and the preparation of derivatives.