It was reported previously (Meyer et al., 1955 a, Meyer, 1955 a) that incubation of dehydroepiandrosterone (I) and Δ4-androstene-3,17-dione (II) with bovine adrenal homogenate preparations produced a wide galaxy of conversion products. Of these, 11β-hydroxyandrostenedione (IV), 6β-hydroxyandrostenedione (V), 19-hydroxyandrostenedione (VI), and Δ4-androstene-3,11,17-trione (III) were isolated in crystalline form and identified. The presence of 6α-hydroxyandrostenedione (VII) and Δ4-androstene-3,6,17-trione (IX) was indicated by their mobilities in paper chromatographic systems and by spectroscopic data. For compound VIII, Rtol. 0.25 cm./h., the structure 6α, 1 1β-dihydroxyandrostenedione was tentatively postulated (as will be seen, erroneously) on the grounds of the rate of formation of a colour product in alkaline ethanolic solution and the infrared spectra of the compound and its acetate (VIII a).
A more definite proof of the structure of compound VIII was desirable. It could be anticipated that incubation of 6α-hydroxyandrostenedione (VII) with adrenal tissue would