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The possibility that certain types of urinary steroid conjugates might be selectively hydrolysed by boiling the urine at a neutral pH was first suggested by the work of Speirs, Wragg, Bonner & Homburger (1951), in which it was shown that chloroformextractable material, active in the mouse-eosinophil test of Speirs & Meyer (1951), could be liberated in urines by this method from patients treated with adrenocorticotrophic hormone. Further attention was drawn to this possibility by the demonstration of Teich, Rogers, Lieberman, Engel & Davies (1953) that sodium dehydroepiandrosterone (3f,-hydroxy

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Watson & Marrian (1955) detected the presence in extracts of the urine of pregnant women of a ketonic Kober chromogen which was more 'polar' than oestrone, and, on solvent-partition evidence, concluded that it was 16-oxo-oestradiol-17P (16-oxo-oestra-1:3:5-triene-3:17,B-diol). More recently Marrian, Watson & Panattoni (1957) concentrated this Kober chromogen (KC-5) and showed conclusively that the major component in it must have been either 16m-hydroxyoestrone (17-oxo-oestra-1:3:5-triene-3:160-diol) or 16p-hydroxyoestrone (17-oxo-oestra-1 :3:5-triene-3: 16,B-diol), and not 16-oxo-oestradiol-17,. On biogenetic grounds the view was favoured that the major component in KC-5 was 16m-hydroxyoestrone rather than 16phydroxyoestrone, but since reduction with sodium borohydride yielded a mixture of oestriol (oestra-