16α-Hydroxyoestrone in the urine of pregnant women

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Abstract
16-Hydroxy-estrone diacetate, prepared from 16:17-epoxyestra-l:3:5-triene-3:17-dioldiacetate by the method of Leeds et al. (1954), yielded 16-hydroxy-estrone on cold acid hydrolysis. 16-Hydroxyestrone was also prepared directly from the epoxyacetate by cold acid treatment to 16-oxo-estradiol-17 in aqueous alkali at room temperature. The same rearrangement occurs when it is heated in vacuo to 220-230. A preparation of the ketonic-phenolic Kober chromogen (KC-5) prepared from enzymically-hydrolyzed late-pregnancy urine as described by Marrian et al. (1957) yielded a product after acetylation which was conclusively identified as 16 -hydroxyestrone diacetate. In view of the rearrangement undergone by 16 -hydroxyestrone in alkaline solution it is concluded that KC-5 as isolated from urine by the methods described consists of 16 -hydroxyestrone contaminated with about 20% of artifactually produced 16-oxo-estradiol-17. It is suggested that 16 -hydroxyestrone may be the metabolic intermediate between estrone and estriol.

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