The isolation of 6-α-hydroxyoestrone from the urine of pregnant women

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Abstract
In view of previous experiments in vitro in vivo in which 6-hydroxylation of phenolic steroids by various tissues was demonstrated an attempt was made to isolate 6-hydroxy estrogens from the urine of pregnant women. During this work it was found that free 6[alpha]- as well as 6[beta]-hydroxylated estrogens were extremely unstable under acidic conditions (pH<3); it was therefore necessary to establish experimental conditions under which no rearrangement of the hydroxyl group would take place. By avoiding acid steps during the experimental procedures a ketonic-phenolic fraction was obtained from enzymically hydrolysed late-pregnancy urine that was subjected to paper chromatography in various systems. By using similar methods on a large scale partition chromatography on Celite columns a crystalline material was obtained from 1001 of late-pregnancy urine that was identified as 6[alpha]-hydroxyestrone by various chemical reactions by infrared spectroscopy.