On the Hot Acid Hydrolysis of 5α-Pregnane-3α, 20α-diol Disulfate

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Treatment of 5α-pregnane-3α, 20-αdiol disulfate (II) with 3 N hydrochloric acid under heating gave a corresponding hydrolyzate, which was shown to contain various degradation products by gas chromatography. The structural assignment of these materials was investigated by gas chromatography-mass spectrometry and these were identified as: 17α-ethyl-17β-methyl-5α-androst-13-en-3α-ol (III), two isomeric compounds (IV and V) of 5α-pregn-17 (20)-en-3 α-ol, and 5α-pregnane-3α, 20β-diol (VI). The yield of the intact aglycone (I) obtained was less than 20% of the total steroid produced.<BR>The speculation of the structures on other minor products is also described and the mechanism on the formation of degradation products is briefly discussed.
Japan Society of Clinical Chemistryの論文