Add time:08/13/2019         Source:sciencedirect.com

After incubation of [7-3H]-16-dehydroprogesterone with the liver microsomal fraction of male Wistar rats, two radioactive metabolites were isolated and subsequently identified by gas liquid chromatography-mass spectrometry (g.l.c.-m.s.) as 16α,17-epoxy-3β-hydroxy-5α-pregnan-20-one and 16α,17-epoxy-progesterone. In addition to the epoxides, the following two Δ16-steroids were isolated: 3β-hydroxy-5α-pregn-16-en-20-one and 5α-pregn-16-ene-3,20-dione.The 16α,17-epoxides of C21-steroids are relatively stable compounds in contrast to the 16α,17α-epoxides of C18- and C19-steroids which are rapidly hydrolysed to trans-glycols in the presence of microsomes. Thus, after 30 min of incubation with rat liver microsomes, only 5% of tritiated 16α,17-epoxyprogesterone was metabolised; evidence was obtained that the reaction product was identical with 16β-hydroxyprogesterone, indicating that in the series of C21-steroids a reduction of the epoxide group takes place rather than a hydrolysis.

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