Synthesis of diethylstilbestrol metabolites : ω-hydroxy-DIENESTROL (cas 13029-44-2) and derivatives

Add time:09/09/2019    Source:sciencedirect.com

ω-Hydroxy-β-dienestrol and some of its derivatives have been synthesized from α-dienestroldiacelate via the ω-bromo- and ω-acetoxy-β-dienestroldiacetate. The NMR and mass spectra of these compounds and their stereochemistry are discussed. Thin layer chromatography, gas chromatography and mass spectrometry show that synthetic ω-hydroxy-β-dienestrol is identical with a major metabolite of diethylstilbestrol. The identity is further substantiated by reverse isotope dilution analysis of the acetylated metabolite. ω-Acetoxy-β-dienestroldiacetate is shown to have alkylating potential in the 4-(p-nitrobenzyl)pyridine test.

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