Add time:07/31/2019         Source:sciencedirect.com

1.1. We have confirmed the observation that incubation of 17β-hydroxyestr-4-en-3-one 1a with Botrodiplodia malorum yields almost exclusively the corresponding 1β-hydroxy compound.2.2. However, when estr-4-ene-3,17-dione 1b was incubated under the same conditions we found that the major product was 7β-hydroxyestr-4-ene-3,17-dione, obtained in 30–40% yield. Proof of structure and physical and chemical properties of this compound and the corresponding acetate are reported.3.3. Only a 3% yield of 1β-hydroxyestr-4-ene-3,17-dione was obtained.4.4. The other mono-oxygenated products isolated were 6β-hydroxyestr-4-ene-3,17-dione (10% yield) and estr-4-ene-3,11,17-trione (3% yield).5.5. Small amounts of many apparently poly-hydroxylated Δ4-3-ketones were also formed; one of these was tentatively identified as 7β,11β-dihydroxyestr -4-ene-3,17-dione.6.6. The transformations are discussed from the standpoint that an enzyme could mediate hydroxylation at more than one site.7.7. Syntheses of 6β-hydroxyestr-4-ene-3,17-dione, the corresponding 6β-acetate, estr-4-ene-3,6,17-trione, 17β-hydroxyestra-4,6-dien-3-one and estra-4,6-diene-3,17-dione are presented.

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