Synthesis of 1,3,5(10)-Estratriene-3,16β,17α-triol<sup>1</sup>

Fishman, Jack; Biggerstaff, Warren R.

doi:10.1021/jo01102a028

Cited by 23 publications

(3 citation statements)

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“…For the 11-bromo-12-ketosteroid listed, the more stable 11aepimer (3) reduces at a slightly higher negative potential. The 16a-and 16/3bromo -3 -hydroxyestra -1,3,5(10)trien-17-ones reduce in the same order of thermodynamic stability (7) as the previously mentioned epimers. Wilson and Allinger ( 16) have reached this conclusion from an independent study carried out with simple 2-halocyclohexanones.…”

Section: Resultssupporting

confidence: 52%

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Kabasakalian¹,

McGlotten²

1962

Anal. Chem.

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Section: Resultssupporting

confidence: 52%

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Kabasakalian¹,

McGlotten²

1962

Anal. Chem.

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“…For the 11-bromo-12-ketosteroid listed, the more stable 11aepimer (3) reduces at a slightly higher negative potential. The 16a-and 16/3bromo -3 -hydroxyestra -1,3,5 (10)trien-17-ones reduce in the same order of thermodynamic stability (7) as the previously mentioned epimers. Wilson and Allinger (16) have reached this conclusion from an independent study carried out with simple 2-halocyclohexanones.…”

supporting

confidence: 56%

Correction- Time-of-Flight Mass Spectrometry: Application to Capillary Column Gas Chromatography

Gohlke¹

1962

Anal. Chem.

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“…16ß,17ß-epoxy-oestratrienol acetate (16ß,17ß-epoxy-l,3,5(10)-oestratrien-3-ol acetate) was synthesised according to the method of Fishman & Biggerstaff (1958). [6,7-3H2]oestratetraenol ([6,7-%]°°l ,3,5(10),16-oestratetraen-3-ol, 6.26 Ci/mol) and [6,7-3H2]epoxy-oestratrienol acetate ([6,7-3H2]16a, 17a-epoxyl,3,5(10)-oestratrien-3-ol acetate, 6.25 Ci/mol) were pre¬ pared by chemical synthesis from [6,7-3H2]oestradiol-17ß ([6,7-3H2]l,3,5(10)-oestratriene-3,17ß-diol, 48 Ci/mmol, New England Nuclear, Boston, USA), which was diluted with non-labelled oestradiol-17ß to a final specific radio¬ activity of 6.25 Ci/mol.…”

Section: Steroidsmentioning

confidence: 99%

Biosynthesis of 16α,17α-epoxy-oestratrienol in rat liver microsomes

Siekmann¹,

Thull²,

Breuer³

1980

Acta Endocrinologica

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After incubation of 1,3,5(10),16-oestratetraenol, a 16-dehydrosteroid, with rat liver microsomes, 16\g=a\, 17\g=a\-epoxy-oestratrienol was isolated as metabolite. The compound was detected by the use of mass fragmentography after purification of the incubation extract by thin-layer chromatography. Since the epoxide is rapidly hydrolysed by a hepatic epoxide hydratase, only very small concentrations of this metabolite were present in the incubation extract. When styrene oxide was added to the incubation mixture as inhibitor of the epoxide hydratase, the yield of the steroid epoxide increased considerably. Final identification of the oestrogen epoxide was performed by recording mass spectra and by comparison with authentic reference material.Previous studies of the metabolism of oestrogens have shown that the 16-dehydrosteroid 1,3,5(10)-16-oestratetraen-3-ol is transformed in vivo and in vitro (Breuer & Knuppen 1961; Breuer 1962) to the transglycol 16,17-i?/tt-oestrioI (l,3,5(10)-oestratrien-3,16ß,17a-triol); these inve¬ stigations suggested that a 16a,17a-epoxide may be formed as an intermediate in the course of the biosynthesis of 16,17-i?p¿-oestriol. It is well known that epoxides of polycyclic hydrocarbons are highly active carcinogens (Sims & Grover 1974). There¬ fore, it appears of great interest to find out if compounds with an epoxide structure are formed in the metabolism of steroids. However, so far attempts to isolate and to identify 16a,17a-epoxyl,3,5(10)-oestratrien-3-ol as a metabolic product failed. This may have been due to the fact that, as a result of the effective epoxide hydratase (Bindel et al. 1979), only very small concentrations of the epoxide were present in the incubation mixtures.In the present paper, the isolation and identifica¬ tion of 16a, 17a-epoxy-l,3,5(10)-oestratrien-3-ol, formed during incubations of 1,3,5(10),16-oestratetraen-3-ol with rat liver microsomes, is described.Evidence for the presence of low amounts of the biologically labile epoxide was obtained by using the highly sensitive technique of mass fragmentography. Final identification of the oestrogen epox¬ ide was performed by recording mass spectra. Materials and Methods SteroidsOestrone (3-hydroxy-l,3,5(10)-oestratrien-17-one), oestradiol-17ß (l,3,5(10)-oestratriene-3,17ß-diol) and oe¬ striol (l,3,5(10)-oestratriene-3,16a,17ß-triol) were pur¬ chased from Schering, Berlin; 16,17-^¿-oestriol (1,3,5-(10)-oestratriene-3,16ß,17a-triol), 16-

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Synthesis of 1,3,5(10)-Estratriene-3,16β,17α-triol¹

Cited by 23 publications

References 0 publications

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Correction- Time-of-Flight Mass Spectrometry: Application to Capillary Column Gas Chromatography

Biosynthesis of 16α,17α-epoxy-oestratrienol in rat liver microsomes

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Synthesis of 1,3,5(10)-Estratriene-3,16β,17α-triol1

Cited by 23 publications

References 0 publications

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Polarographic Reduction of Epimeric α-Haloketosteroids and Their Vinylogs.

Correction- Time-of-Flight Mass Spectrometry: Application to Capillary Column Gas Chromatography

Biosynthesis of 16α,17α-epoxy-oestratrienol in rat liver microsomes

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Synthesis of 1,3,5(10)-Estratriene-3,16β,17α-triol¹