566-76-7 Usage
Description
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE, also known as 16α-Hydroxy Estrone (Estriol EP Impurity H), is a minor estrogen metabolite derived from the naturally-occurring estrogens estrone (E1), estradiol (E2), and estriol (E3). It is a pale pink solid that is formed through the hydroxylation of E1 by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific. This metabolite is unique in its ability to bind covalently and persistently activate estrogen receptors, leading to increased cell proliferation and altered TNF-α secretion.
Uses
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE is used as a research compound for studying the effects of estrogen metabolism and its role in various physiological and pathological processes.
Used in Pharmaceutical Industry:
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE is used as a reference standard for the development and validation of analytical methods in the pharmaceutical industry, particularly in the synthesis and quality control of estrogen-related drugs.
Used in Medical Research:
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE is used as a biomarker in medical research to investigate its potential role as a risk factor for breast cancer and other hormone-related conditions. Its increased levels in some forms of hormone therapy and its unique properties make it a subject of interest for understanding the complex interactions between estrogen metabolism and cancer development.
Used in Endocrinology:
1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE is used in endocrinology to study the effects of estrogen metabolism on hormone levels, cell proliferation, and immune response, particularly in the context of rheumatoid arthritis and the influence of physical activity on estrogen metabolite levels.
Check Digit Verification of cas no
The CAS Registry Mumber 566-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 566-76:
(5*5)+(4*6)+(3*6)+(2*7)+(1*6)=87
87 % 10 = 7
So 566-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
566-76-7Relevant articles and documents
Effect of metal ions on the stable adduct formation of 16α- hydroxyestrone with a primary amine via the Heyns rearrangement
Miyairi, Shinichi,Maeda, Kaoru,Oe, Tomoyuki,Kato, Toyoaki,Naganuma, Akira
, p. 252 - 258 (2007/10/03)
16α-Hydroxyestrone (16α-OHE1), one of the major estrogen metabolites in humans that may plays a role in cell transformation, has been found to form stable adducts with nuclear proteins. The mechanism for the formation of a stable covalent adduct of 16α- OHE1 with protein has been postulated via the Heyns rearrangement after Schiff base formation. The Heyns rearrangement on the steroidal D-ring α-hydroxyimine was investigated using 17-(2- methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol as a model intermediate. Rates of the Heyns rearrangement and hydrolysis of the steroidal α- hydroxyimine were determined by a high-performance liquid chromatography (HPLC) simultaneously. The Heyns rearrangement was demonstrated to be optimum at pH 6.2 and the reaction rate at physiological pH, 7.3-7.5, was more than 90% of that at the optimum pH. On the other hand, modulator(s) to the reactions were also examined. According to our previous finding of the proton-mediated mechanism of the Heyns rearrangement, the effects of cationic metal ions on the reactions were examined with 29 metal chlorides. Five metal ions, Pt4+, Cu2+, Ni2+, Co2+, and Mn2+, suppressed the formation of Heyns product significantly while Fe2+, Y3+, Gd3+, and Er3+ slightly increased it. The suppression rate was synergistically enhanced by the combination of Pt4+ with Co2+, Cu2+, or Ni2+. These results suggest the five metal ions, Pt4+, Cu2+, Ni2+, Co2+, and Mn2+, reduce the formation of the Heyns product in vivo and, therefore, would be useful tools to clarify the implication of the stable adduct formation of 16α-OHE1 with protein.
Microbiologic oxidation of estratrienes and estratetraenes by Streptomyces roseochromogenes ATCC 13400
Ferrer,Calzada,Bonet
, p. 390 - 394 (2007/10/02)
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