566-76-7

Basic information

• Product Name: 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE
• Synonyms: 16ALPHA-HYDROXYESTERONE;16ALPHA-HYDROXYESTRONE;1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE;1,3,5(10)-ESTRATRIEN-3,16-ALPHA-DIOL-17-ONE;3,16ALPHA-DIHYDROXY-1,3,5[10]-ESTRATRIEN-17-ONE;16A-hydroxyestrone;(16a)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one;3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one
• CAS NO: 566-76-7
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.37
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 566-76-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 209-211°C
• Boiling Point: 493.2 °C at 760 mmHg
• Flash Point: 266.2 °C
• Appearance: /
• Density: 1.195g/cm³
• Vapor Pressure: 1.53E-10mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 10.23±0.60(Predicted)
• CAS DataBase Reference: 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE(566-76-7)
• EPA Substance Registry System: 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE(566-76-7)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 566-76-7(Hazardous Substances Data)

Usage

Description

The naturally-occurring estrogens are estrone (E1, ), estradiol (E2, ), and estriol (E3, ). 16α-hydroxy Estrone (16α-OHE1) is a hydroxylated metabolite of E1 as well as an interconversion product with E2. E1 is 16α-hydroxylated by cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A5, CYP3A4, and CYP3A7, with CYP3A5 being breast-specific. 16α-OHE1 is sulphatized or glucuronidated before excretion. It is increased in rheumatoid arthritis and decreased by physical activity. Unlike the parent estrogens and other hydroxylated metabolites of E1, 16α-OHE1 binds covalently and persistently activates estrogen receptors. In addition, this metabolite increases cell proliferation and does not suppress TNF-α secretion, whereas other estrogen metabolites are not pro-proliferative and have marked effects on TNF-α secretion. The levels of 16α-OHE1 are increased in some forms of hormone therapy. Because hormone therapy increases breast cancer risk, 16α-OHE1 has been implicated as a risk factor for breast cancer, although supportive data remains elusive.

Chemical Properties

Pale Pink Solid

Uses

16α-Hydroxy Estrone (Estriol EP Impurity H) is a major metabolite of Estradiol.

Definition

ChEBI: The 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite.

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

Upstream product

• 137437-73-1 17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol 
• 53-16-7 Estrone 
• 901-93-9 oestrone acetate 

Downstream Products

• 30519-83-6 Trifluoro-acetic acid (8R,9S,13S,14S,16R)-13-methyl-17-oxo-3-(2,2,2-trifluoro-acetoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl ester 
• 105449-89-6 3,16α-divaleryloxy-1,3,5(10)-estratrien-17-one 
• 50-27-1 Estriol 
• 84693-92-5 16beta-Fluoroestradiol 
• 53-16-7 Estrone 
• 3601-97-6 3-Hydroxyestra-1,3,5⁽¹⁰⁾-trien-16-one 
• 6199-65-1 16-oxoestradiol 
• 1247-71-8 3,16α-diacetoxy-1,3,5(10)-estratrien-17-one 

Relevant articles and documents

Effect of metal ions on the stable adduct formation of 16α- hydroxyestrone with a primary amine via the Heyns rearrangement

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

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