16alpha-Hydroxyestrone

Base Information

• Chemical Name: 16alpha-Hydroxyestrone
• CAS No.: 566-76-7
• Molecular Formula: C18H22O3
• Molecular Weight: 286.371
• European Community (EC) Number: 637-216-5
• UNII: JY611949JU
• DSSTox Substance ID: DTXSID901047947
• Nikkaji Number: J130.683I
• Wikipedia: 16%CE%B1-Hydroxyestrone
• Wikidata: Q27067422
• NCI Thesaurus Code: C120468
• Metabolomics Workbench ID: 35299
• ChEMBL ID: CHEMBL1233720
• Mol file: 566-76-7.mol

Synonyms:16 alpha-hydroxyestrone;16 beta-hydroxyestrone;16-alpha-hydroxyestrone;16-hydroxyestrone

Chemical Property of 16alpha-Hydroxyestrone

Chemical Property:

• Vapor Pressure: 1.53E-10mmHg at 25°C
• Melting Point: 209-211°C
• Refractive Index: 1.611
• Boiling Point: 493.2 °C at 760 mmHg
• PKA: 10.23±0.60(Predicted)
• Flash Point: 266.2 °C
• PSA: 57.53000
• Density: 1.195g/cm³
• LogP: 2.78820
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 286.15689456
• Heavy Atom Count: 21
• Complexity: 448

Purity/Quality:

98%Min ^*data from raw suppliers

16α-HydroxyEstrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2=O)O)CCC4=C3C=CC(=C4)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
• 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.
• Uses: 16α-Hydroxy Estrone (Estriol EP Impurity H) is a major metabolite of Estradiol.

Technology Process of 16alpha-Hydroxyestrone

There total 6 articles about 16alpha-Hydroxyestrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Estrone (53-16-7) → 4-hydroxyestrone (3131-23-5) + 2-hydroxyestrone (362-06-1,4735-38-0) + 16α-hydroxyestrone (566-76-7)

Guidance literature:

With cytochrome P₄₅₀ 1A₂; NADPH-generating system; In phosphate buffer; at 37 ℃; for 0.25h; pH=7.4; Further Variations:; Reagents; time; Enzyme kinetics;

DOI:10.1021/tx970217f

Reference yield:

oestrone acetate (901-93-9,21610-87-7,34990-86-8,57605-53-5,57605-54-6,57605-55-7) → 16α-Hydroxy-oestron (566-76-7,966-06-3,18186-49-7,80225-93-0) + 16α-bromoestrone (1228-71-3,71765-95-2,95340-34-4) + 16β-bromoestrone (1228-71-3,71765-95-2,95340-34-4)

Guidance literature:

With hydrogen bromide; bromine; potassium carbonate; Yield given. Multistep reaction; 1) CHCl₃, CH₃COOH, room temp., 20 min; 2) water, room. temp., 12 h.;

DOI:10.1007/BF00575701

Reference yield:

→ 16α-Hydroxy-oestron (566-76-7,966-06-3,18186-49-7,80225-93-0)

Guidance literature:

16-Oxo-oestron, Cytoplasmafraktion aus Rattenleber, NADH;

upstream raw materials:

oestrone acetate

Estrone

17-(2-methoxyethylimino)estra-1,3,5(10)-triene-3,16α-diol

Downstream raw materials:

3,16α-divaleryloxy-1,3,5(10)-estratrien-17-one

Estriol

Estrone

3-Hydroxyestra-1,3,5⁽¹⁰⁾-trien-16-one

Refernces

• 1、 Yamazaki, Hiroshi,Shaw, Peter M.,Guengerich, F. Peter,Shimada, Tsutomu. "Roles of cytochromes P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes". . p. 659 - 665. Retrieved 2007/10/03.
• 2、 Fedorova, O. I.,Morozova, L. S.,Alekseeva, L. M.,Grinenko, G. S.. "PREPARATION OF 16-SUBSTITUTED 3-HYDROXYESTRA-1,3,5(10)-TRIENE-17-ONE STARTING WITH THE BROMINATION OF ESTRONE ACETATE". . p. 437 - 440. Retrieved 2007/10/02.