2-Hydroxyestrone

Base Information

• Chemical Name: 2-Hydroxyestrone
• CAS No.: 362-06-1
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.371
• European Community (EC) Number: 636-847-3
• UNII: UQS3A06ILY
• DSSTox Substance ID: DTXSID80904315
• Nikkaji Number: J108.087C
• Wikipedia: 2-Hydroxyestrone
• Wikidata: Q27105413
• NCI Thesaurus Code: C63947
• Metabolomics Workbench ID: 35291
• ChEMBL ID: CHEMBL1627343
• Mol file: 362-06-1.mol

Synonyms:2-hydroxyestrone;2-hydroxyestrone, 4-(14)C-labeled

Chemical Property of 2-Hydroxyestrone

Chemical Property:

• Vapor Pressure: 6.87E-10mmHg at 25°C
• Melting Point: 199-201°C
• Boiling Point: 481.3°C at 760 mmHg
• PKA: 10.10±0.40(Predicted)
• Flash Point: 259°C
• PSA: 57.53000
• Density: 1.241g/cm³
• LogP: 3.52300
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• 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

2-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(C1CCC2=O)CCC4=CC(=C(C=C34)O)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=C(C=C34)O)O
• Uses: A metabolite of Estradiol A metabolite of Estradiol.

Technology Process of 2-Hydroxyestrone

There total 29 articles about 2-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: 93.1%

2-acetyl-3-hydroxyestra-1,3,5(10)-trien-17-one (26357-02-8) → 2-hydroxyestrone (362-06-1,4735-38-0)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In diethylene glycol dimethyl ether; at 12 ℃; for 5h;

DOI:10.1016/0039-128X(82)90016-2

Reference yield: 88.0%

C26H40O3Si (1315577-32-2) → 2-hydroxyestrone (362-06-1,4735-38-0)

Guidance literature:

C₂₆H₄₀O₃Si; With palladium(II) trimethylacetate; [bis(acetoxy)iodo]benzene; In toluene; at 100 ℃; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

With water; In tetrahydrofuran;

DOI:10.1021/ja208572v

Reference yield: 47.0%

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

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; chloroform; at -25 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.03.060

upstream raw materials:

2-acetyl-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one

19-hydroxy-4β,5-epoxy-5β-androstane-3,17-dione

2-Aminoestrone

2-methoxyestrone

Downstream raw materials:

2-methoxy-3-acetoxyestra-1,3,5⁽¹⁰⁾-trien-17-one

2-hydroxyestradiol 2,3-dibenzoate

2,3-estrogen o-quinone

2,3-dibenzyloxy-1,3,5⁽¹⁰⁾-estratriene-17-one

Refernces

• 1、 Cheng, Qian,Sohl, Christal D.,Yoshimoto, Francis K.,Guengerich, F. Peter. "Oxidation of dihydrotestosterone by human cytochromes P450 19A1 and 3A4". . p. 29554 - 29567. Retrieved 2013/01/14.
• 2、 Pezzella, Alessandro,Lista, Liliana,Napolitano, Alessandra,D'Ischia, Marco. "An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation". . p. 3541 - 3544. Retrieved 2007/10/03.