4-Methoxyestradiol

Base Information

• Chemical Name: 4-Methoxyestradiol
• CAS No.: 26788-23-8
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.414
• UNII: R6YV5Q2LKS
• DSSTox Substance ID: DTXSID50949596
• Nikkaji Number: J418.324J
• Wikipedia: 4-Methoxyestradiol
• Wikidata: Q28209791
• NCI Thesaurus Code: C120469
• Metabolomics Workbench ID: 42103
• ChEMBL ID: CHEMBL4084860
• Mol file: 26788-23-8.mol

Synonyms:4-methoxyestradiol;4-methoxyestradiol-17 beta

Chemical Property of 4-Methoxyestradiol

Chemical Property:

• Vapor Pressure: 1.03E-09mmHg at 25°C
• Boiling Point: 472°Cat760mmHg
• PKA: 10.29±0.60(Predicted)
• Flash Point: 239.2°C
• PSA: 49.69000
• Density: 1.178g/cm³
• LogP: 3.61780
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Sonicated), Methanol
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 302.18819469
• Heavy Atom Count: 22
• Complexity: 425

Purity/Quality:

97% ^*data from raw suppliers

4-Methoxy17β-Estradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4OC)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4OC)O
• Uses: A metabolite of 17?Estradiol A metabolite of 17β-Estradiol.

Technology Process of 4-Methoxyestradiol

There total 10 articles about 4-Methoxyestradiol 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: 96.0%

4-iodo-17β-estradiol (61748-87-6) + sodium methylate (124-41-4) → 4-methoxy-17β-estradiol (26788-23-8,104542-68-9)

Guidance literature:

With copper dichloride; In methanol; N,N-dimethyl-formamide; at 110 ℃; for 0.0833333h; Heating;

Reference yield: 80.0%

4-bromo-β-estradiol (1630-83-7) + sodium methylate (124-41-4) → 4-methoxy-17β-estradiol (26788-23-8,104542-68-9)

Guidance literature:

copper(l) iodide; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; In N,N-dimethyl-formamide; at 105 - 110 ℃; for 13h;

DOI:10.1016/0039-128X(86)90077-2

Reference yield:

2,4-dibromoestradiol (19590-55-7) → 4-methoxy-17β-estradiol (26788-23-8,104542-68-9)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Pd/C / ethanol / Ambient temperature

2: 40 percent / NBS / dimethylformamide / 24 h / Ambient temperature

3: 75 percent / CuCl₂ / methanol; dimethylformamide / 1.25 h / 110 °C / Heating

With N-Bromosuccinimide; hydrogen; copper dichloride; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

diazomethane

4-Hydroxyestradiol

4-bromo-β-estradiol

sodium methylate

Downstream raw materials:

3-benzyloxy-4-methoxyestra-1,3,5(10)-trien-17β-ol

potassium 3-benzyloxy-4-methoxyestra-1,3,5(10)-trien-17β-yl sulfate