2-METHOXYESTRADIOL

Base Information

• Chemical Name: 2-METHOXYESTRADIOL
• CAS No.: 362-07-2
• Molecular Formula: C19H26O3
• Molecular Weight: 302.414
• European Community (EC) Number: 636-846-8
• UNII: 6I2QW73SR5
• DSSTox Substance ID: DTXSID3040938
• Nikkaji Number: J104.105C
• Wikipedia: 2-Methoxyestradiol
• Wikidata: Q4596897
• NCI Thesaurus Code: C965
• Pharos Ligand ID: 24THBSMPKXVQ
• Metabolomics Workbench ID: 35293
• ChEMBL ID: CHEMBL299613
• Mol file: 362-07-2.mol

Synonyms:Estra-1,3,5(10)-triene-3,17b-diol, 2-methoxy- (7CI,8CI);Estradiol, 2-methoxy- (6CI);2-Hydroxyestradiol 2-methyl ether;2-Methoxyestra-1,3,5(10)-triene-3,17b-diol;NSC 659853;Panzem;

Chemical Property of 2-METHOXYESTRADIOL

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 2E-09mmHg at 25°C
• Melting Point: 188-190 °C
• Refractive Index: 1.586
• Boiling Point: 464.4 °C at 760 mmHg
• PKA: 10.29±0.60(Predicted)
• Flash Point: 234.7 °C
• PSA: 49.69000
• Density: 1.178 g/cm³
• LogP: 3.61780
• Storage Temp.: −20°C
• Solubility.: DMSO: 10 mg/mL
• 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:

99%, ^*data from raw suppliers

2-Methoxyestradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi,N
• Statements: 23/24/25-36/37/38-48-61-60-46-45-51/53
• Safety Statements: 22-26-36/37/39-45-53-36-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)OC)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)OC)O
• Recent ClinicalTrials: 2-Methoxyestradiol in Treating Patients With Advanced Solid Tumors
• Uses: A natural metabolite of 17?Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule a A natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly 2-Methoxyestradiol is a tubulin polymerization inhibitor and also decreases HIF-1 activity. 2-Methoxyestradiol depolymerizes microtubules and blocks HIF-1α nuclear accumulation and HIF-transcriptional activity. Phase 2. 2-Methoxy 17β-Estradiol is a natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. 2-Methoxy 17β-Estradiol binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly and function.

Technology Process of 2-METHOXYESTRADIOL

There total 4 articles about 2-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: 50.0%

2-bromoestradiol (15833-07-5) + sodium methylate (124-41-4) → estradiol (50-28-2) + 2-Methoxyestradiol (362-07-2)

Guidance literature:

With copper(l) iodide; In methanol; N,N-dimethyl-formamide;

Reference yield: 3.0%

2-Iodoestradiol (24381-12-2) → estradiol (50-28-2) + 2-Methoxyestradiol (362-07-2)

Guidance literature:

With copper(l) iodide; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/c39830000533

Reference yield: 3.0%

2-bromoestradiol (15833-07-5) → estradiol (50-28-2) + 2-Methoxyestradiol (362-07-2)

Guidance literature:

With copper(l) iodide; sodium methylate; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

diazomethane

2-Hydroxyestradiol

2-Iodoestradiol

2-bromoestradiol

Downstream raw materials:

2-methoxyestrone

2-Hydroxyestradiol

17beta-Estradiol 2,3-dimethyl ether

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

Refernces

• 1、 Teranishi,Fujii,Yamazaki,Miyabo. "Methylation of catechol estrogen with diazomethane". . p. 3309 - 3314. Retrieved 2007/10/02.