COUMESTROL

Base Information

• Chemical Name: COUMESTROL
• CAS No.: 479-13-0
• Molecular Formula: C15H8 O5
• Molecular Weight: 268.226
• Mol file: 479-13-0.mol

Synonyms:3-Benzofurancarboxylicacid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, d-lactone (6CI); 2-(2,4-Dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylicacid d-lactone;3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one; Coumesterol; Coumestrol;Cumoestrol; Cumostrol; NSC 22842

Chemical Property of COUMESTROL

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 3.58E-07mmHg at 25°C
• Melting Point: ≥350 °C(lit.)
• Refractive Index: 1.7680 (estimate)
• Boiling Point: 406 °C at 760 mmHg
• PKA: 8.25±0.20(Predicted)
• Flash Point: 199.3 °C
• PSA: 83.81000
• Density: 1.602 g/cm³
• LogP: 3.10360
• Storage Temp.: Refrigerator
• Solubility.: DMSO: soluble

Purity/Quality:

≥98% ^*data from raw suppliers

Coumestrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol, ) binds the estrogen receptors ERα (IC50 = 11 nM) and ERβ (IC50 = 2 nM) and can induce ER-dependent gene expression in isolated cells. Coumestrol is also a weak antagonist of pregnane X receptor (IC50 = 12 μM) as well as a potential inverse agonist of the constitutive androstane receptor (EC50 = 30 μM).
• Uses: This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

Technology Process of COUMESTROL

There total 72 articles about COUMESTROL 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: 99.0%

toluene-4-sulfonic acid 3-hydroxy-6-oxo-6H-benzo[4,5]furo[3,2-c]chromen-9-yl ester (870456-46-5) → coumestrol (479-13-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1021/jo0517038

Reference yield: 97.0%

coumestrol (796089-78-6) → coumestrol (479-13-0)

Guidance literature:

In ethanol; for 3h; Reflux;

Reference yield: 96.0%

Coumestrol dimethyl ether (3172-99-4) → coumestrol (479-13-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 17h; Inert atmosphere; Cooling with ice;

upstream raw materials:

3-(2,4-dimethoxy-phenyl)-4,7-dihydroxy-coumarin

3-(2,4-dimethoxyphenyl)-4-hydroxy-7-methoxy-1-benzopyran-2-one

2,3-bis-(2,4-dimethoxy-phenyl)-3-oxo-propionitrile

Coumestrol dimethyl ether

Downstream raw materials:

2-(2,4-dimethoxy-phenyl)-6-methoxy-benzofuran-3-carboxylic acid methyl ester

Coumestrol dimethyl ether

3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-phenoxy-6H-benzo[4,5]furo[3,2-c]chromene

Refernces

• 1、 Cao, Tongxiang,Jiang, Huanfeng,Zhang, Ling,Zhu, Shifa. "Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran". . p. 4670 - 4677. Retrieved 2020/02/20.
• 2、 -. "Method for preparing coumarino-heteroaromatic ring compounds and derivatives thereof through intramolecular cross-dehydrogenation coupling". Paragraph 0230; 0231; 0232. . Retrieved 2018/04/01.