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COUMESTROL

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COUMESTROL Basic information

Product Name:
COUMESTROL
Synonyms:
  • cumoesterol
  • COUMOESTROL
  • 7 12-DIHYDROXYCOUMESTAN 98%
  • Coumesterol
  • COUMESTROL(P)
  • Coumestrol, >98%
  • 3,9-dihydroxy-6-benzofuro[3,2-c][1]benzopyranone
  • 2-(2 4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCARBOXYLIC ACID D-LACTONE 98%
CAS:
479-13-0
MF:
C15H8O5
MW:
268.22
EINECS:
207-525-6
Product Categories:
  • Steroids & Hormones - 13C & 2H
  • Steroids
  • Coumarins
  • Iso-Flavones
Mol File:
479-13-0.mol
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COUMESTROL Chemical Properties

Melting point:
≥350 °C(lit.)
Boiling point:
331.39°C (rough estimate)
Density 
1.2586 (rough estimate)
refractive index 
1.7680 (estimate)
storage temp. 
Refrigerator
solubility 
DMSO: soluble
form 
Light beige solid.
pka
8.25±0.20(Predicted)
color 
Pale Yellow to Dark Brown
BRN 
266702
LogP
2.940 (est)
CAS DataBase Reference
479-13-0(CAS DataBase Reference)
EPA Substance Registry System
Coumestrol (479-13-0)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
DF8077000
10

MSDS

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COUMESTROL Usage And Synthesis

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).

Chemical Properties

Yellow to Beige Powder

Uses

This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

Definition

ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.

Synthesis Reference(s)

Tetrahedron Letters, 4, p. 1151, 1963 DOI: 10.1039/jr9630005127

Biochem/physiol Actions

Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

References

[1]. chen hy, dykstra kd, birzin et, et al. estrogen receptor ligands. part 1: the discovery of flavanoids with subtype selectivity. bioorg med chem lett. 2004 mar 22;14(6):1417-21.
[2]. hopert ac, beyer a, frank k, et al. characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. environ health perspect. 1998 sep;106(9):581-6.
[3]. wang h, li h, moore lb, et al. the phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane x receptor. mol endocrinol. 2008 apr;22(4):838-57.

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