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HomeProduct name listCOUMESTROL

COUMESTROL

Synonym(s):7,12-Dihydroxycoumestan

  • CAS NO.:479-13-0
  • Empirical Formula: C15H8O5
  • Molecular Weight: 268.22
  • MDL number: MFCD00016885
  • EINECS: 207-525-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:07:02
COUMESTROL Structural

What is COUMESTROL?

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

The Uses of COUMESTROL

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

The Uses of COUMESTROL

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.

What are the applications of Application

Coumestrol is a plant estrogen & highly potent inhibitor of 17-β-hydroxysteroid oxidoreductase

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.

Properties of COUMESTROL

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
CAS DataBase Reference 479-13-0(CAS DataBase Reference)
EPA Substance Registry System Coumestrol (479-13-0)

Safety information for COUMESTROL

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for COUMESTROL

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