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| | COUMESTROL Basic information |
| | 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 | | pka | 8.25±0.20(Predicted) | | form | Light beige solid. | | 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) |
| | 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. |
| | COUMESTROL Preparation Products And Raw materials |
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