| Identification | More | [Name]
COUMESTROL | [CAS]
479-13-0 | [Synonyms]
[2-(2,4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURAN-CARBOXYLIC ACID ALPHA-LACTONE]
2-(2,4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCARBOXYLIC ACID DELTA-LACTONE
2-(2 4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCARBOXYLIC ACID D-LACTONE
3,9-DIHYDROXY-6H-BENZOFURO[3,2-C]-[1]BENZOPYRAN-6-ONE
7,12-DIHYDROXYCOUMESTAN
7,12-DIHYDROXYCOUMESTANE
7(1), 6-DIHYDROXYCOUMARINO(3(1), 4(1), 3,2)COUMARONE
COUMESTROL
2-(2,4-dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylicacidelta-lacton
2-c)(1)benzopyran-6-one,3,9-dihydroxy-6h-benzofuro(
2-c][1]benzopyran-6-one,3,9-dihydroxy-6h-benzofuro[
cumoesterol
Coumesterol
COUMESTROL(P)
COUMOESTROL
7 12-DIHYDROXYCOUMESTAN 98%
2-(2 4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCARBOXYLIC ACID D-LACTONE 98% | [EINECS(EC#)]
207-525-6 | [Molecular Formula]
C15H8O5 | [MDL Number]
MFCD00016885 | [Molecular Weight]
268.22 | [MOL File]
479-13-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow to Beige Powder | [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 | [Usage]
This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution | [BRN ]
266702 | [LogP]
2.940 (est) | [CAS DataBase Reference]
479-13-0(CAS DataBase Reference) | [EPA Substance Registry System]
Coumestrol (479-13-0) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
DF8077000
| [F ]
10 | [Safety Profile]
An experimental
teratogen. Other experimental reproductive
effects. Mutation data reported. When
heated to decomposition it emits acrid
smoke and irritating fumes. |
| Hazard Information | Back Directory | [Description]
Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol, Item No. 10006315) binds the estrogen receptors ERα (IC50 = 11 nM) and ERβ (IC50 = 2 nM) and can induce ER-dependent gene expression in isolated cells.1,2 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).3 | [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 | [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. | [storage]
Store at -20°C | [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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