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479-13-0

479-13-0 Structure

479-13-0 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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 InformationBack 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. 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
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

COUMESTROL(479-13-0)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

479-13-0(sigmaaldrich)
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