3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-on

Bezeichnung:3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-on

CAS-Nr479-13-0

Englisch Name:COUMESTROL

CBNumberCB2339816

SummenformelC15H8O5

Molgewicht268.22

MOL-Datei479-13-0.mol

Synonyma

3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-on

3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	≥350 °C(lit.)
Siedepunkt	331.39°C (rough estimate)
Dichte	1.2586 (rough estimate)
Brechungsindex	1.7680 (estimate)
storage temp.	Refrigerator
Löslichkeit	DMSO: soluble
Aggregatzustand	Light beige solid.
pka	8.25±0.20(Predicted)
Farbe	Pale Yellow to Dark Brown
BRN	266702
LogP	2.940 (est)
CAS Datenbank	479-13-0(CAS DataBase Reference)
EPA chemische Informationen	Coumestrol (479-13-0)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	DF8077000
F	10

Gefahreninformationscode (GHS)

COUMESTROL Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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).
Chemische Eigenschaften
Yellow to Beige Powder
Verwenden
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.
Sicherheitsprofil
An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Einzelnachweise
[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.

3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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