3,3′-Methylene-bis(4-hydroxycoumarin)

Name: 3,3′-Methylene-bis(4-hydroxycoumarin)
Brand: SIGMA

Synonym(s):

Bishydroxycoumarin, Dicoumarol, Dicumarol

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₂O₆

CAS Number:

66-76-2

Molecular Weight:

336.29

NACRES:

NA.47

PubChem Substance ID:

24896643

UNSPSC Code:

12352103

EC Number:

200-632-9

MDL number:

MFCD00006857

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Properties

biological source

synthetic (organic)

Quality Segment

100

assay

≥98% (TLC)

form

powder

mp

290-292 °C (lit.)

solubility

pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow

SMILES string

OC1=C(CC2=C(O)c3ccccc3OC2=O)C(=O)Oc4ccccc14

InChI

1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

InChI key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Gene Information

human ... CYP2C9(1559), VKORC1(79001)

Description

Biochem/physiol Actions

Prototype of the 4-hydroxycoumarin class of anticoagulants, which act as vitamin K antagonists, preventing formation of prothrombin. There are many reports that dicumarol also inhibits NADPH:quinone oxidoreductase (NQO(1)). In one, it inhibited NQO(1) in a pancreatic cancer cell line, causing increased formation of superoxide and inhibiting cell growth.