M1390

3,3′-Methylene-bis(4-hydroxycoumarin)

• Synonym(s): Bishydroxycoumarin, Dicoumarol, Dicumarol
• Empirical Formula (Hill Notation): C₁₉H₁₂O₆
• CAS Number: 66-76-2
• Molecular Weight: 336.29
• EC Number: 200-632-9
• MDL number: MFCD00006857
• UNSPSC Code: 12352103
• PubChem Substance ID: 24896643
• NACRES: NA.47

Properties

• biological source: synthetic (organic)
• Quality Level: 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.

Safety Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301,H372,H411
• Precautionary Statements: P260 - P264 - P273 - P301 + P310 - P314 - P391
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves