66-76-2
Dicumarol
CAS: 66-76-2
Molecular Formula: C19H12O6
66-76-2 - Names and Identifiers
| Name | Dicumarol |
| Synonyms | DICUMAROL Dicumarol BISCUMAROL DICOUMARIN DICOUMAROL BIS-HYDROXYCOUMARIN 3,3'-methylen-bis(4-hydroxy-cumarin) 3,3'-methyleen-bis(4-hydroxy-cumarine) 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- |
| CAS | 66-76-2 |
| EINECS | 200-632-9 |
| InChI | InChI=1/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 |
66-76-2 - Physico-chemical Properties
| Molecular Formula | C19H12O6 |
| Molar Mass | 336.3 |
| Density | 1.2864 (rough estimate) |
| Melting Point | 290-292°C(lit.) |
| Boling Point | 392.79°C (rough estimate) |
| Flash Point | 231.949°C |
| Water Solubility | Soluble in aqueous alkaline solutions, organic bases, 0.1 N NaOH (15 mg/ml), Pyridine (50 mg/ml), chloroform (slightly soluble), and benzene (slightly soluble). Insoluble in water, and alcohols. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Fine Crystalline Powder |
| Color | White |
| Merck | 14,3090 |
| pKa | 4.20±1.00(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.4450 (estimate) |
| In vitro study | Dicoumarol is an inhibitor of both NAD(P)H:quinone oxidoreductase 1 (NQO1) and PDK1 with IC 50 s of 0.37±0.15 and 19.42±0.032 μM, respectively. The PDK1 activity is inhibited by Dicoumarol in a dose-dependent manner. The enzymatic activity of PDK1 is reduced by approximately 94% when treated with 200 μM Dicoumarol. Dicoumarol decreases the p-PDHA1 level by 26% (100 μM Dicoumarol) and by 72% (200 μM Dicoumarol), with no statistical difference in the total PDHA1 level. Both 100 μM and 200 μM Dicoumarol markedly induce apoptosis of SKOV3 cells. Similarly, flow cytometric analysis of annexin V + PI + cells reveals that 100 μM and 200 μM Dicoumarol treatments generate approximately 20.87% and 24.94% apoptotic cells, respectively, significantly higher than vehicle treatment. It is also observed that treatment of MCF-7-TAMR cells with Dicoumarol, a known NQO1 inhibitor, reverses their tamoxifen-resistance phenotype. |
| In vivo study | Dichloroacetate (DCA) at 100 mg/kg, Dicoumarol at 30 mg/kg, and Dicoumarol at 50 mg/kg all significantly reduce tumor volume and decrease tumor weight, when compare to tumors from control or vehicle groups. Total caspase-3 and total anti-poly (ADP-ribose) polymerase (PARP) are significantly decreased in Dicoumarol-treated SKOV3 xenografts, when compare to tumors from the control or vehicle group. |
66-76-2 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R48/25 - R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S37 - Wear suitable gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | GN7875000 |
| TSCA | Yes |
| HS Code | 29322985 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 541.6 mg/kg (Rose) |
66-76-2 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Dicoumarol is a competitive NADPH quinone oxidoreductase (NQO1) inhibitor, which can be used as an anticoagulant by interfering with the metabolism of vitamin K. |
| Target | Value |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 250 mg/kg; Oral-mouse LD50: 233 mg/kg |
| flammability hazard characteristics | smoke stimulated by thermal decomposition; The effect of drugs on reproductive system: stillbirth, teratogenesis, poor baby; Drug overdose bleeding |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:04
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QQ: 2853786052
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