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287897 Dicoumarol - CAS 66-76-2 - Calbiochem

287897
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Overview

Replacement Information

Key Spec Table

Empirical FormulaCAS #
C₁₉H₁₂O₆66-76-2

Products

Catalogue NumberPackaging Qty/Pack
287897-500MG Glass bottle 500 mg
Description
OverviewA cell-permeable quinone reductase inhibitor with anticoagulant properties. Potentiates apoptosis by simultaneously blocking SAPK/JNK and NF-κB pathways. Does not affect phosphorylation of p38 or activation of AKT. Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells (IC50 = 180 µM and 150 µM, respectively).
Catalogue Number287897
Brand Family Calbiochem®
Synonyms3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
References
ReferencesSeanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 103.
Krause, D., et al. 2001. J. Biol. Chem. 276, 19244.
Pink, J.J., et al. 2000. J. Biol. Chem. 275, 5416.
Cross, J.V., et al. 1999. J. Biol. Chem. 274, 31150.
Morrow, C.S., et al. 1998. J. Biol. Chem. 273, 20114.
Weigert, R., et al. 1997. J. Biol. Chem. 272, 14200.
Product Information
CAS number66-76-2
ATP CompetitiveN
FormWhite solid
Hill FormulaC₁₉H₁₂O₆
Chemical formulaC₁₉H₁₂O₆
ReversibleN
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary TargetBlocks brefeldin A-dependent mono-ADP-ribosylation in vitro
Primary Target IC<sub>50</sub>180 µM and 150 µM in blocking brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells, respectively
Purity≥98% by titration
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
RTECSGN7875000
Safety Information
R PhraseR: 22-48/25-51/53

Harmful if swallowed.
Toxic: danger of serious damage to health by prolonged exposure if swallowed.
Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S PhraseS: 37-45-61

Wear suitable gloves.
In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Avoid release to the environment. Refer to special instructions/safety data sheet.
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Toxic & Carcinogenic / Teratogenic
Hazardous Materials Attention: Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Storage +2°C to +8°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsUnstable in solution; reconstitute just prior to use.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications

Documentation

Dicoumarol - CAS 66-76-2 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

Dicoumarol - CAS 66-76-2 - Calbiochem Certificates of Analysis

TitleLot Number
287897

References

Reference overview
Seanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 103.
Krause, D., et al. 2001. J. Biol. Chem. 276, 19244.
Pink, J.J., et al. 2000. J. Biol. Chem. 275, 5416.
Cross, J.V., et al. 1999. J. Biol. Chem. 274, 31150.
Morrow, C.S., et al. 1998. J. Biol. Chem. 273, 20114.
Weigert, R., et al. 1997. J. Biol. Chem. 272, 14200.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision04-January-2010 RFH
Synonyms3,3ʹ-Methylenebis(4-hydroxycoumarin), Bishydroxycoumarin, Dicumarol
DescriptionA cell-permeable quinone reductase inhibitor with anti-coagulant properties. Binds competitively with NADH or NADPH to inhibit NAD(P)H:quinone oxidoreductase (NQO1). Shown to inhibit IGF-I-, menadione-, and DMNQ-mediated activation of stress-activated protein kinase/c-jun NH2-terminal kinase (SAPK/JNK) and subsequent phosphorylation of c-Jun, as well as stress-induced activation (hypertonic sorbitol) of SAPK/JNK. Does not affect p38 phosphorylation or protein kinase B (AKT) activation. Also shown to induce apoptosis in MCF7 breast carcinoma cells. Inhibits glutathione-S transferase (GST) A1-1 enzyme (Kiu = 4.4 µM, Kic = 3.6 µM) in vitro and in MCF7/VPα cells (a multidrug resistant derivative of MCF7 transfected with GST A1-1). Blocks brefeldin A-dependent mono-ADP-ribosylation in vitro and Golgi disassembly in living cells (IC50 = 180 µM and 150 µM, respectively).
FormWhite solid
Intert gas (Yes/No) Packaged under inert gas
CAS number66-76-2
RTECSGN7875000
Chemical formulaC₁₉H₁₂O₆
Structure formulaStructure formula
Purity≥98% by titration
Solubility0.1 N NaOH (15 mg/ml) or Pyridine (50 mg/ml)
Storage +2°C to +8°C
Protect from light
Do Not Freeze Ok to freeze
Special InstructionsUnstable in solution; reconstitute just prior to use.
Toxicity Toxic & Carcinogenic / Teratogenic
Merck USA index14, 3090
ReferencesSeanor, K.L., et al. 2003. Antioxid. Redox. Signal 5, 103.
Krause, D., et al. 2001. J. Biol. Chem. 276, 19244.
Pink, J.J., et al. 2000. J. Biol. Chem. 275, 5416.
Cross, J.V., et al. 1999. J. Biol. Chem. 274, 31150.
Morrow, C.S., et al. 1998. J. Biol. Chem. 273, 20114.
Weigert, R., et al. 1997. J. Biol. Chem. 272, 14200.