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DICUMAROL

Product Name
DICUMAROL
CAS No.
66-76-2
Chemical Name
DICUMAROL
Synonyms
DICOUMAROL;DICOUMARIN;nc034;Melitoxin;Cuma;Cumid;Acadyl;Acavyl;Dicuman;Dicumol
CBNumber
CB9224757
Molecular Formula
C19H12O6
Formula Weight
336.3
MOL File
66-76-2.mol
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DICUMAROL Property

Melting point:
290-292 °C(lit.)
Boiling point:
392.79°C (rough estimate)
Density 
1.2864 (rough estimate)
refractive index 
1.4450 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO:3.06(Max Conc. mg/mL);9.1(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.49(Max Conc. mM)
DMF:1.25(Max Conc. mg/mL);3.72(Max Conc. mM)
Water:50.0(Max Conc. mg/mL);148.68(Max Conc. mM)
form 
Fine Crystalline Powder
pka
4.20±1.00(Predicted)
color 
White
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.
Merck 
14,3090
EPA Substance Registry System
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (66-76-2)
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Safety

Hazard Codes 
T,N
Risk Statements 
22-48/25-51/53
Safety Statements 
37-45-61
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
GN7875000
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29322985
Hazardous Substances Data
66-76-2(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 541.6 mg/kg (Rose)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M1390
Product name
3,3′-Methylene-bis(4-hydroxycoumarin)
Packaging
5g
Price
$33.12
Updated
2024/03/01
Sigma-Aldrich
Product number
287897
Product name
Dicoumarol
Packaging
500mg
Price
$85.2
Updated
2024/03/01
TCI Chemical
Product number
M0216
Product name
Dicoumarol
Packaging
1G
Price
$34
Updated
2024/03/01
TCI Chemical
Product number
M0216
Product name
Dicoumarol
Packaging
25G
Price
$315
Updated
2024/03/01
Alfa Aesar
Product number
J63634
Product name
Dicumarol
Packaging
5g
Price
$33.65
Updated
2024/03/01
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DICUMAROL Chemical Properties,Usage,Production

Description

The plants containing dicoumarol mainly include red carnation grass (Trifolium pratense L., hongchezhoucao), rotten alfalfa (Medicago sativa L., zimuxu), rotten white vanilla rhinoceros (Melilotus albus Desr., baixiangcaomuxi), and other plants in Leguminosae.

Description

Dicoumarol is a competitive inhibitor of NADH:quinone oxidoreductase (NQO1) with IC50 values of 2.6 and 404 nM in the absence and presence of 2 μM BSA, respectively. It has antiproliferative activity against MIA PaCa-2 pancreas and HCT116 colon carcinoma cells (IC50s = 52 and 19 μM, respectively, after a 96 hour incubation). Dicoumarol inhibits stress-activated protein kinase (SAPK) in HEK293 cells (IC50 = 19-33 μM) at a point upstream of MEKK1 and downstream of TNF receptor-associated factor 2 (TRAF2), and it inhibits TNF-α and LPS-induced NF-κB activation in HeLa cells. It also has antiproliferative activity against FL5.12 lymphocytic and MCF-7 breast carcinoma cells (100 μM) by suppressing JNK activation.

Chemical Properties

white fine crystalline powder

Physical properties

Appearance: white or milky white crystalline powder, slightly fragran; Solubility: not dissolved in water, ethanol, and ether, slightly dissolved in chloroform, dissolved in alkali solution; Melting point: 287–293?°C.?It can be bluer or with purple fluorescence in the ultraviolet light.

History

In 1940, Karl Paul Link, a fertile scientist from the University of Wisconsin in the United States, first isolated the anticoagulant substance from the moldy alfalfa (Melilotus) and determined its structure. It is a kind of dicoumaroloid substance, combined by two molecules of coumarin substances. Since this material was found in the first few years, it has been used as a rodenticide .
In 1979, Conrad et?al. reacted p-nitrobenzene ketone with 4-hydroxycoumarin to obtain vinegar coumarin, which is basically the same as warfarin in anticoagulant, but its metabolites also have anticoagulant effect, so the duration of anticoagulation is longer than warfarin.

Uses

Dicumarol is a natural chemical used as an anticoagulant agents that functions as a vitamin K antagonist and is also a derivative of Coumarin.

Uses

This drug is used for preventing and treating thrombosis, thrombophlebitis, thromboemolium, and for preventing thrombo-formation in post-operational periods.

Indications

Intravascular thromboembolic diseases include postoperative or postoperative thrombotic phlebitis, pulmonary embolism, myocardial infarction, and atrial fibrillation caused by embolism.

Definition

ChEBI: A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group.

General Description

Dicumarol, 3,3'-methylenebis[4-hydroxycoumarin],is a white or creamy white crystalline powderwith a faint, pleasant odor and a slightly bitter taste. It ispractically insoluble in water or alcohol, slightly soluble inchloroform, and dissolved readily by solutions of fixed alkalies.The effects after administration require 12 to 72 hours todevelop and persist for 24 to 96 hours after discontinuance.

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.

Pharmacology

Dicoumarin is an oral anticoagulant drug and is invalid in?vitro . Dicoumarin is a coumarin derivative, and its common mechanism is to inhibit synthesis of the coagulation factor in the liver. The structure of dicoumarin is similar to that of vitamin K and is an antagonist or a competitive inhibitor of vitamin K.?It binds to the vitamin K epoxide reductase in the liver, inhibits the conversion of vitamin K from epoxide to hydroquinone, and inhibits the recycling of vitamin K, resulting in that the glutamate side chain of vitamin K-dependent coagulation factors II, VII, IX, and X cannot be carboxylated by γ-carboxy glutamate groups, affecting the binding of coagulation factor with calcium ion, and thereby inhibiting coagulation, reducing platelet adhesion, and prolonging thrombosis time . Dicoumarol drugs have no direct confrontation with synthesized prothrombin and coagulation factor, so it is ineffective in?vitro. After withdrawal of dicoumarin, prothrombin and coagulation factors II, IV, IX, and X gradually restore to a certain level, and hence the anticoagulant effect disappear, so its efficacy can be maintained for a long time .

Pharmacokinetics

Dicoumarol is not completely absorbed in the gastrointestinal tract, often is associated with gastrointestinal discomfort, and is very rarely used clinically. Today, the only coumarin used in the United States is warfarin, but phenprocoumon and acenocomumarol are used in Europe.

Clinical Use

Dicumarol is used alone or as an adjunct to heparin in theprophylaxis and treatment of intravascular clotting. It is usedin postoperative thrombophlebitis, pulmonary embolus, acuteembolic and thrombotic occlusion of peripheral arteries, andrecurrent idiopathic thrombophlebitis. It has no effect on analready-formed embolus but may prevent further intravascularclotting. Because the outcome of acute coronary thrombosisdepends largely on extension of the clot and formation ofmural thrombi in the heart chambers, with subsequent embolization,dicumarol has been used in this condition. It hasalso been administered to arrest impending gangrene afterfrostbite. The dose, after determination of the prothrombinclotting time, is 25 to 200 mg, depending on the size and thecondition of the patient. The drug is given orally in the formof capsules or tablets. On the second day and thereafter, itmay be given in amounts sufficient to maintain the prothrombinclotting time at about 30 seconds. If hemorrhages shouldoccur, a dosage of 50 to 100 mg of menadione sodium bisulfiteis injected, supplemented by a blood transfusion.

Side effects

The most serious adverse reaction of warfarin is bleeding, which can be against by vitamin K, and if necessary, fresh plasma or whole blood can be injected into the body to confront bleeding .

Synthesis

Dicoumarol, 3,3??-methylene-bis(4-hydroxycoumarin) (24.1.8), is synthesized from 4-hydroxycoumarine (24.1.7), which is in turn synthesized from salicylic acid methyl ester by cyclization to a chromone derivative using sodium or sodium methoxide; or from o-oxyacetophenone by reacting it with diethylcarbonate in the presence of sodium ethoxide. Condensation of the resulting 4-hydroxycoumarin with formaldehyde as a phenol component gives dicoumarol.

DICUMAROL Preparation Products And Raw materials

Raw materials

Preparation Products

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DICUMAROL Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44688
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Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
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LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
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70
Tianjin heowns Biochemical Technology Co., Ltd.
Tel
400 638 7771
Email
sales@heowns.com
Country
China
ProdList
14435
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Chengdu Climax Biotech Co., Ltd.
Tel
028-83311324 1278112614
Fax
028-83311324
Email
climaxbiotech@gmail.com
Country
China
ProdList
925
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Thermo Fisher Scientific
Tel
800-810-5118
Fax
+86-10-84193589
Email
cnchemical@thermofisher.com
Country
China
ProdList
17770
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Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
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58
Beijing innoChem Science & Technology Co.,Ltd.
Tel
400-810-7969 010-59572699
Fax
010-59572688
Email
ningzi.li@inno-chem.com.cn
Country
China
ProdList
6134
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View Lastest Price from DICUMAROL manufacturers

Dideu Industries Group Limited
Product
DICUMAROL 66-76-2
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-08-04
Career Henan Chemical Co
Product
DICUMAROL 66-76-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
25kg
Release date
2019-07-12

66-76-2, DICUMAROLRelated Search:


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