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    Dicumarin Produkt Beschreibung

    DICUMAROL Struktur
    66-76-2
    CAS-Nr.
    66-76-2
    Bezeichnung:
    Dicumarin
    Englisch Name:
    DICUMAROL
    Synonyma:
    Cuma;Cumid;nc034;Acadyl;Acavyl;Dicuman;Dicumol;Kumoran;Dicoumal;Dufalone
    CBNumber:
    CB9224757
    Summenformel:
    C19H12O6
    Molgewicht:
    336.3
    MOL-Datei:
    66-76-2.mol

    Dicumarin Eigenschaften

    Schmelzpunkt:
    290-292 °C(lit.)
    Siedepunkt:
    392.79°C (rough estimate)
    Dichte
    1.2864 (rough estimate)
    Brechungsindex
    1.4450 (estimate)
    storage temp. 
    Sealed in dry,Room Temperature
    Aggregatzustand
    Fine Crystalline Powder
    pka
    4.20±1.00(Predicted)
    Farbe
    White
    Wasserl?slichkeit
    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 chemische Informationen
    2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (66-76-2)
    Sicherheit
    • Risiko- und Sicherheitserkl?rung
    • Gefahreninformationscode (GHS)
    Kennzeichnung gef?hrlicher T,N
    R-S?tze: 22-48/25-51/53
    S-S?tze: 37-45-61
    RIDADR  UN 2811 6.1/PG 3
    WGK Germany  3
    RTECS-Nr. GN7875000
    TSCA  Yes
    HazardClass  6.1(b)
    PackingGroup  III
    HS Code  29322985
    Giftige Stoffe Daten 66-76-2(Hazardous Substances Data)
    Toxizit?t LD50 orally in rats: 541.6 mg/kg (Rose)
    Bildanzeige (GHS)
    Alarmwort Achtung
    Gefahrenhinweise
    Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
    H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
    H372 Sch?digt bei Hautkontakt und Verschlucken die Organe bei l?ngerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizit?t (wiederholte Exposition) Kategorie 1 Achtung P260, P264, P270, P314, P501
    H411 Giftig für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 2
    Sicherheit
    P260 Dampf/Aerosol/Nebel nicht einatmen.
    P264 Nach Gebrauch gründlich waschen.
    P264 Nach Gebrauch gründlich waschen.
    P270 Bei Gebrauch nicht essen, trinken oder rauchen.
    P273 Freisetzung in die Umwelt vermeiden.
    P314 Bei Unwohlsein ?rztlichen Rat einholen / ?rztliche Hilfe hinzuziehen.

    Dicumarin Chemische Eigenschaften,Einsatz,Produktion Methoden

    R-S?tze Betriebsanweisung:

    R22:Gesundheitssch?dlich beim Verschlucken.
    R48/25:Giftig: Gefahr ernster Gesundheitssch?den bei l?ngerer Exposition durch Verschlucken.
    R51/53:Giftig für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.

    S-S?tze Betriebsanweisung:

    S37:Geeignete Schutzhandschuhe tragen.
    S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
    S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.

    Beschreibung

    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.

    Beschreibung

    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.

    Chemische Eigenschaften

    white fine crystalline powder

    Physikalische Eigenschaften

    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.

    Verwenden

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

    Verwenden

    anticoagulant

    Verwenden

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

    Definition

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

    Indications

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

    Allgemeine Beschreibung

    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.

    Pharmakokinetik

    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.

    Pharmakologie

    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 .

    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.

    Nebenwirkungen

    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 .

    Chemical 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.

    Dicumarin Upstream-Materialien And Downstream Produkte

    Upstream-Materialien

    Downstream Produkte


    Dicumarin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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    66-76-2(Dicumarin)Verwandte Suche:


    • BIS-HYDROXYCOUMARIN
    • BISCUMAROL
    • DICUMAROL
    • DICOUMARIN
    • DICOUMAROL
    • 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-
    • 3,3’-methyleen-bis(4-hydroxy-cumarine)
    • 3,3’-methylen-bis(4-hydroxy-cumarin)
    • 3,3’-methylenebis(4-hydroxy-1,2-benzopyrone)
    • 3,3’-methylenebis(4-hydroxy-2h-1-benzopyran-2-on
    • 3,3’-methylenebis(4-hydroxy-2h-1-benzopyran-2-one)
    • 3,3’-methylenebis(4-hydroxy-coumari
    • 3,3’-methylene-bis(4-hydroxycoumarine)
    • 3,3’-methylene-bis(4-hydroxycoumarine)(french)
    • 3,3’-methylenebis[4-hydroxy-2h-1-benzopyran-2-on
    • 3,3’-metilen-bis(4-idrossi-cumarina)
    • 3,3'-Methyleen-bis(4-hydroxy-cumarine)
    • 3,3'-Methylen-bis(4-hydroxy-cumarin)
    • 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
    • 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
    • 3,3'-Methylene-bis(4-hydroxycoumarine)
    • 3,3'-Metilen-bis(4-idrossi-cumarina)
    • 4,4’-dihydroxy-3,3’-methylenebiscoumarin
    • Acadyl
    • Acavyl
    • Antitrombosin
    • Baracoumin
    • Bis(4-hydroxycoumarin-3-yl)methane
    • Bis-3,3'-(4-hydroxycoumarinyl)methane
    • bis-3,3’-(4-hydroxycoumarinyl)methane
    • 3,3'-METHYLENEBIS(4-HYDROXYCOUMARIN)
    • 4-HYDROXY-3-[(4-HYDROXY-2-OXO-CHROMEN-3-YL)METHYL]CHROMEN-2-ONE
    • METHYLENEBISHYDROXYCOUMARIN
    • syringidin
    • dicoumarol 4,4'-dihydroxy-3,3'-methylenebis(2H-chromen-2-one)
    • 3,3μ-Methylenebis(4-hydroxycoumarin), Dicumarol
    • Dicumarol,99%
    • DicuMarol, 99% 5GR
    • Bishydroxycoumarin 3,3'-Methylenebis(4-hydroxycoumarin) Dicoumarin
    • 3,3'-Methylenebis
    • Dicumarol (200 mg)
    • 3,3'-Methylenebis(4-Hydroxy-2H-Chromen-2-One)
    • Dicoumarol - CAS 66-76-2 - Calbiochem
    • Coumarin, 3,3'-methylenebis(4-hydroxy-
    • Cuma
    • Cumid
    • Di-(4-hydroxy-3-coumarinyl)methane
    • di-4-hydroxy-3,3’-methylenedicoumarin
    • Di-4-hydroxy-3,3'-methylenedicoumarin
    • Dicoumal
    • Dicuman
    • Dicumaol R
    • dicumaolr
    • Dicumarine
    • Dicumol
    • Dikumarol
    • Dufalone
    • dwukumarol
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