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M1390

Sigma-Aldrich

3,3′-Methylene-bis(4-hydroxycoumarin)

Synonyme(s) :

Bishydroxycoumarin, Dicoumarol, Dicumarol

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About This Item

Formule empirique (notation de Hill):
C19H12O6
Numéro CAS:
66-76-2
Poids moléculaire :
336.29
Numéro CE :
200-632-9
Numéro MDL:
MFCD00006857
Code UNSPSC :
12352103
ID de substance PubChem :
24896643
Nomenclature NACRES :
NA.47

Source biologique

synthetic (organic)

Pureté

≥98% (TLC)

Forme

powder

Pf

290-292 °C (lit.)

Solubilité

pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow

Chaîne SMILES 

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

Clé InChI

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Informations sur le gène

human ... CYP2C9(1559) , VKORC1(79001)

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Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazardEnvironment
GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H301,H372,H411

Classification des risques

Acute Tox. 3 Oral - Aquatic Chronic 2 - STOT RE 1 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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4-Nitroquinoline 1-oxide ≥98%

Sigma-Aldrich

N8141

4-Nitroquinoline 1-oxide

Resorufin sodium salt redox indicator

Sigma-Aldrich

R3257

Resorufin sodium salt

DT Diaphorase (NQO1) human lyophilized powder, recombinant, expressed in E. coli, ≥90% (SDS-PAGE)

Sigma-Aldrich

D1315

DT Diaphorase (NQO1) human

Katherine Ann Scott et al.
Biochemical pharmacology, 81(3), 355-363 (2010-10-26)
The enzyme NAD(P)H quinone oxidoreductase (NQO1) can function both as a detoxifying enzyme as well as chaperone protein. The latter property has been extensively characterized by the use of dicoumarol which inhibits the chaperone properties of NQO1 in cells. However
Alexandra Reichstein et al.
Journal of medicinal chemistry, 55(16), 7273-7284 (2012-08-01)
A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in
Karen Ann Nolan et al.
Biochemical pharmacology, 80(7), 977-981 (2010-07-06)
NAD(P)H quinone oxidoreductase (NQO1) has multiple functions in the cell including an ability to act as a detoxifying enzyme and as a protein chaperone. The latter property is particularly important in oncology as one of the client proteins of NQO1
An S Tan et al.
Free radical biology & medicine, 48(3), 421-429 (2009-11-26)
2,3-Dimethoxy 1,4-naphthoquinone (DMNQ), which redox cycles via two-electron reduction, mediates reduction of the cell-impermeative tetrazolium dye WST-1 in kidney epithelial cells (MDCK), which express high levels of NQO1, but not in HL60 or CHO cells, which are NQO1 deficient. DMNQ-dependent
Ying Dong et al.
Cancer research, 70(20), 8088-8096 (2010-10-14)
The clinical experimental agent, β-lapachone (β-lap; Arq 501), can act as a potent radiosensitizer in vitro through an unknown mechanism. In this study, we analyzed the mechanism to determine whether β-lap may warrant clinical evaluation as a radiosensitizer. β-Lap killed
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