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M1390

3,3′-Methylene-bis(4-hydroxycoumarin)

Synonyme(s) :

Bishydroxycoumarin, Dicoumarol, Dicumarol

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A propos de cet article

Formule empirique (notation de Hill) :
C19H12O6
Numéro CAS:
66-76-2
Poids moléculaire :
336.29
NACRES:
NA.47
PubChem Substance ID:
24896643
UNSPSC Code:
12352103
EC Number:
200-632-9
MDL number:
MFCD00006857
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biological source

synthetic (organic)

Quality Level

100

assay

≥98% (TLC)

form

powder

mp

290-292 °C (lit.)

solubility

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

SMILES string

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

InChI key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Gene Information

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

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.

signalword

Danger

Hazard Classifications

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

Classe de stockage

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCR2107
MKCQ4709
MKCN6260
MKCL6230
MKCH6411

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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
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
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