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3,3′-Methylene-bis(4-hydroxycoumarin)

Name: 3,3′-Methylene-bis(4-hydroxycoumarin)
Brand: SIGMA

Synonym(s):

Bishydroxycoumarin, Dicoumarol, Dicumarol

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₂O₆

CAS Number:

66-76-2

Molecular Weight:

336.29

NACRES:

NA.47

PubChem Substance ID:

24896643

UNSPSC Code:

12352103

EC Number:

200-632-9

MDL number:

MFCD00006857

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Properties

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)

Description

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.

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This Item	D5782	C9375	287897
Sigma-Aldrich M1390 3,3′-Methylene-bis(4-hydroxycoumarin)	Sigma-Aldrich D5782 2′,3′-Dideoxycytidine	Sigma-Aldrich C9375 5-Carboxy-2-thiouracil	Sigma-Aldrich 287897 Dicoumarol
biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)	biological source -
assay ≥98% (TLC)	assay ≥98% (HPLC)	assay ≥98% (TLC)	assay ≥98% (titration)
Gene Information human ... CYP2C9(1559), VKORC1(79001)	Gene Information -	Gene Information -	Gene Information -
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 100
form powder	form powder	form powder	form solid
solubility pyridine: 50 mg/mL, clear, faintly yellow to brownish-yellow	solubility water: 50 mg/mL, clear, colorless to faintly yellow	solubility 1 M NaOH: 50 mg/mL, clear, colorless to faintly yellow	solubility 0.1 M NaOH: 15 mg/mL, pyridine: 50 mg/mL

pictograms

GHS06,GHS08,GHS09

signalword

Danger

hcodes

H301,H372,H411

pcodes

P260 - P264 - P273 - P301 + P310 - P314 - P391

Hazard Classifications

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

Storage Class

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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Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular generation of superoxide.

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

Inhibitors of NQO1: identification of compounds more potent than dicoumarol without associated off-target effects.

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

Pharmacological inhibitors of NAD(P)H quinone oxidoreductase, NQO1: structure/activity relationships and functional activity in tumour cells.

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

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Global Trade Item Number

SKU	GTIN
M1390-25G	04061834038276
M1390-5G	04061834038290

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