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M1390

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

EC Number:

200-632-9

MDL number:

MFCD00006857

UNSPSC Code:

12352103

PubChem Substance ID:

24896643

NACRES:

NA.47

biological source

synthetic (organic)

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)

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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.

Pictograms

GHS06,GHS08,GHS09

Signal Word

Danger

Hazard Statements

H301,H372,H411

Precautionary Statements

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

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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Progesterone is required for maintenance of pregnancy, and peripheral concentrations of progesterone are affected by both production and inactivation. Hepatic cytochrome P450 (EC 1.14.14.1) and aldo-keto reductase (EC 1.1.1.145-151) enzymes play a pivotal role in the first step of steroid

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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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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

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Yi-Ting Wu et al.

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β-Lapachone has antitumor and wound healing-promoting activities. To address the potential influences of various chemicals on heart development of zebrafish embryos, we previously treated zebrafish embryos with chemicals from a Sigma LOPAC1280™ library and found several chemicals including β-lapachone that

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