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Documents

M1390

3,3′-Methylene-bis(4-hydroxycoumarin)

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

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

GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H301,H372,H411

Conseils de prudence

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

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)

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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

Effect of cytochrome P450 and aldo-keto reductase inhibitors on progesterone inactivation in primary bovine hepatic cell cultures.

C O Lemley et al.

Journal of dairy science, 93(10), 4613-4624 (2010-09-22)

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

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

β-Lapachone induces heart morphogenetic and functional defects by promoting the death of erythrocytes and the endocardium in zebrafish embryos.

Yi-Ting Wu et al.

Journal of biomedical science, 18, 70-70 (2011-09-23)

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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