6956-96-3

Basic information

• Product Name: DMNQ
• Synonyms: DMNQ;DIMENQ;2,3-DIMETHOXY-1,4-NAPHTHOQUINONE;RARECHEM BW GA 0209;1,4-Naphthalenedione, 2,3-dimethoxy-;Nsc 69355;2,3-dimethoxynaphthalene-1,4-dione
• CAS NO: 6956-96-3
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.21
• EINECS: 604-604-1
• Mol File: 6956-96-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 392.5°C at 760 mmHg
• Flash Point: 177.6°C
• Appearance: /solid
• Density: 1.28g/cm³
• Vapor Pressure: 2.28E-06mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 5 mg/ml).
• Stability: Stable for 1 year as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: DMNQ(CAS DataBase Reference)
• NIST Chemistry Reference: DMNQ(6956-96-3)
• EPA Substance Registry System: DMNQ(6956-96-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 6956-96-3(Hazardous Substances Data)

Usage

Description

DMNQ is a 1,4-naphthoquinone that acts as a redox-cycling agent, typically increasing intracellular superoxide and hydrogen peroxide formation. The amount of oxidative stress is proportional to the amount of DMNQ applied and can alter diverse cellular parameters, including signal transduction, mitochondrial function, and gene expression.

Uses

Different sources of media describe the Uses of 6956-96-3 differently. You can refer to the following data:
1. DMNQ is a non-alkylating redox cycling quinone.
2. 2,3-Dimethoxy-1,4-naphthoquinone has been used to investigate the effects of ethanol on podocyte apoptosis under hypoxic and hyperoxic conditions.

Definition

ChEBI: A naphthoquinone that is 1,4-naphthoquinone bearing two methoxy substituents at positions 2 and 3. Redox-cycling agent that induces intracellular superoxide anion formation and, depending on the concentration, induces cell proliferation, apoptosis or necro is. Used to study the role of ROS in cell toxicity, apoptosis, and necrosis.

Biochem/physiol Actions

2,3-dimethoxy-1,4-naphthoquinone (DMNQ) has the ability to produce H2O2?through redox cycling but fails to conjugate with glutathione (GSH).

References

References/Citations 1) Gant?et al. (1988)?Redox Cycling and Sulphydryl Arylation; Their Relative Importance in the Mechanism of Quinone Cytotoxicity to Isolated Hepatocytes; Chem. Biol. Interactions;?65?157 2) Stubberfield and Cohen (1989)?Interconversion of NAD(H) to NADP(H). A cellular response to quinone-induced oxidative stress in isolated hepatocytes; Biochem. Pharmacol.,?38?2631 3) Dypbukt?et al?(1994)?Different prooxidant levels stimulate growth, trigger apoptosis or produce necreosis of insulin-secreting RINm5F cells. The role of intracellular polyamines; J. Biol. Chem.,?269?30553 4) Henry and Wallace (1996)?Differential mechanisms of cell killing by redox cycling and arylating quinones; Arch. Toxicol.,?70?482

InChI:InChI=1/C12H10O4/c1-15-11-9(13)7-5-3-4-6-8(7)10(14)12(11)16-2/h3-6H,1-2H3

Upstream product

• 19774-34-6 (E)-1-ethoxybuta-1,3-diene 
• 3117-02-0 2,3-dimethoxy-1,4-benzoquinone 
• 1515-76-0 1-acetoxybuta-1,3-diene 
• 67-56-1 methanol 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 124-41-4 sodium methylate 
• 15707-32-1 2-chloro-3-methoxy-1,4-naphthoquinone 
• 98122-97-5 2,3-dimethoxy-4-hydroxy-4-phenyl-2-cyclobuten-1-one 
• 5150-42-5 2,3-dimethoxyphenol 
• 130-15-4 [1,4]naphthoquinone 
• 186581-53-3 diazomethane 
• 605-37-8 isonaphthazarine 

Downstream Products

• 1421252-50-7 2-bis(4-tert-butylbenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-48-3 2-bis(4-fluorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-42-7 2-bis(4-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-44-9 2-bis(3-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-46-1 2-bis(2-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-40-5 2-dibenzoylamino-3-methoxy-1,4-naphthoquinone 

Relevant articles and documents

Studies on quinones. Part 43: Synthesis and cytotoxic evaluation of polyoxyethylene-containing 1,4-naphthoquinones

A series of naphthoquinones 2,3-disubstituted with chlorine and oxyethylene groups have been prepared from 2,3-dichloro- and 2,3-dimethoxy-1,4-naphthoquinone. The members of these series were tested on normal human fibroblasts and on a panel of four human cancer cell lines. Antitumor activities, which were in the range of IC50 1.3-89.5 μM, discussed in terms of LUMO energy, lipophilicity and size of the polyoxyethylene moiety.

A new 2,3-dimethoxy-1,4-naphthoquinone redox anolyte for non-aqueous organic static redox battery

Redox flow batteries (RFB) are the choice for grid-level large-scale energy storage applications. Especially, the non-aqueous variant of RFB is considered for its unique advantages such as low cost, diverse engineering possibility of redox molecules, and

Method for inhibiting Trypanosoma cruzi

Methods are provided to inhibit proliferation of Trypanosoma cruzi with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can be used to provide prophylaxis or treatment to a patient in