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D5439

Sigma-Aldrich

2,3-Dimethoxy-1,4-naphthoquinone

≥99%, solid

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Synonym(s):
DMNQ
Empirical Formula (Hill Notation):
C12H10O4
CAS Number:
6956-96-3
Molecular Weight:
218.21
MDL number:
MFCD00184331
PubChem Substance ID:
24278374
NACRES:
NA.77

Quality Level

200

Assay

≥99%

form

solid

storage temp.

−20°C

SMILES string

COC1=C(OC)C(=O)c2ccccc2C1=O

InChI

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

InChI key

ZEGDFCCYTFPECB-UHFFFAOYSA-N

Application

2,3-Dimethoxy-1,4-naphthoquinone has been used to investigate the effects of ethanol on podocyte apoptosis under hypoxic and hyperoxic conditions.
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).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Acute ethanol induces apoptosis by stimulating TRPC6 via elevation of superoxide in oxygenated podocytes
Lu X Y, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(5), 965-974 (2015)
Toshiaki Teratani et al.
Free radical biology & medicine, 156, 45-56 (2020-06-20)
The nuclear receptor peroxisome proliferator-activated receptor (PPAR)γ has been implicated in the pathogenesis of various human diseases including fatty liver. Although nuclear translocation of PPARγ plays an important role in PPARγ signaling, details of the translocation mechanisms have not been
Richard Eugene Frye et al.
Scientific reports, 7(1), 4478-4478 (2017-07-02)
Mitoplasticity occurs when mitochondria adapt to tolerate stressors. Previously we hypothesized that a subset of lymphoblastoid cell lines (LCLs) from children with autistic disorder (AD) show mitoplasticity (AD-A), presumably due to previous environmental exposures; another subset of AD LCLs demonstrated
Tindaro M Giardina et al.
Biochimica et biophysica acta, 1777(2), 118-129 (2007-12-18)
Uncoupling protein-2 (UCP2) is a member of the inner mitochondrial membrane anion-carrier superfamily. Although mRNA for UCP2 is widely expressed, protein expression is detected in only a few cell types, including macrophages. UCP2 functions by an incompletely defined mechanism, to
Anne R Diers et al.
Redox biology, 1, 1-7 (2013-09-12)
Nitric oxide production by the endothelium is required for normal vascular homeostasis; however, in conditions of oxidative stress, interactions of nitric oxide with reactive oxygen species (ROS) are thought to underlie endothelial dysfunction. Beyond canonical nitric oxide signaling pathways, nitric
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