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D5439

Sigma-Aldrich

2,3-Dimethoxy-1,4-naphthoquinone

≥99%, solid

Synonym(s):

DMNQ

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About This Item

Empirical Formula (Hill Notation):
C12H10O4
CAS Number:
Molecular Weight:
218.21
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Related Categories

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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)
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
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
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
Valerie P Wright et al.
The Journal of physiology, 587(Pt 23), 5767-5781 (2009-10-21)
Skeletal muscles produce transient reactive oxygen species (ROS) in response to intense stimulation, disuse atrophy, heat stress, hypoxia, osmotic stress, stretch and cell receptor activation. The physiological significance is not well understood. Protein phosphatases (PPases) are known to be highly

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