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D223204

Sigma-Aldrich

Duroquinone

97%

Sinónimos:

2,3,5,6-Tetramethyl-1,4-benzoquinone, Tetramethyl-p-benzoquinone

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About This Item

Fórmula empírica (notación de Hill):
C10H12O2
Número de CAS:
527-17-3
Peso molecular:
164.20
Beilstein/REAXYS Number:
1909128
EC Number:
208-409-8
MDL number:
MFCD00001604
UNSPSC Code:
12352100
PubChem Substance ID:
24893666
NACRES:
NA.22

assay

97%

form

powder

mp

110-112 °C (lit.)

SMILES string

CC1=C(C)C(=O)C(C)=C(C)C1=O

InChI

1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3

InChI key

WAMKWBHYPYBEJY-UHFFFAOYSA-N

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General description

Duroquinone is an organic oxidant that belongs to the class of 1,4-benzoquinones, is used in redox flow Li–O2 batteries.

Application

  • Role of Duroquinone in Photosynthetic Research: A study on purple bacterial photosynthetic reaction centers highlighted Duroquinone′s role when incorporated into the QA binding site, impacting the isotope edited FTIR difference spectra, crucial for understanding energy conversion processes in photosynthesis (Zhao et al., 2013).
  • Duroquinone as a Molecular Ion Source: Research demonstrated the generation of molecular negative ions by Duroquinone, showcasing its potential in mass spectrometry applications for studying molecular ionization and longevity (Khvostenko et al., 2012).
  • Duroquinone in Biochemical Sensors: Investigation into the optimization of gold electrode surfaces with photosystem II monolayers revealed Duroquinone′s critical role in enhancing sensor responses, applicable in biochemical sensor technology (Maly et al., 2005).
  • Cytotoxicity of Duroquinone Congeners: A comparative study of 14 p-benzoquinone congeners, including Duroquinone, used quantitative structure-toxicity relationships to evaluate cytotoxicity in rat hepatocytes and PC12 cells, relevant for safety assessments in chemical manufacturing (Siraki et al., 2004).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Revealing the catalytic pathway of a quinone-mediated oxygen reduction reaction in aprotic Li--O 2 batteries
Wu S, et al.
Journal of the Chemical Society. Chemical Communications, 58, 1025-1028 (2022)
Said H Audi et al.
American journal of physiology. Lung cellular and molecular physiology, 289(5), L788-L797 (2005-07-05)
NAD(P)H:quinone oxidoreductase 1 (NQO1) plays a dominant role in the reduction of the quinone compound 2,3,5,6-tetramethyl-1,4-benzoquinone (duroquinone, DQ) to durohydroquinone (DQH2) on passage through the rat lung. Exposure of adult rats to 85% O2 for > or =7 days stimulates
R A Rothery et al.
Biochemistry, 40(17), 5260-5268 (2001-04-25)
We have investigated the functional relationship between three of the prosthetic groups of Escherichia coli nitrate reductase A (NarGHI): the two hemes of the membrane anchor subunit (NarI) and the [3Fe-4S] cluster of the electron-transfer subunit (NarH). In two site-directed
J Maly et al.
Analytical and bioanalytical chemistry, 381(8), 1558-1567 (2005-04-12)
Mass transport of the bulk of the analyte to the electrode and through the bioactive layer can be significantly improved by use of the nanoelectrode array and defined arrangement of protein film. This phenomenon has been studied by (i) atomic-force
Marilyn P Merker et al.
American journal of physiology. Lung cellular and molecular physiology, 290(3), L607-L619 (2005-10-26)
The objective of this study was to examine the impact of chronic hyperoxic exposure (95% O2 for 48 h) on intact bovine pulmonary arterial endothelial cell redox metabolism of 2,3,5,6-tetramethyl-1,4-benzoquinone (duroquinone, DQ). DQ or durohydroquinone (DQH2) was added to normoxic
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