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D223204

Sigma-Aldrich

Duroquinone

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
Molecular Weight:
164.20
Beilstein:
1909128
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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 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

Certificates of Analysis (COA)

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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)
H L Reeve et al.
The Journal of physiology, 533(Pt 1), 253-261 (2001-05-15)
How the ductus arteriosus (DA) closes at birth remains unclear. Inhibition of O2-sensitive K+ channels may initiate the closure but the sensor mechanism is unknown. We hypothesized that changes in endogenous H2O2 could act as this sensor. Using chemiluminescence measurements
P Lagrange et al.
Free radical biology & medicine, 27(5-6), 667-672 (1999-09-18)
In the present study, we investigated the changes in blood-brain barrier (BBB) permeability following brain endothelial cell exposure to different xenobiotics able to promote free radical generation during their metabolism. Our in vitro BBB model consisted of confluent monolayers of
Said H Audi et al.
American journal of physiology. Lung cellular and molecular physiology, 285(5), L1116-L1131 (2003-07-29)
The lungs can substantially influence the redox status of redox-active plasma constituents. Our objective was to examine aspects of the kinetics and mechanisms that determine pulmonary disposition of redox-active compounds during passage through the pulmonary circulation. Experiments were carried out
G J Wilde et al.
The European journal of neuroscience, 12(11), 3863-3870 (2000-11-09)
Upregulation of the pro-inflammatory cytokine tumour necrosis factor-alpha (TNF) occurs rapidly in the brain following ischaemia, although it is unclear whether this represents a neurotoxic or neuroprotective response. We have investigated whether TNF has different actions in the pre- and

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