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527-17-3,MFCD00001604
Catalog No.:AA003PTO
527-17-3 | 2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione
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Technical Information
Catalog Number:
AA003PTO
Chemical Name:
2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione
CAS Number:
527-17-3
Molecular Formula:
C10H12O2
Molecular Weight:
164.2011
MDL Number:
MFCD00001604
IUPAC Name:
2,3,5,6-tetramethylcyclohexa-2,5-diene-1,4-dione
InChI:
InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3
InChI Key:
WAMKWBHYPYBEJY-UHFFFAOYSA-N
SMILES:
CC1=C(C)C(=O)C(=C(C1=O)C)C
EC Number:
208-409-8
UNII:
X0Q8791R69
NSC Number:
2068
Properties
Computed Properties
 
Complexity:
268  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
164.084g/mol
Formal Charge:
0
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
164.204g/mol
Monoisotopic Mass:
164.084g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
34.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  

Synonyms
 
2,3,5,6-tetramethylbenzoquinone 
duroquinone 
2,3,5,6-Tetramethylbenzoquinone 
p-Benzoquinone, tetramethyl- 
p-Benzoquinone, 2,3,5,6-tetramethyl- 
2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetramethyl- 
2,3,5,6-Tetramethyl-p-benzoquinone 
NSC 2068 
CCRIS 2989 
p-Benzoquinone, tetramethyl-, semiquinone 
UNII-X0Q8791R69 
EINECS 208-409-8 
Duroquinone 
2,3,5,6-Tetramethylbenzo-1,4-quinone 
AI3-61045 
CHEBI:42023 
WAMKWBHYPYBEJY-UHFFFAOYSA-N 
2,3,5,6-tetramethyl-2,5-cyclohexadiene-1,4-dione 
X0Q8791R69 
2,3,5,6-tetramethyl-[1,4]benzoquinone 
Duroquinone, 97% 
tetramethylbenzoquinone 
tetramethyl benzoquinone 
527-17-3 
AC1L29BP 
AC1Q2D9M 
SCHEMBL58325 
2,5,6-Tetramethylbenzoquinone 
ACMC-209l13 
CHEMBL151604 
CTK4J6342 
ZINC87597 
DTXSID50200659 
NSC2068 
Tetramethyl-1,4-benzoquinone 
2,5,6-Tetramethyl-p-benzoquinone 
HMS1667I20 
BB_NC-00704 
NSC-2068 
p-Benzoquinone,3,5,6-tetramethyl- 
ACM527173 
ANW-31525 
BBL027347 
MFCD00001604 
STL356801 
Tetramethyl-p-benzoquinone 
2,5,6-Tetramethyl-1,4-benzoquinone 
AKOS004903738 
2,4-dione, 2,3,5,6-tetramethyl- 
DB01927 
FCH1114765 
MCULE-4663973266 
KS-0000151V 
AC-27924 
LS-56285 
M949 
Tetramethylquinone 
SC-70899 
tetramethylcyclohexa-2,5-diene-1,4-dione 
2,3,5,6-Tetramethylbenzo-1,4-quinone # 
TR-030621 
FT-0625631 
ST45022058 
p-Benzoquinone, 2,3,5,6-tetramethyl- (8CI) 
S14-1175 
2,5-Cyclohexadiene-1,4-dione,2,3,5,6-tetramethyl- 
Duroquinone, Standard for quantitative NMR, TraceCERT(R) 
2,3,5,6-tetramethylcyclohexa-2,5-diene-1,4-dione 
InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H 
D01WPJ 
C10H12O2 
CID68238 
AR-1D2127 
C10-H12-O2 
T0672 
C034257 
C511021 
53833-32-2 
2,3,5,6-Tetramethyl-1,4-benzoquinone 
DQN 
Tetramethyl-p-quinone 
Literature

Title: Genetic evidence for NAD(P)H:quinone oxidoreductase 1-catalyzed quinone reduction on passage through the mouse pulmonary circulation.

Journal: American journal of physiology. Lung cellular and molecular physiology 20110501

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Quinone-enhanced reduction of nitric oxide by xanthine/xanthine oxidase.

Journal: Chemical research in toxicology 20090501

Title: [A comparison of antioxidant properties of hypoxen and duroquinone by the method of chemiluminescence].

Journal: Biofizika 20080101

Title: Role of mitochondrial electron transport complex I in coenzyme Q1 reduction by intact pulmonary arterial endothelial cells and the effect of hyperoxia.

Journal: American journal of physiology. Lung cellular and molecular physiology 20070901

Title: Genome-wide transcriptome profiling of region-specific vulnerability to oxidative stress in the hippocampus.

Journal: Genomics 20070801

Title: The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol.

Journal: Biochemistry 20060523

Title: Exposure of spermatozoa to duroquinone may impair reproduction of the common carp (Cyprinus carpio) through oxidative stress.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20060501

Title: Influence of pulmonary arterial endothelial cells on quinone redox status: effect of hyperoxia-induced NAD(P)H:quinone oxidoreductase 1.

Journal: American journal of physiology. Lung cellular and molecular physiology 20060301

Title: Effect of chronic hyperoxic exposure on duroquinone reduction in adult rat lungs.

Journal: American journal of physiology. Lung cellular and molecular physiology 20051101

Title: Monolayers of photosystem II on gold electrodes with enhanced sensor response--effect of porosity and protein layer arrangement.

Journal: Analytical and bioanalytical chemistry 20050401

Title: Impact of pulmonary arterial endothelial cells on duroquinone redox status.

Journal: Free radical biology & medicine 20040701

Title: Evidence for two different electron transfer pathways in the same enzyme, nitrate reductase A from Escherichia coli.

Journal: European journal of biochemistry 20040601

Title: Investigation of photoinduced electron transfer in model system of vitamin E-duroquinone by time-dependent density functional theory.

Journal: The Journal of chemical physics 20040601

Title: Inactivation of mitochondrial electron transport by photosensitization of a pheophorbide a derivative.

Journal: Molecules and cells 20040430

Title: Quinone analogues regulate mitochondrial substrate competitive oxidation.

Journal: Biochemical and biophysical research communications 20040416

Title: Duroquinone reduction during passage through the pulmonary circulation.

Journal: American journal of physiology. Lung cellular and molecular physiology 20031101

Title: Interaction of exogenous quinones with membranes of higher plant chloroplasts: modulation of quinone capacities as photochemical and non-photochemical quenchers of energy in Photosystem II during light-dark transitions.

Journal: Biochimica et biophysica acta 20030605

Title: Spectrophotometric assay of yeast vitality using 2,3,5,6-tetramethyl-1,4-benzoquinone and tetrazolium salts.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030501

Title: Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.

Journal: Biochemistry 20030225

Title: Structure of the radical from one-electron oxidation of 4-hydroxycinnamate.

Journal: Free radical research 20010701

Title: Redox control of oxygen sensing in the rabbit ductus arteriosus.

Journal: The Journal of physiology 20010515

Title: The 'strict' anaerobe Desulfovibrio gigas contains a membrane-bound oxygen-reducing respiratory chain.

Journal: FEBS letters 20010504

Title: Electron transfer from heme bL to the [3Fe-4S] cluster of Escherichia coli nitrate reductase A (NarGHI).

Journal: Biochemistry 20010501

Title: Multiple activation pathways of benzene leading to products with varying genotoxic characteristics.

Journal: Environmental health perspectives 19890701

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