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Details

Stereochemistry ACHIRAL
Molecular Formula C6H4O2
Molecular Weight 108.0948
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINONE

SMILES

O=C1C=CC(=O)C=C1

InChI

InChIKey=AZQWKYJCGOJGHM-UHFFFAOYSA-N
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H

HIDE SMILES / InChI

Molecular Formula C6H4O2
Molecular Weight 108.0948
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Quinone is extensively used as a chemical intermediate, a polymerization inhibitor, an oxidizing agent, a photographic chemical, a tanning agent, and a chemical reagent. Quinone (p-benzoquinone) was first produced commercially in 1919 and has since been manufactured in several European countries. Its major use is in hydroquinone production, but it is also used as a polymerization inhibitor and as an intermediate in the production of a variety of substances, including rubber accelerators and oxidizing agents. It is used in the dye, textile, chemical, tanning, and cosmetic industries. In chemical synthesis for hydroquinone and other chemicals, quinone is used as an intermediate. It is also used in the manufacturing industries and chemical laboratory associated with protein fibre, photographic film, hydrogen peroxide, and gelatin making. Occupational exposure to quinone may occur in the dye, textile, chemical, tanning, and cosmetic industries. Inhalation exposure to quinone may occur from tobacco smoke. Quinone is a major metabolite of benzene. It has been found to generate H2O2 in cells. It has been suggested that the peroxide reacts with Cu(I) to produce an active species that induces internucleosomal DNA fragmentation.

Approval Year

PubMed

PubMed

TitleDatePubMed
Hormones and cancer 2000.
2001
Structure-activity study on the quinone/quinone methide chemistry of flavonoids.
2001 Apr
Heritable variation in quinone-induced haustorium development in the parasitic plant Triphysaria.
2001 Apr
[Polymorphism of MAO-B gene and NAD(P)H: quinone oxidoreductase gene in Parkinson's disease].
2001 Apr
Modulation of primary radical pair kinetics and energetics in photosystem II by the redox state of the quinone electron acceptor Q(A).
2001 Apr
Base sequence-specific attack of stilbene estrogen metabolite(s) on the mitochondrial DNA: implications in the induction of instability in the mitochondrial genome in the kidney of Syrian hamsters.
2001 Apr
Photodynamic therapy with hypericin in a mouse P388 tumor model: vascular effects determine the efficacy.
2001 Apr
Effects of peroxisome proliferators on antioxidant enzymes and antioxidant vitamins in rats and hamsters.
2001 Apr
Insight into the chemistry of flavin reduction and oxidation in Escherichia coli dihydroorotate dehydrogenase obtained by rapid reaction studies.
2001 Apr 10
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
2001 Apr 12
The Cap'n'Collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes.
2001 Apr 15
Factors influencing the induction of DT-diaphorase activity by 1,2-dithiole-3-thione in human tumor cell lines.
2001 Apr 15
The role of glutathione reductase in the cytotoxicity of chromium (VI) in isolated rat hepatocytes.
2001 Apr 16
The antioxidant enzyme quinone reductase is up-regulated in vivo following cerebral ischemia.
2001 Apr 17
Plasma membrane electron transport coupled to Na(+) extrusion in the halotolerant alga Dunaliella.
2001 Apr 2
Efficient large scale purification of his-tagged proton translocating NADH:ubiquinone oxidoreductase (complex I) from the strictly aerobic yeast Yarrowia lipolytica.
2001 Apr 2
Transmembrane orientation and topology of the NADH:quinone oxidoreductase putative quinone binding subunit NuoH.
2001 Apr 2
Long-lived charge-separated states in bacterial reaction centers isolated from Rhodobacter sphaeroides.
2001 Apr 2
Evidence for a quinone binding site close to the interface between NUOD and NUOB subunits of Complex I.
2001 Apr 2
Quinone oxidoreductase message levels are differentially regulated in parasitic and non-parasitic plants exposed to allelopathic quinones.
2001 Feb
Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes.
2001 Feb 23
Synthesis, crystal structure, spectral studies, and catechol oxidase activity of trigonal bipyramidal Cu(II) complexes derived from a tetradentate diamide bisbenzimidazole ligand.
2001 Feb 26
Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin.
2001 Feb 3
Rate constants in two dimensions of electron transfer between pyruvate oxidase, a membrane enzyme, and ubiquinone (coenzyme Q8), its water-insoluble electron carrier.
2001 Feb 6
Effects of extraction of the H-subunit from Rhodobacter sphaeroides reaction centers on relaxation processes associated with charge separation.
2001 Jan
Formation of nitric oxide from nitroxyl anion: role of quinones and ferricytochrome c.
2001 Jan
Thiols can either enhance or suppress DNA damage induction by catecholestrogens.
2001 Jan 1
FMN is covalently attached to a threonine residue in the NqrB and NqrC subunits of Na(+)-translocating NADH-quinone reductase from Vibrio alginolyticus.
2001 Jan 12
Reproducibility of toxicity across mode of toxic action in the Tetrahymena population growth impairment assay.
2001 Jun
Retention of heme in axial ligand mutants of succinate-ubiquinone xxidoreductase (complex II) from Escherichia coli.
2001 Jun 1
Identification of zeta-crystallin/NADPH:quinone reductase as a renal glutaminase mRNA pH response element-binding protein.
2001 Jun 15
[Coenzyme Q and its therapeutic use].
2001 Mar
The use of bioluminescent biotests for study of natural and laboratory aquatic ecosystems.
2001 Mar
Preferential expression of antioxidant response element mediated gene expression in astrocytes.
2001 Mar
Generalized approach to the regulation and integration of gene expression.
2001 Mar
The 1:1 adduct of 2,5-dihydroxy-1,4-benzoquinone with 4,4'-bipyridine.
2001 Mar
A third crystal form of Wolinella succinogenes quinol:fumarate reductase reveals domain closure at the site of fumarate reduction.
2001 Mar
Incorporation of plastoquinone and ubiquinone into liposome membranes studied by HPLC analysis. The effect of side chain length and redox state of quinone.
2001 Mar
Reactive oxygen species from NAD(P)H:quinone oxidoreductase constitutively activate NF-kappaB in malignant melanoma cells.
2001 Mar
Low NAD(P)H:quinone oxidoreductase 1 activity is associated with increased risk of acute leukemia in adults.
2001 Mar 1
Trapping conformational intermediate states in the reaction center protein from photosynthetic bacteria.
2001 Mar 13
Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.
2001 Mar 14
Dopamine induced protein damage in mitochondrial-synaptosomal fraction of rat brain.
2001 Mar 23
Absorption changes induced by the binding of triazines to the QB pocket in reaction centers of Rhodobacter capsulatus.
2001 Mar 6
Development of non-radio isotopic endpoint of murine local lymph node assay based on 5-bromo-2'-deoxyuridine (BrdU) incorporation.
2001 Mar 8
Hydrophobicity of the NADPH binding domain of camel lens zeta-crystallin.
2001 Mar 9
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.
2001 Mar 9
Role of sodium bioenergetics in Vibrio cholerae.
2001 May 1
Na(+) translocation by bacterial NADH:quinone oxidoreductases: an extension to the complex-I family of primary redox pumps.
2001 May 1
Recent progress in the Na(+)-translocating NADH-quinone reductase from the marine Vibrio alginolyticus.
2001 May 1
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:50:58 GMT 2023
Edited
by admin
on Fri Dec 15 16:50:58 GMT 2023
Record UNII
3T006GV98U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINONE
MI   WHO-DD  
Common Name English
NSC-36324
Code English
1,4-BENZOQUINONE [HSDB]
Common Name English
PARABENZOCHINON
Common Name English
P-BENZOQUINONE
Common Name English
PARA-QUINONE [IARC]
Common Name English
1,4-BENZOQUINONE [USP-RS]
Common Name English
QUINONE [MI]
Common Name English
PARA-BENZOQUINONE
Systematic Name English
2,5-CYCLOHEXADIENE-1,4-DIONE
Systematic Name English
PARA-QUINONE
Common Name English
1,4-BENZOQUINONE
HSDB   USP-RS  
Systematic Name English
Quinone [WHO-DD]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 59805
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
NCI_THESAURUS C796
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
Code System Code Type Description
SMS_ID
100000151727
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
DAILYMED
3T006GV98U
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-405-2
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
MERCK INDEX
m9461
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1056504
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
FDA UNII
3T006GV98U
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
CAS
106-51-4
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
WIKIPEDIA
1,4-BENZOQUINONE
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
CHEBI
36141
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID6020145
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
NSC
36324
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
HSDB
1111
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
NCI_THESAURUS
C95317
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
PUBCHEM
4650
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
RXCUI
319868
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY RxNorm
CHEBI
16509
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
EVMPD
SUB126217
Created by admin on Fri Dec 15 16:50:58 GMT 2023 , Edited by admin on Fri Dec 15 16:50:58 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY