U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Identification of zeta-crystallin/NADPH:quinone reductase as a renal glutaminase mRNA pH response element-binding protein.
2001-06-15
Retention of heme in axial ligand mutants of succinate-ubiquinone xxidoreductase (complex II) from Escherichia coli.
2001-06-01
Reproducibility of toxicity across mode of toxic action in the Tetrahymena population growth impairment assay.
2001-06
The Quinone-binding sites of the Saccharomyces cerevisiae succinate-ubiquinone oxidoreductase.
2001-05-18
Role of sodium bioenergetics in Vibrio cholerae.
2001-05-01
Na(+) translocation by bacterial NADH:quinone oxidoreductases: an extension to the complex-I family of primary redox pumps.
2001-05-01
Recent progress in the Na(+)-translocating NADH-quinone reductase from the marine Vibrio alginolyticus.
2001-05-01
The antioxidant enzyme quinone reductase is up-regulated in vivo following cerebral ischemia.
2001-04-17
The role of glutathione reductase in the cytotoxicity of chromium (VI) in isolated rat hepatocytes.
2001-04-16
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.
2001-04-15
Factors influencing the induction of DT-diaphorase activity by 1,2-dithiole-3-thione in human tumor cell lines.
2001-04-15
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.
2001-04-12
Insight into the chemistry of flavin reduction and oxidation in Escherichia coli dihydroorotate dehydrogenase obtained by rapid reaction studies.
2001-04-10
Iron coordination in photosystem II: interaction between bicarbonate and the QB pocket studied by Fourier transform infrared spectroscopy.
2001-04-03
Structure-activity study on the quinone/quinone methide chemistry of flavonoids.
2001-04
Subfractionation, characterization and photooxidation of crude oil resins.
2001-04
Heritable variation in quinone-induced haustorium development in the parasitic plant Triphysaria.
2001-04
Copper neurotoxicity is dependent on dopamine-mediated copper uptake and one-electron reduction of aminochrome in a rat substantia nigra neuronal cell line.
2001-04
[Polymorphism of MAO-B gene and NAD(P)H: quinone oxidoreductase gene in Parkinson's disease].
2001-04
Oxidative damage and direct adducts in calf thymus DNA induced by the pentachlorophenol metabolites, tetrachlorohydroquinone and tetrachloro-1,4-benzoquinone.
2001-04
Modulation of primary radical pair kinetics and energetics in photosystem II by the redox state of the quinone electron acceptor Q(A).
2001-04
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.
2001-04
Photodynamic therapy with hypericin in a mouse P388 tumor model: vascular effects determine the efficacy.
2001-04
Effects of peroxisome proliferators on antioxidant enzymes and antioxidant vitamins in rats and hamsters.
2001-04
Temporary inactivation of plasma amine oxidase by alkylhydrazines. A combined enzyme/model study implicates cofactor reduction/reoxidation but cofactor deoxygenation and subsequent reoxygenation in the case of hydrazine itself.
2001-03-23
Dopamine induced protein damage in mitochondrial-synaptosomal fraction of rat brain.
2001-03-23
Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.
2001-03-14
Trapping conformational intermediate states in the reaction center protein from photosynthetic bacteria.
2001-03-13
NAD/NADH models with axial/central chiralities: superiority of the quinoline ring system.
2001-03-09
Hydrophobicity of the NADPH binding domain of camel lens zeta-crystallin.
2001-03-09
Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN.
2001-03-09
Development of non-radio isotopic endpoint of murine local lymph node assay based on 5-bromo-2'-deoxyuridine (BrdU) incorporation.
2001-03-08
Absorption changes induced by the binding of triazines to the QB pocket in reaction centers of Rhodobacter capsulatus.
2001-03-06
Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids.
2001-03-02
[Coenzyme Q and its therapeutic use].
2001-03
Electroanalytical exploitation of quinone-thiol interactions: application to the selective determination of cysteine.
2001-03
The use of bioluminescent biotests for study of natural and laboratory aquatic ecosystems.
2001-03
Preferential expression of antioxidant response element mediated gene expression in astrocytes.
2001-03
Generalized approach to the regulation and integration of gene expression.
2001-03
The 1:1 adduct of 2,5-dihydroxy-1,4-benzoquinone with 4,4'-bipyridine.
2001-03
A third crystal form of Wolinella succinogenes quinol:fumarate reductase reveals domain closure at the site of fumarate reduction.
2001-03
Synthesis, crystal structure, spectral studies, and catechol oxidase activity of trigonal bipyramidal Cu(II) complexes derived from a tetradentate diamide bisbenzimidazole ligand.
2001-02-26
Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes.
2001-02-23
Induction of human NAD(P)H:quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin.
2001-02-03
Synthesis of a new polycyclic quinone by reduction of a dihydrobenz.
2001-02
Effects of a water-soluble extract of rosemary and its purified component rosmarinic acid on xenobiotic-metabolizing enzymes in rat liver.
2001-02
Proteolytic activation of latent Paraguaya peach PPO. Characterization of monophenolase activity.
2001-02
Quinone oxidoreductase message levels are differentially regulated in parasitic and non-parasitic plants exposed to allelopathic quinones.
2001-02
Membrane bioenergetics and virulence: problems and prospects.
2001-01
Hormones and cancer 2000.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:37:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:37:15 GMT 2025
Record UNII
3T006GV98U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Quinone
MI   WHO-DD  
Common Name English
1,4-BENZOQUINONE
HSDB   USP-RS  
Preferred 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
Quinone [WHO-DD]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 59805
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
NCI_THESAURUS C796
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
Code System Code Type Description
SMS_ID
100000151727
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
DAILYMED
3T006GV98U
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-405-2
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
MERCK INDEX
m9461
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1056504
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
FDA UNII
3T006GV98U
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
CAS
106-51-4
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
WIKIPEDIA
1,4-BENZOQUINONE
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
CHEBI
36141
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID6020145
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
NSC
36324
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
HSDB
1111
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
NCI_THESAURUS
C95317
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
PUBCHEM
4650
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
RXCUI
319868
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY RxNorm
CHEBI
16509
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
EVMPD
SUB126217
Created by admin on Mon Mar 31 18:37:15 GMT 2025 , Edited by admin on Mon Mar 31 18:37:15 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY