ContaminantDB: Quinone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2014-09-05 17:10:19 UTC

Update Date

2026-04-16 21:09:00 UTC

Accession Number

CHEM003538

Identification

Common Name

Quinone

Class

Small Molecule

Description

Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Household Toxin
Industrial/Workplace Toxin
Ketone
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Benzochinon	ChEBI
2,5-Cyclohexadiene-1,4-dione	ChEBI
Benzo-1,4-quinone	ChEBI
Benzoquinone	ChEBI
p-Benzoquinone	ChEBI
p-Chinon	ChEBI
p-Quinone	ChEBI
Para-benzoquinone	ChEBI
Chinone	Kegg
1,4-Benzoquinone	Kegg
1,4-Benzoquine	HMDB
1,4-Cyclohexadiene dioxide	HMDB
1,4-Cyclohexadienedione	HMDB
1,4-Diossibenzene	HMDB
1,4-Dioxy-benzol	HMDB
1,4-Dioxybenzene	HMDB
2,5-Cyclohexadiene-1-4-dione	HMDB
Benzo-chinon	HMDB
Chinon	HMDB
Cyclohexadiene-1,4-dione	HMDB
Cyclohexadienedione	HMDB
Eldoquin	HMDB
Para-quinone	HMDB
Quinone1,4-benzoquinone	HMDB
Semiquinone anion	HMDB
Semiquinone radicals	HMDB

Chemical Formula

C₆H₄O₂

Average Molecular Mass

108.095 g/mol

Monoisotopic Mass

108.021 g/mol

CAS Registry Number

106-51-4

IUPAC Name

cyclohexa-2,5-diene-1,4-dione

Traditional Name

quinone

SMILES

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

InChI Identifier

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

InChI Key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

benzoquinone (CHEBI:16509 )
a small molecule (P-BENZOQUINONE )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Bone Marrow
Fibroblasts
Kidney
Liver
Neuron
Skeletal Muscle

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	115.7 °C
Boiling Point	Sublimes
Solubility	11.1 mg/mL at 18 °C

Predicted Properties

Property	Value	Source
Water Solubility	45.4 g/L	ALOGPS
logP	0.21	ALOGPS
logP	1.02	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.03 m³·mol⁻¹	ChemAxon
Polarizability	9.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-1900000000-9b99afb0e9c6350434a4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-1900000000-9b99afb0e9c6350434a4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9500000000-6664b553a87d4fc15f94	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-7900000000-fca2433f986ba378f8c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00or-9000000000-6897ef153b4119e50ceb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014u-9000000000-9bddbff45c6d0d3e0cf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 7V, negative	splash10-014i-1900000000-6d13549d8c534563dc9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 9V, negative	splash10-014i-1900000000-af62dc0334e009fe3e5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 14V, negative	splash10-014i-3900000000-1167cf77177c0761168e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d886efcfed5b0135bcd5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-7f5c75e048ee2f454e33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9100000000-db1ffa9cf092dd5e4551	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-0f04c7bee6397237ee21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-2c6cb60a5040c6239920	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-f1f9c8ded0fe97bb684d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3c2c54b9382bddbdf0df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-62ea0dd9303aae554ccd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-7966cc06756dd3b8c736	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-28217a7272677bec662a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zgi-9200000000-8777cde0dbcbb2157cdd	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Quinone is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (19)

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0003364

FooDB ID

FDB005755

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

P-BENZOQUINONE

METLIN ID

6905

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Harman, Robert E.; Cason, James. The preparation of quinones from p-aminophenols obtained by electrolytic reduction of aromatic nitro compounds. Journal of Organic Chemistry (1952), 17 1058-62.

MSDS

Link

General References

1. Harman, Robert E.; Cason, James. The preparation of quinones from p-aminophenols obtained by electrolytic reduction of aromatic nitro compounds. Journal of Organic Chemistry (1952), 17 1058-62.

2. Harman, Robert E.; Cason, James. The preparation of quinones from p-aminophenols obtained by electrolytic reduction of aromatic nitro compounds. Journal of Organic Chemistry (1952), 17 1058-62.

3. Gaskell M, McLuckie KI, Farmer PB: Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Carcinogenesis. 2005 Mar;26(3):673-80. Epub 2004 Dec 23.

4. Fabiani R, De Bartolomeo A, Morozzi G: Involvement of oxygen free radicals in the serum-mediated increase of benzoquinone genotoxicity. Environ Mol Mutagen. 2005 Oct;46(3):156-63.

5. Bello RI, Gomez-Diaz C, Navarro F, Alcain FJ, Villalba JM: Expression of NAD(P)H:quinone oxidoreductase 1 in HeLa cells: role of hydrogen peroxide and growth phase. J Biol Chem. 2001 Nov 30;276(48):44379-84. Epub 2001 Sep 20.

6. Park S, Geddes TJ, Javitch JA, Kuhn DM: Dopamine prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide: is nitrotyrosine formation an early step in dopamine neuronal damage? J Biol Chem. 2003 Aug 1;278(31):28736-42. Epub 2003 May 27.

7. Siegel D, Ryder J, Ross D: NAD(P)H: quinone oxidoreductase 1 expression in human bone marrow endothelial cells. Toxicol Lett. 2001 Dec 15;125(1-3):93-8.

8. Roberg K, Johansson U, Ollinger K: Lysosomal release of cathepsin D precedes relocation of cytochrome c and loss of mitochondrial transmembrane potential during apoptosis induced by oxidative stress. Free Radic Biol Med. 1999 Dec;27(11-12):1228-37.

9. Kwasnicka-Crawford DA, Vincent SR: Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Biochem Biophys Res Commun. 2005 Oct 21;336(2):565-71.