| Record Information |
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| Version | 2.0 |
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| Creation Date | 2014-09-05 17:10:19 UTC |
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| Update Date | 2014-12-24 20:26:52 UTC |
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| Accession Number | T3D4578 |
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| Identification |
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| Common Name | Quinone |
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| Class | Small Molecule |
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| 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. |
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| Compound Type | - Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Ketone
- Metabolite
- Organic Compound
- Pollutant
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 1,4-Benzoquine | | 1,4-Benzoquinone | | 1,4-Cyclohexadiene dioxide | | 1,4-Cyclohexadienedione | | 1,4-Diossibenzene | | 1,4-Dioxy-benzol | | 1,4-Dioxybenzene | | 2,5-Cyclohexadiene-1,4-dione | | 2,5-cyclohexadiene-1-4-dione | | Benzo-1,4-quinone | | Benzo-chinon | | Benzoquinone | | Chinon | | Chinone | | Cyclohexadiene-1,4-dione | | Cyclohexadienedione | | Eldoquin | | p-Benzoquinone | | p-Chinon | | p-Quinone | | Para-Benzoquinone | | Para-Quinone | | Quinone1,4-Benzoquinone | | Semiquinone anion | | Semiquinone radicals |
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| Chemical Formula | C6H4O2 |
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| Average Molecular Mass | 108.095 g/mol |
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| Monoisotopic Mass | 108.021 g/mol |
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| CAS Registry Number | 106-51-4 |
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| IUPAC Name | cyclohexa-2,5-diene-1,4-dione |
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| Traditional Name | quinone |
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| SMILES | O=C1C=CC(=O)C=C1 |
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| InChI Identifier | InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H |
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| InChI Key | InChIKey=AZQWKYJCGOJGHM-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbonyl compounds |
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| Direct Parent | P-benzoquinones |
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| Alternative Parents | |
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| Substituents | - P-benzoquinone
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | - Bone Marrow
- Fibroblasts
- Kidney
- Liver
- Neuron
- Skeletal Muscle
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 115.7 °C | | Boiling Point | Sublimes | | Solubility | 11.1 mg/mL at 18 °C | | LogP | 0.2 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0zgi-9500000000-c8bfbbc465fad7929f87 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00xr-1900000000-9b99afb0e9c6350434a4 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0zgi-9500000000-c8bfbbc465fad7929f87 | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00xr-1900000000-9b99afb0e9c6350434a4 | 2018-05-18 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9500000000-6664b553a87d4fc15f94 | 2016-09-22 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-7900000000-fca2433f986ba378f8c9 | 2012-07-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00or-9000000000-6897ef153b4119e50ceb | 2012-07-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014u-9000000000-9bddbff45c6d0d3e0cf1 | 2012-07-25 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0zgi-9500000000-c8bfbbc465fad7929f87 | 2012-08-31 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-QFT 7V, negative | splash10-014i-1900000000-6d13549d8c534563dc9b | 2020-07-21 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-QFT 9V, negative | splash10-014i-1900000000-af62dc0334e009fe3e5b | 2020-07-21 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-QFT 14V, negative | splash10-014i-3900000000-1167cf77177c0761168e | 2020-07-21 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-d886efcfed5b0135bcd5 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-1900000000-7f5c75e048ee2f454e33 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9100000000-db1ffa9cf092dd5e4551 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-648d78080240a1294e4c | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-648d78080240a1294e4c | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-5900000000-0f04c7bee6397237ee21 | 2016-09-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-2c6cb60a5040c6239920 | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-4900000000-f1f9c8ded0fe97bb684d | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-3c2c54b9382bddbdf0df | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-62ea0dd9303aae554ccd | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2900000000-7966cc06756dd3b8c736 | 2021-09-24 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-28217a7272677bec662a | 2021-09-24 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0zgi-9200000000-8777cde0dbcbb2157cdd | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | 2012-12-05 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-25 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental) | Not Available | 2012-12-05 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| 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. |
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| 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. |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (20) |
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| Uses/Sources | This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation. |
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| Minimum Risk Level | Not Available |
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| 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. |
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| 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. |
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| 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. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03364 |
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| PubChem Compound ID | 4650 |
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| ChEMBL ID | CHEMBL8320 |
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| ChemSpider ID | 4489 |
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| KEGG ID | C00472 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 16509 |
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| BioCyc ID | CPD-8130 |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | PLQ |
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| ACToR ID | Not Available |
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| Wikipedia Link | Quinone |
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| References |
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| 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. |
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| MSDS | Link |
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| General References | - 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. [15618234 ]
- 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. [15920754 ]
- 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. [11567026 ]
- 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. [12771134 ]
- 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. [11701227 ]
- 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. [10641715 ]
- 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. [16140270 ]
- Yamazaki H, Shibata A, Suzuki M, Nakajima M, Shimada N, Guengerich FP, Yokoi T: Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-450 2C8 and P-450 3A4 in human liver microsomes. Drug Metab Dispos. 1999 Nov;27(11):1260-6. [10534310 ]
- He K, Woolf TF, Kindt EK, Fielder AE, Talaat RE: Troglitazone quinone formation catalyzed by human and rat CYP3A: an atypical CYP oxidation reaction. Biochem Pharmacol. 2001 Jul 15;62(2):191-8. [11389877 ]
- Soucek P: Cytochrome P450 destruction by quinones: comparison of effects in rat and human liver microsomes. Chem Biol Interact. 1999 Aug 1;121(3):223-36. [10462055 ]
- Xu L, Eiseman JL, Egorin MJ, D'Argenio DZ: Physiologically-based pharmacokinetics and molecular pharmacodynamics of 17-(allylamino)-17-demethoxygeldanamycin and its active metabolite in tumor-bearing mice. J Pharmacokinet Pharmacodyn. 2003 Jun;30(3):185-219. [14571691 ]
- He K, Talaat RE, Woolf TF: Incorporation of an oxygen from water into troglitazone quinone by cytochrome P450 and myeloperoxidase. Drug Metab Dispos. 2004 Apr;32(4):442-6. [15039298 ]
- Toyota T, Ueno Y: [Clinical effect and side effect of troglitazone]. Nihon Rinsho. 2000 Feb;58(2):376-82. [10707561 ]
- Smith MT: The mechanism of benzene-induced leukemia: a hypothesis and speculations on the causes of leukemia. Environ Health Perspect. 1996 Dec;104 Suppl 6:1219-25. [9118896 ]
- Terman A, Neuzil J, Kagedal K, Ollinger K, Brunk UT: Decreased apoptotic response of inclusion-cell disease fibroblasts: a consequence of lysosomal enzyme missorting? Exp Cell Res. 2002 Mar 10;274(1):9-15. [11855852 ]
- Mu D, Medzihradszky KF, Adams GW, Mayer P, Hines WM, Burlingame AL, Smith AJ, Cai D, Klinman JP: Primary structures for a mammalian cellular and serum copper amine oxidase. J Biol Chem. 1994 Apr 1;269(13):9926-32. [8144587 ]
- Hasegawa T, Matsuzaki M, Takeda A, Kikuchi A, Furukawa K, Shibahara S, Itoyama Y: Increased dopamine and its metabolites in SH-SY5Y neuroblastoma cells that express tyrosinase. J Neurochem. 2003 Oct;87(2):470-5. [14511124 ]
- Lin YS, Vermeulen R, Tsai CH, Waidyanatha S, Lan Q, Rothman N, Smith MT, Zhang L, Shen M, Li G, Yin S, Kim S, Rappaport SM: Albumin adducts of electrophilic benzene metabolites in benzene-exposed and control workers. Environ Health Perspect. 2007 Jan;115(1):28-34. [17366815 ]
- Halliwell, Barry B., and Henrik E. Poulsen (2006). Cigarette Smoke and Oxidative Stress. Berlin: Springer. [ISBN: 978-3-540-31410-3 (Print) 978-3-540-32232-0 (Online)]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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