Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:10 UTC |
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HMDB ID | HMDB0001505 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Benzene |
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Description | Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene, also known as benzol or [6]annulene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene is a natural constituent of crude oil and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. It is sometimes abbreviated PhH. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma around petrol (gasoline) stations. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although a major industrial chemical, benzene finds limited use in consumer items because of its toxicity. Benzene is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Benzene has been found to be associated with several diseases such as autism and pervasive developmental disorder not otherwise specified. |
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Structure | InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H |
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Synonyms | Value | Source |
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[6]Annulene | ChEBI | Benzen | ChEBI | Benzine | ChEBI | Benzol | ChEBI | Benzole | ChEBI | Bicarburet OF hydrogen | ChEBI | Coal naphtha | ChEBI | Cyclohexatriene | ChEBI | Mineral naphtha | ChEBI | Phene | ChEBI | Phenyl hydride | ChEBI | Pyrobenzol | ChEBI | Pyrobenzole | ChEBI | (6)Annulene | HMDB | Annulene | HMDB | Aromatic alkane | HMDB | Benzeen | HMDB | Benzin | HMDB | Benzinum | HMDB | Benzol 90 | HMDB | Benzolene | HMDB | Benzolo | HMDB | Benzolum | HMDB | BNZ | HMDB | Carbon oil | HMDB | Fenzen | HMDB | Motor benzol | HMDB | Polystream | HMDB | RNG | HMDB | {[6]annulene} | HMDB |
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Chemical Formula | C6H6 |
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Average Molecular Weight | 78.1118 |
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Monoisotopic Molecular Weight | 78.046950192 |
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IUPAC Name | benzene |
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Traditional Name | benzene |
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CAS Registry Number | 71-43-2 |
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SMILES | C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H |
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InChI Key | UHOVQNZJYSORNB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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Substituents | - Monocyclic benzene moiety
- Aromatic hydrocarbon
- Unsaturated hydrocarbon
- Hydrocarbon
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 5.5 °C | Not Available | Boiling Point | 80.00 to 81.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 1.79 mg/mL | Not Available | LogP | 2.13 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-004i-9000000000-70967112fec69784847c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-004i-9000000000-92ccc664b07cb6c56de9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene CI-B (Non-derivatized) | splash10-004i-9100000000-11f8463e7c6286637b1b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-004i-9000000000-70967112fec69784847c | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-004i-9000000000-92ccc664b07cb6c56de9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene EI-B (Non-derivatized) | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzene CI-B (Non-derivatized) | splash10-004i-9100000000-11f8463e7c6286637b1b | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzene GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-9000000000-c5901591488019f3ac5d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzene GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-004i-9000000000-08f396d6cb4660e57caa | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzene EI-B (HITACHI RMU-7M) , Positive-QTOF | splash10-004i-9000000000-70967112fec69784847c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzene EI-B (JEOL JMS-D-3000) , Positive-QTOF | splash10-004i-9000000000-92ccc664b07cb6c56de9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzene EI-B (HP 5970) , Positive-QTOF | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzene CI-B (FINNIGAN-MAT 4500) , Positive-QTOF | splash10-004i-9100000000-11f8463e7c6286637b1b | 2012-08-31 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 10V, Positive-QTOF | splash10-004i-9000000000-45ac36cbb443a00d6a17 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 20V, Positive-QTOF | splash10-004i-9000000000-9cad19d98e6420c7b6a3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 40V, Positive-QTOF | splash10-004i-9000000000-2dace4807cb04a7942de | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 10V, Negative-QTOF | splash10-004i-9000000000-b9df9bb9660e1fc49a7f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 20V, Negative-QTOF | splash10-004i-9000000000-b9df9bb9660e1fc49a7f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 40V, Negative-QTOF | splash10-004i-9000000000-b4ff542394722302be43 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 10V, Negative-QTOF | splash10-004i-9000000000-fc58e0949de9ca4842ff | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 20V, Negative-QTOF | splash10-004i-9000000000-fc58e0949de9ca4842ff | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 40V, Negative-QTOF | splash10-004i-9000000000-fc58e0949de9ca4842ff | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 10V, Positive-QTOF | splash10-004i-9000000000-b961755486c61c33c1c7 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 20V, Positive-QTOF | splash10-0fb9-9000000000-9a8a4f7775597a0e167e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzene 40V, Positive-QTOF | splash10-004i-9000000000-fd85b2b474c37c371a5a | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Breath
- Feces
- Saliva
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Tissue Locations | - Bone Marrow
- Epidermis
- Leukocyte
- Liver
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.000384 (0.000320-0.000448) uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.000307 (0.000256-0.000384) uM | Children (1-13 years old) | Not Specified | Normal | | details | Breath | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) non progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Autism | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Pervasive Developmental Disorder Not Otherwise Specified | | details | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Celiac disease | | details |
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Associated Disorders and Diseases |
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Disease References | Autism |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Pervasive developmental disorder not otherwise specified |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Celiac disease |
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- Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012843 |
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KNApSAcK ID | C00033435 |
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Chemspider ID | 236 |
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KEGG Compound ID | C01407 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Benzene |
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METLIN ID | 6285 |
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PubChem Compound | 241 |
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PDB ID | Not Available |
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ChEBI ID | 16716 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1221761 |
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References |
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Synthesis Reference | Copisarow, Maurice; Long, Cyril N H. The Friedel-Crafts' reaction. II. Migration of halogen atoms in the benzene nucleus. Journal of the Chemical Society, Transactions (1921), 119 442-7. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Wiwanitkit V, Soogarun S, Suwansaksri J: Urine phenol and myeloperoxidase index: an observation in benzene exposed subjects. Leuk Lymphoma. 2004 Aug;45(8):1643-5. [PubMed:15370219 ]
- Wang S, Chen H, Wang X: [Studies on relationship between exposure to low concentration of mixed benzene and lower quality of semen and very early fetal loss]. Zhonghua Yu Fang Yi Xue Za Zhi. 2000 Sep;34(5):271-3. [PubMed:11372393 ]
- Zhang L, Wang Y, Shang N, Smith MT: Benzene metabolites induce the loss and long arm deletion of chromosomes 5 and 7 in human lymphocytes. Leuk Res. 1998 Feb;22(2):105-13. [PubMed:9593466 ]
- 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. [PubMed:15920754 ]
- Turteltaub KW, Mani C: Benzene metabolism in rodents at doses relevant to human exposure from urban air. Res Rep Health Eff Inst. 2003 Feb;(113):1-26; discussion 27-35. [PubMed:12675491 ]
- Irons RD, Stillman WS: Impact of benzene metabolites on differentiation of bone marrow progenitor cells. Environ Health Perspect. 1996 Dec;104 Suppl 6:1247-50. [PubMed:9118900 ]
- Rothman N, Li GL, Dosemeci M, Bechtold WE, Marti GE, Wang YZ, Linet M, Xi LQ, Lu W, Smith MT, Titenko-Holland N, Zhang LP, Blot W, Yin SN, Hayes RB: Hematotoxicity among Chinese workers heavily exposed to benzene. Am J Ind Med. 1996 Mar;29(3):236-46. [PubMed:8833776 ]
- Barbera N, Bulla G, Romano G: A fatal case of benzene poisoning. J Forensic Sci. 1998 Nov;43(6):1250-1. [PubMed:9846407 ]
- Rolle-Kampczyk UE, Rehwagen M, Franck U, Weiss H, Krumbiegel P, Herbarth O: Bio-effect monitoring using a [(15)N]methacetin test as diagnostic tool to monitor remediation effects in an industrially polluted region. Toxicol Lett. 2006 Apr 10;162(2-3):234-8. Epub 2005 Oct 19. [PubMed:16242870 ]
- Vermeulen R, Lan Q, Zhang L, Gunn L, McCarthy D, Woodbury RL, McGuire M, Podust VN, Li G, Chatterjee N, Mu R, Yin S, Rothman N, Smith MT: Decreased levels of CXC-chemokines in serum of benzene-exposed workers identified by array-based proteomics. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17041-6. Epub 2005 Nov 14. [PubMed:16286641 ]
- Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Drug Metab Dispos. 1999 Dec;27(12):1499-504. [PubMed:10570033 ]
- Gut I, Nedelcheva V, Soucek P, Stopka P, Tichavska B: Cytochromes P450 in benzene metabolism and involvement of their metabolites and reactive oxygen species in toxicity. Environ Health Perspect. 1996 Dec;104 Suppl 6:1211-8. [PubMed:9118895 ]
- Irons RD, Lv L, Gross SA, Ye X, Bao L, Wang XQ, Ryder J, Armstrong TW, Zhou Y, Miao L, Le AT, Kerzic PJ, Ni W, Fu H: Chronic exposure to benzene results in a unique form of dysplasia. Leuk Res. 2005 Dec;29(12):1371-80. Epub 2005 Sep 23. [PubMed:16183116 ]
- Xiao G, Pan C, Cai Y, Lin H, Fu Z: Effect of benzene, toluene, xylene on the semen quality and the function of accessory gonad of exposed workers. Ind Health. 2001 Apr;39(2):206-10. [PubMed:11341554 ]
- Dees C, Askari M, Henley D: Carcinogenic potential of benzene and toluene when evaluated using cyclin-dependent kinase activation and p53-DNA binding. Environ Health Perspect. 1996 Dec;104 Suppl 6:1289-92. [PubMed:9118908 ]
- Ward E, Hornung R, Morris J, Rinsky R, Wild D, Halperin W, Guthrie W: Risk of low red or white blood cell count related to estimated benzene exposure in a rubberworker cohort (1940-1975) Am J Ind Med. 1996 Mar;29(3):247-57. [PubMed:8833777 ]
- Seaton MJ, Schlosser P, Medinsky MA: In vitro conjugation of benzene metabolites by human liver: potential influence of interindividual variability on benzene toxicity. Carcinogenesis. 1995 Jul;16(7):1519-27. [PubMed:7614685 ]
- Brugnone F, Perbellini L, Romeo L, Cerpelloni M, Bianchin M, Tonello A: Benzene in blood as a biomarker of low level occupational exposure. Sci Total Environ. 1999 Sep 1;235(1-3):247-52. [PubMed:10535123 ]
- Ress NB: NTP Technical Report on the metabolism, toxicity and predicted carcinogenicity of diazoaminobenzene (CAS No. 136-35-6). Toxic Rep Ser. 2002 Sep;(73):1-23, A1-C6. [PubMed:12370695 ]
- Surralles J, Autio K, Nylund L, Jarventaus H, Norppa H, Veidebaum T, Sorsa M, Peltonen K: Molecular cytogenetic analysis of buccal cells and lymphocytes from benzene-exposed workers. Carcinogenesis. 1997 Apr;18(4):817-23. [PubMed:9111220 ]
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