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Record Information |
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Version | 4.0 |
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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 | 2020-04-22 23:33:09 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, 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 possibly neutral. Benzene exists in all living organisms, ranging from bacteria to humans. Outside of the human body, benzene is found, on average, in the highest concentration in safflowers. benzene has also been detected, but not quantified in, a few different foods, such as common beans, guava, and lovages. This could make benzene a potential biomarker for the consumption of these foods. 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; also benzene has been linked to the inborn metabolic disorders including celiac disease. |
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Structure | |
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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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Physiological effect | Health effect: |
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Disposition | Source: Route of exposure: Biological location: |
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Role | Indirect biological role: Environmental role: Industrial application: |
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Physical Properties |
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State | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 5.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1.79 mg/mL | Not Available | LogP | 2.13 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-70967112fec69784847c | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-92ccc664b07cb6c56de9 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-004i-9100000000-11f8463e7c6286637b1b | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-70967112fec69784847c | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004i-9000000000-92ccc664b07cb6c56de9 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-004i-9100000000-11f8463e7c6286637b1b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-9000000000-c5901591488019f3ac5d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-004i-9000000000-70967112fec69784847c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-004i-9000000000-92ccc664b07cb6c56de9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HP 5970) , Positive | splash10-0fb9-9000000000-2aae37aac9f2a02d5e8b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positive | splash10-004i-9100000000-11f8463e7c6286637b1b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-45ac36cbb443a00d6a17 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9000000000-9cad19d98e6420c7b6a3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-2dace4807cb04a7942de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-b9df9bb9660e1fc49a7f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-b9df9bb9660e1fc49a7f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-b4ff542394722302be43 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-004i-9000000000-08f396d6cb4660e57caa | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | 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 | Not Available |
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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 | |
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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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