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Showing metabocard for Benzene (HMDB0001505)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:26 UTC
HMDB IDHMDB0001505
Secondary Accession Numbers
  • HMDB01505
Metabolite Identification
Common NameBenzene
DescriptionBenzene, 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.
Structure
Data?1582752206
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[6]AnnuleneChEBI
BenzenChEBI
BenzineChEBI
BenzolChEBI
BenzoleChEBI
Bicarburet OF hydrogenChEBI
Coal naphthaChEBI
CyclohexatrieneChEBI
Mineral naphthaChEBI
PheneChEBI
Phenyl hydrideChEBI
PyrobenzolChEBI
PyrobenzoleChEBI
(6)AnnuleneHMDB
AnnuleneHMDB
Aromatic alkaneHMDB
BenzeenHMDB
BenzinHMDB
BenzinumHMDB
Benzol 90HMDB
BenzoleneHMDB
BenzoloHMDB
BenzolumHMDB
BNZHMDB
Carbon oilHMDB
FenzenHMDB
Motor benzolHMDB
PolystreamHMDB
RNGHMDB
{[6]annulene}HMDB
Chemical FormulaC6H6
Average Molecular Weight78.1118
Monoisotopic Molecular Weight78.046950192
IUPAC Namebenzene
Traditional Namebenzene
CAS Registry Number71-43-2
SMILES
C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
InChI KeyUHOVQNZJYSORNB-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point5.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.79 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP2.03ALOGPS
logP1.97ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.06 m³·mol⁻¹ChemAxon
Polarizability8.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8bSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8bSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-c5901591488019f3ac5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004i-9000000000-70967112fec69784847cSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-004i-9000000000-92ccc664b07cb6c56de9Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0fb9-9000000000-2aae37aac9f2a02d5e8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positivesplash10-004i-9100000000-11f8463e7c6286637b1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-45ac36cbb443a00d6a17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-9cad19d98e6420c7b6a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-2dace4807cb04a7942deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b4ff542394722302be43Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-08f396d6cb4660e57caaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breath
  • Feces
  • Saliva
Tissue Locations
  • Bone Marrow
  • Liver
  • Lymphocyte
  • Skin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000384 (0.000320-0.000448) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
BloodDetected and Quantified0.000307 (0.000256-0.000384) uMChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
BreathDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Autism
  1. 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
  1. 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
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012843
KNApSAcK IDNot Available
Chemspider ID236
KEGG Compound IDC01407
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzene
METLIN ID6285
PubChem Compound241
PDB IDNot Available
ChEBI ID16716
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceCopisarow, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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. [PubMed:15920754 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Barbera N, Bulla G, Romano G: A fatal case of benzene poisoning. J Forensic Sci. 1998 Nov;43(6):1250-1. [PubMed:9846407 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]