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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-03-07 21:35:59 UTC
Update Date2022-03-07 03:17:38 UTC
HMDB IDHMDB0059905
Secondary Accession Numbers
  • HMDB59905
Metabolite Identification
Common NameEthylbenzene
DescriptionEthylbenzene, also known as ethylbenzol or phenylethane, 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. Chronic exposure to etylbenzene can lead to an increase in the mean number of lymphocytes and a decrease in hemoglobin levels. Ethylbenzene is possibly neutral. Outside of the human body, Ethylbenzene is found, on average, in the highest concentration within black walnuts and safflowers. Ethylbenzene has also been detected, but not quantified in, several different foods, such as garden tomato (var.), cauliflowers, cucumbers, cherry tomato, and garden tomato. This could make ethylbenzene a potential biomarker for the consumption of these foods. This aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a commonly used plastic material. Ethylbenzene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Treat dermal irritation or burns with standard topical therapy.
Structure
Data?1601264182
Synonyms
ValueSource
alpha-MethyltolueneChEBI
AethylbenzolChEBI
EthylbenzolChEBI
EthylenzeneChEBI
PhenylethaneChEBI
a-MethyltolueneGenerator
Α-methyltolueneGenerator
1-EthylbenzeneHMDB
EBHMDB
EthylbenzeneHMDB
Chemical FormulaC8H10
Average Molecular Weight106.165
Monoisotopic Molecular Weight106.07825032
IUPAC Nameethylbenzene
Traditional Nameethylbenzene
CAS Registry Number100-41-4
SMILES
CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3
InChI KeyYNQLUTRBYVCPMQ-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

Adverse health effect

Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.27ALOGPS
logP2.93ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.7 m³·mol⁻¹ChemAxon
Polarizability12.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.6731661259
DarkChem[M-H]-118.95331661259
DeepCCS[M+H]+123.22830932474
DeepCCS[M-H]-120.48430932474
DeepCCS[M-2H]-156.96730932474
DeepCCS[M+Na]+131.67230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthylbenzeneCCC1=CC=CC=C11135.3Standard polar33892256
EthylbenzeneCCC1=CC=CC=C1865.8Standard non polar33892256
EthylbenzeneCCC1=CC=CC=C1863.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethylbenzene EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylbenzene EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylbenzene CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d727932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylbenzene EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylbenzene EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethylbenzene CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d727932018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylbenzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9300000000-c7e86064f086caf026742016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylbenzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1cec483f116a110c0c162014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 10V, Positive-QTOFsplash10-0a4i-0900000000-3d28e81794c61465b2332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 20V, Positive-QTOFsplash10-0a4i-1900000000-ea2447a1e61e24730a442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 40V, Positive-QTOFsplash10-052f-9100000000-1824048a45b025a1f4aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 10V, Negative-QTOFsplash10-0a4i-0900000000-8ca4acb96694435a78512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 20V, Negative-QTOFsplash10-0a4i-0900000000-5b9ea9d3d5b6f3bbb5872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 40V, Negative-QTOFsplash10-0a70-9600000000-dc68589987b1b4f1e6252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 10V, Positive-QTOFsplash10-0a4i-0900000000-f8066873e5f243968d612021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 20V, Positive-QTOFsplash10-056r-9300000000-2aecf2aac0a60843c3532021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 40V, Positive-QTOFsplash10-00ou-9000000000-2708ae8f35c96209bba02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 10V, Negative-QTOFsplash10-0a4i-0900000000-861947f0491f909a25882021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 20V, Negative-QTOFsplash10-0a4i-2900000000-1204b096ce8c38491d802021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylbenzene 40V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Breath
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000377 (0.000349-0.000405) uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
BloodDetected and Quantified0.000301 (0.000283-0.000320) uMChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Asthma
  1. Gahleitner F, Guallar-Hoyas C, Beardsmore CS, Pandya HC, Thomas CP: Metabolomics pilot study to identify volatile organic compound markers of childhood asthma in exhaled breath. Bioanalysis. 2013 Sep;5(18):2239-47. doi: 10.4155/bio.13.184. [PubMed:24053239 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004763
KNApSAcK IDNot Available
Chemspider ID7219
KEGG Compound IDC07111
BioCyc IDETHYLBENZENE
BiGG IDNot Available
Wikipedia LinkEthylbenzene
METLIN IDNot Available
PubChem Compound7500
PDB IDNot Available
ChEBI ID16101
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029806
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available