Ethylbenzene (CHEM000090)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (17)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:04 UTC
Update Date2026-03-31 17:33:31 UTC
Accession NumberCHEM000090
Identification
Common NameEthylbenzene
ClassSmall Molecule
DescriptionEthylbenzene is an organic compound with the formula C6H5CH2CH3. 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. Although often present in small amounts in crude oil, ethylbenzene is produced in bulk quantities by combining benzene and ethylene in an acid-catalyzed chemical reaction. It is one ingredient of cigarette. The acute toxicity of ethylbenzene is low, with an LD50 of about 4 grams per kilogram of body weight. The longer term toxicity and carcinogenicity is ambiguous. Eye and throat sensitivity can occur when high level exposure to ethylbenzene in the air occurs. At higher level exposure, ethylbenzene can cause dizziness.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-MethyltolueneChEBI
AethylbenzolChEBI
EthylbenzolChEBI
EthylenzeneChEBI
PhenylethaneChEBI
a-MethyltolueneGenerator
Α-methyltolueneGenerator
1-EthylbenzeneHMDB
EBHMDB
EthylbenzeneHMDB
Chemical FormulaC8H10
Average Molecular Mass106.165 g/mol
Monoisotopic Mass106.078 g/mol
CAS Registry Number100-41-4
IUPAC Nameethylbenzene
Traditional Nameethylbenzene
SMILESCCC1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-94.9°C
Boiling PointNot Available
Solubility0.169 mg/mL at 25 °C [SANEMASA,I et al. (1982)]
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6bSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d72793Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6bSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d72793Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9300000000-c7e86064f086caf02674Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3d28e81794c61465b233Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ea2447a1e61e24730a44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-1824048a45b025a1f4aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8ca4acb96694435a7851Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-5b9ea9d3d5b6f3bbb587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-9600000000-dc68589987b1b4f1e625Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-f8066873e5f243968d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9300000000-2aecf2aac0a60843c353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9000000000-2708ae8f35c96209bba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-861947f0491f909a2588Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-1204b096ce8c38491d80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ffSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1cec483f116a110c0c16Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (5); inhalation (5) ; dermal (5).
Mechanism of ToxicityChanges in the integrity of the cell membrane after partitioning of ethylbenzene into the lipid bilayer may subsequently affect the function of membrane, particularly as a barrier and in energy transduction, and in the formation of a matrix for proteins and enzymes. Ethybenzene inhibits the activity of the astrocytic membrane ATPases, which helps regulate adequate intercellular levels of ions, nutrients, metabolic intermediates and precursors in the central nervous system. Thus, this may disturb the ability of the cells to maintain homeostasis. (5, 1)
MetabolismEthylbenzene is metabolized mainly through hydroxylation and then through conjugation reactions from which numerous metabolites have been isolated. Hydroxylation of ethylbenzene to 1-phenylethanol is catalyzed by cytochrome P-450 isoforms CYP2E1 and CYP2B6. 1-Phenylethanol is conjugated to glucuronide, which then is either excreted or converted to subsequent metabolites. Oxidation of 1-phenylethanol yields acetophenone, which is both excreted in the urine as a minor metabolite and further transformed. Continued oxidation of the side chain leads to the sequential formation of 2-hydroxyacetophenone, 1-phenyl-1,2-ethanediol, mandelic acid, and phenylglyoxylic acid. Minor pathways (e.g., ring hydroxylation) include glucuronide and sulfate conjugation with hydroxylated derivatives to form glucuronides and sulfates that are excreted in the urine. In humans exposed via inhalation, the major metabolites of ethylbenzene in the urine are mandelic acid (70%) and phenylglyoxylic acid (25%). Following dermal exposure of humans, however, excretion of mandelic acid was shown to be only 4.6% of the absorbed dose, which may indicate differences in the metabolic fate between inhalation and dermal exposure routes. (5)
Toxicity ValuesLD50: 3.5 g/kg (Oral, Rat) (7) LD50: 77.4 g/kg (Dermal, Rabbit)(7) LC50: 17.2 g/m3 (4000 ppm) (Inhalation, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesEthylbenzene is used 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. Exposure may occur from breathing contaminated air, drinking or eating food prepared with ethylbenzene-contaminated water, and through skin contact with products containing ethylbenzene, such as gasoline. (5)
Minimum Risk LevelAcute Inhalation: 10 ppm (3) Intermediate Inhalation: 0.7 ppm (3) Chronic Inhalation: 0.3 ppm (3) Intermediate Oral: 0.5 mg/kg/day (3)
Health EffectsChronic exposure to etylbenzene can lead to an increase in the mean number of lymphocytes and a decrease in hemoglobin levels. Acute duration and intermediate duration studies suggest that the auditory system is a sensitive target of ethylbenzene toxicity. Exposure ethylbenzene can lead to functional and organic disturbances (nervous system disturbances, toxic hepatitis and upper respiratory tract complaints). Metabolites of ethylbenzene have been shown to produce oxidative damage to DNA. (5, 9)
SymptomsCough, sore throat, dizziness, drowsiness, and headache follow inhalation or ingestion exposure to ethylbenzene. Ingestion exposure can also lead to burning sensation in the throat and chest. Skin or eyes contact to ethylbenzene can lead to redness and pain of the exposed surface. (6)
TreatmentFollowing oral exposure, a gastric lavage is recommended. Protect airway by placement in Trendelenburg and left lateral decubitus position or by endotracheal intubation. Control any seizures first. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. Some chemicals can produce systemic poisoning by absorption through intact skin. Carefully observe patients with dermal exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary. (8)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0059905
FooDB IDFDB004763
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDETHYLBENZENE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthylbenzene
Chemspider ID7219
ChEBI ID16101
PubChem Compound ID7500
Kegg Compound IDC07111
YMDB IDYMDB16013
ECMDB IDM2MDB004638
References
Synthesis Reference

Guenther Heimlich, Gregor Tremmel, Manfred Lieb, “Continuous preparation of ethylbenzene in a heterogeneous-phase reaction.” U.S. Patent US4431854, issued July, 1950.

MSDSNot Available
General ReferencesNot Available