Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:04 UTC
Update Date2014-12-24 20:21:06 UTC
Accession NumberT3D0099
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.
Compound Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Aethylbenzol
alpha-methyltoluene
Ethylbenzol
Phenylethane
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 KeyInChIKey=YNQLUTRBYVCPMQ-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)]
LogPNot Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6bView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d72793View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e311097b1353d1f46e6eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-c2b5306fbaeb48134d6bView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0a4i-1900000000-ff5c54f00a3ae0d72793View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9300000000-c7e86064f086caf02674View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3d28e81794c61465b233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ea2447a1e61e24730a44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-1824048a45b025a1f4aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8ca4acb96694435a7851View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-5b9ea9d3d5b6f3bbb587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-9600000000-dc68589987b1b4f1e625View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1cec483f116a110c0c16View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (7); inhalation (7) ; dermal (7).
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. (7, 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. (7)
Toxicity ValuesLD50: 3.5 g/kg (Oral, Rat) (9) LD50: 77.4 g/kg (Dermal, Rabbit)(9) LC50: 17.2 g/m3 (4000 ppm) (Inhalation, Rat) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (6)
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. (7)
Minimum Risk LevelAcute Inhalation: 10 ppm (5) Intermediate Inhalation: 0.7 ppm (5) Chronic Inhalation: 0.3 ppm (5) Intermediate Oral: 0.5 mg/kg/day (5)
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. (7, 4)
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. (8)
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. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01722
HMDB IDHMDB59905
PubChem Compound ID7500
ChEMBL IDCHEMBL371561
ChemSpider ID7219
KEGG IDC07111
UniProt IDNot Available
OMIM ID
ChEBI ID16101
BioCyc IDCPD-9502
CTD IDC004912
Stitch IDEthylbenzene
PDB IDNot Available
ACToR ID606
Wikipedia LinkEthylbenzene
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.

MSDST3D0099.pdf
General References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
  2. Sams C, Loizou GD, Cocker J, Lennard MS: Metabolism of ethylbenzene by human liver microsomes and recombinant human cytochrome P450s (CYP). Toxicol Lett. 2004 Mar 7;147(3):253-60. [15104117 ]
  3. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  4. International Labour Office (1983). Encyclopedia of Occupational Health and Safety. Volumes. I and II. Geneva, Switzerland: International Labour Office.
  5. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  7. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Toxicological profile for ethylbenzene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  8. International Programme on Chemical Safety (IPCS) INCHEM (2007). Poison Information Monograph for Ethylbenzne. [Link]
  9. International Programme on Chemical Safety (IPCS) INCHEM (1996). Environmental Health Criteria for Ethylbenzene. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Signal transducer activity
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of the calcium.
Gene Name:
ATP2C1
Uniprot ID:
P98194
Molecular Weight:
100576.42 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Metal ion binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium.
Gene Name:
ATP2C2
Uniprot ID:
O75185
Molecular Weight:
103186.475 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Pdz domain binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
Gene Name:
ATP2B1
Uniprot ID:
P20020
Molecular Weight:
138754.045 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Protein c-terminus binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
Gene Name:
ATP2B2
Uniprot ID:
Q01814
Molecular Weight:
136875.18 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Pdz domain binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell.
Gene Name:
ATP2B3
Uniprot ID:
Q16720
Molecular Weight:
134196.025 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Scaffold protein binding
Specific Function:
Calcium/calmodulin-regulated and magnesium-dependent enzyme that catalyzes the hydrolysis of ATP coupled with the transport of calcium out of the cell (PubMed:8530416). By regulating sperm cell calcium homeostasis, may play a role in sperm motility (By similarity).
Gene Name:
ATP2B4
Uniprot ID:
P23634
Molecular Weight:
137919.03 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Protein homodimerization activity
Specific Function:
Key regulator of striated muscle performance by acting as the major Ca(2+) ATPase responsible for the reuptake of cytosolic Ca(2+) into the sarcoplasmic reticulum. Catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
Gene Name:
ATP2A1
Uniprot ID:
O14983
Molecular Weight:
110251.36 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
S100 protein binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the translocation of calcium from the cytosol to the sarcoplasmic reticulum lumen. Isoform 2 is involved in the regulation of the contraction/relaxation cycle.
Gene Name:
ATP2A2
Uniprot ID:
P16615
Molecular Weight:
114755.765 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Metal ion binding
Specific Function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of calcium. Transports calcium ions from the cytosol into the sarcoplasmic/endoplasmic reticulum lumen. Contributes to calcium sequestration involved in muscular excitation/contraction.
Gene Name:
ATP2A3
Uniprot ID:
Q93084
Molecular Weight:
113976.23 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A2
Uniprot ID:
P50993
Molecular Weight:
112264.385 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A3
Uniprot ID:
P13637
Molecular Weight:
111747.51 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
Gene Name:
ATP1A4
Uniprot ID:
Q13733
Molecular Weight:
114165.44 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
Gene Name:
ATP1B1
Uniprot ID:
P05026
Molecular Weight:
35061.07 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
Gene Name:
ATP1B2
Uniprot ID:
P14415
Molecular Weight:
33366.925 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
Gene Name:
ATP1B3
Uniprot ID:
P54709
Molecular Weight:
31512.34 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]
General Function:
Transporter activity
Specific Function:
May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
Gene Name:
FXYD2
Uniprot ID:
P54710
Molecular Weight:
7283.265 Da
References
  1. Vaalavirta L, Tahti H: Astrocyte membrane Na+, K(+)-ATPase and Mg(2+)-ATPase as targets of organic solvent impact. Life Sci. 1995;57(24):2223-30. [7475975 ]