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Name Description
id 86
T3DB ID T3D0099
Name Ethylbenzene
Class SmallMolecule
Description Ethylbenzene 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.
Categories "Cigarette Toxin", "Household Toxin", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Industrial Precursor/Intermediate", "Aromatic Hydrocarbon", "Pollutant", "Food Toxin", "Metabolite", "Cigarette Toxin", "Household Toxin", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "Aethylbenzol", "alpha-methyltoluene", "Ethylbenzol", "Phenylethane"
CAS Number 100-41-4
Chemical Formula C8H10
Average Molecular Mass 106.17
Monoisotopic Mass 106.08
IUPAC Name ethylbenzene
Traditional Name ethylbenzene
SMILES CCC1=CC=CC=C1
InChI Identifier InChI=1S/C8H10/c1-2-8-6-4-3-5-7-8/h3-7H,2H2,1H3
InChI Key InChIKey=YNQLUTRBYVCPMQ-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class
Direct Parent Benzene and Substituted Derivatives
Alternate Parents "Hydrocarbons"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "Monocyclic Benzene Moiety", "Aromatic Homomonocyclic Compound", "Hydrocarbon"
Descriptors "an aromatic compound (MetaCyc)", "alkylbenzene (ChEBI)"
Status Detected and Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids "Blood"
Tissues
Pathways
State Liquid
Appearance
Melting Point -94.9°C
Boiling Point
Solubility 0.169 mg/mL at 25 °C [SANEMASA,I et al. (1982)]
LogP
Route of Exposure Oral (L311); inhalation (L311) ; dermal (L311).
Mechanism of Toxicity Changes 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. (L311, A186)
Metabolism Ethylbenzene 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. (L311)
Toxicity LD50: 3.5 g/kg (Oral, Rat) (L324) LD50: 77.4 g/kg (Dermal, Rabbit)(L324) LC50: 17.2 g/m3 (4000 ppm) (Inhalation, Rat) (L324)
Lethal Dose
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources Ethylbenzene 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. (L311)
Minimum Risk Level Acute Inhalation: 10 ppm (L134) Intermediate Inhalation: 0.7 ppm (L134) Chronic Inhalation: 0.3 ppm (L134) Intermediate Oral: 0.5 mg/kg/day (L134)
Health Effects Chronic 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. (L311, T52)
Symptoms Cough, 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. (L316)
Treatment Following 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. (T36)
DrugBank ID DB01722
HMDB ID HMDB59905
PubChem Compound ID 7500
ChEMBL ID CHEMBL371561
ChemSpider ID 7219
KEGG Compound ID C07111
UniProt ID 0
OMIM ID 0
ChEBI ID 16101
BioCyc ID CPD-9502
CTD ID C004912
Stitch ID Ethylbenzene
PDB ID
ACToR ID 606
Wikipedia Link http://en.wikipedia.org/wiki/Ethylbenzene
Creation Date 2009-03-06 18:58:04
Update Date 2014-12-24 20:21:06