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Name Description
id 6
T3DB ID T3D0006
Name Benzene
Class SmallMolecule
Description Benzene is a toxic, volatile, flammable liquid hydrocarbon biproduct of coal distillation. Chronic benzene exposure produces hematotoxicity, bone marrow dysplasia (Displasia is a pre-neoplastic or pre-cancerous change). (A7669). It is used as an industrial solvent in paints, varnishes, lacquer thinners, gasoline, etc. Benzene causes central nervous system damage acutely and is carcinogenic. It was formerly used as parasiticide.
Categories "Cigarette Toxin", "Pesticide", "Household Toxin", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Food Toxin", "Natural Toxin"
Types "Organic Compound", "Industrial Precursor/Intermediate", "Aromatic Hydrocarbon", "Solvent", "Gasoline Additive/Component", "Pesticide", "Pollutant", "Food Toxin", "Metabolite", "Cigarette Toxin", "Household Toxin", "Industrial/Workplace Toxin", "Natural Compound"
Synonyms "Annulene", "Aromatic alkane", "Benzeen", "Benzen", "Benzin", "Benzine", "Benzinum", "Benzol", "Benzol 90", "Benzole", "Benzolene", "Benzolo", "Benzolum", "Bicarburet of hydrogen", "BNZ", "Carbon oil", "Coal naphtha", "Cyclohexatriene", "Fenzen", "Mineral naphtha", "Motor benzol", "Phene", "Phenyl hydride", "Polystream", "Pyrobenzol", "Pyrobenzole", "RNG"
CAS Number 71-43-2
Chemical Formula C6H6
Average Molecular Mass 78.11
Monoisotopic Mass 78.05
IUPAC Name benzene
Traditional Name benzene
SMILES C1=CC=CC=C1
InChI Identifier InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
InChI Key InChIKey=UHOVQNZJYSORNB-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 "benzenes (ChEBI)", "aromatic annulene (ChEBI)", "an aromatic compound (MetaCyc)"
Status Detected and Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids "Blood"
Tissues "Bone Marrow", "Liver", "Lymphocyte", "Skin"
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point 5.5°C
Boiling Point 80.1 °C
Solubility 1.79 mg/mL at 25°C [MAY,WE et al. (1983)]
LogP 2.13
Route of Exposure Inhalation (L5)
Mechanism of Toxicity The toxic agents of benzene are its metabolites. Benzene is able increase its toxicity by inducing cytochrome P450 2E1, its main metabolic enzyme. Benzene's primary toxic effects are decreases in haematological cell counts and bone marrow cellularity. The decrease in blood cell count may be due to the binding of metabolites such as benzene oxide to the blood proteins albumin and haemoglobin. In the bone marrow, phenolic metabolites can be metabolized by bone marrow peroxidases to highly reactive semiquinone radicals and quinones that stimulate the production of reactive oxygen species. This and direct metabolite binding leads to damage to tubulin, histone proteins, and topoisomerase II. Some metabolites also exert mutagenic effects by inhibiting other DNA associated proteins, such as mitochondrial DNA polymerase and ribonucleotide reductase, as well as covalently binding to DNA itself, causing effects such as strand breakage, mitotic recombination, chromosome translocations, and aneuploidy. (L5)
Metabolism Benzene is absorbed readily following inhalation or oral exposure. It enters the bloodstream and is rapidly distributed throughout the body, tending to accumulate in fatty tissues. Benzene is exhaled unchanged by the lungs, as well as metabolized in the liver to benzene oxide by cytochrome P450 enzymes. Benzene oxide is further converted into phenol, catechol, and hydroquinone, which are excreted in the urine as glucuronide or sulfate conjugates. (T7)
Toxicity LD50: 3306 mg/kg (Oral, Rat) (T14) LD50 340 mg/kg (Intraperitoneal, Mouse) (T14) LC50: 9980 ppm (Inhalation, Mouse) (T14)
Lethal Dose 50-500 mg/kg (oral) or 20 000 ppm (inhaled) for an adult human. (L138)
Carcinogenicity 1, carcinogenic to humans. (L135)
Uses/Sources Benzene is often used as an intermediate to make chemicals needed for the production of plastics, resins, and nylon and other synthetic fibers. It is also used to make some types of rubbers, lubricants, dyes, detergents, drugs, and pesticides. Natural sources of benzene include emissions from volcanoes, forest fires, crude oil, gasoline, and cigarette smoke. (L5)
Minimum Risk Level Acute Inhalation: 0.009 ppm (L134) Intermediate Inhalation: 0.006 ppm (L134) Chronic Inhalation: 0.003 ppm (L134) Chronic Oral: 0.0005 mg/kg/day (L134)
Health Effects Benzene causes harmful effects on the bone marrow and also decreases blood cell counts, leading to blood disorders such as anemia. It can also cause excessive bleeding and affect the immune system, increasing the chance for infection. Benzene is also a known carcinogen, as chronic exposure to high levels has been shown to cause leukemia, particularly acute myelogenous leukemia. (L5)
Symptoms Breathing benzene can cause drowsiness, dizziness, rapid heart rate, headaches, tremors, confusion, and unconsciousness. Ingestion can result in vomiting, irritation of the stomach, dizziness, sleepiness, convulsions, and rapid heart rate. (L5)
Treatment There is no known antidote for benzene and poisoning is first treated by preventing further exposure. If inhaled, respiratory assist may be necessary. If ingested, gastric lavage may be performed, or activated charcoal can be administered. (T8)
DrugBank ID
HMDB ID HMDB01505
PubChem Compound ID 241
ChEMBL ID CHEMBL277500
ChemSpider ID 236
KEGG Compound ID C01407
UniProt ID 0
OMIM ID 111300
ChEBI ID 16716
BioCyc ID BENZENE
CTD ID D001554
Stitch ID Benzene
PDB ID BNZ
ACToR ID 136
Wikipedia Link http://en.wikipedia.org/wiki/benzene
Creation Date 2009-03-06 18:57:54
Update Date 2014-12-24 20:20:50