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Name Description
id 12
T3DB ID T3D0013
Name Aroclor 1254
Class SmallMolecule
Description Aroclor 1254 is a commercial mixture of PCBs with an average chlorine content of 54%. It is composed of mainly pentachlorobiphenyls (71.44%) and hexachlorobuphenyls (21.97%) and also includes mono-, bi-, tri, tetra-, hexa, and nonachlorinated homologs. Polychlorinated biphenyls (PCBs) are a group of 209 synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. PCBs were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate in the environment and cause harmful health effects. However, PCBs do not break down readily and are still found in the environment. (L4)
Categories "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Polychlorinated Biphenyl", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Coolant", "Plasticizer", "Polychlorinated Biphenyl", "Aromatic Hydrocarbon", "Pollutant", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "2,2',3,3',4'-Pentachlorobiphenyl", "2,2',3,3',4-pentachloro-1,1'-Biphenyl", "2,3,4,2',3'-Pentachlorobiphenyl", "Arochlor 1254", "Polychlorinated biphenyl (aroclor 1254)", "polychlorinated biphenyl 1254"
CAS Number 11097-69-1
Chemical Formula C12H5Cl5
Average Molecular Mass 326.43
Monoisotopic Mass 323.88
IUPAC Name 1,2,3-trichloro-4-(2,3-dichlorophenyl)benzene
Traditional Name 1,2,3-trichloro-4-(2,3-dichlorophenyl)benzene
SMILES ClC1=CC=CC(=C1Cl)C1=C(Cl)C(Cl)=C(Cl)C=C1
InChI Identifier InChI=1S/C12H5Cl5/c13-8-3-1-2-6(10(8)15)7-4-5-9(14)12(17)11(7)16/h1-5H
InChI Key InChIKey=AUGNBQPSMWGAJE-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Biphenyls and Derivatives
Direct Parent Chlorinated Biphenyls
Alternate Parents "Dichlorobenzenes", "Aryl Chlorides", "Organochlorides"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "chlorobenzene", "aryl chloride", "organochloride", "1,2-dichlorobenzene", "Aromatic Homomonocyclic Compound", "Halobenzene", "Aryl Halide", "Organohalogen Compound", "Polychlorinated biphenyl"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Actin Cytoskeleton", "Cell junction", "Cell surface", "Cytoskeleton", "Cytosol", "Endoplasmic reticulum", "Extracellular", "Golgi apparatus", "Lysosome", "Membrane", "Membrane Fraction", "Microsome", "Mitochondrial Matrix", "Mitochondrion", "Nuclear Membrane", "Peroxisome", "Plasma Membrane", "Ribosome", "Secretory vesicle"
Biofluids
Tissues
Pathways "Apoptosis", "Ovarian Steroidogenesis", "Cell cycle", "Long-term potentiation", "Glutathione Metabolism", "Tryptophan Metabolism", "Phenylalanine metabolism", "Fatty acid Metabolism", "Fatty Acid Biosynthesis", "Anticonvulsants", "Abc transporters"
State Solid
Appearance Oily liquids or solids that are colorless to light yellow.
Melting Point
Boiling Point 365-390 °C
Solubility 4.3e-05 mg/mL at 20 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogP
Route of Exposure Oral (L4) ; inhalation (L4) ; dermal (L4)
Mechanism of Toxicity The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)
Metabolism PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are transported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose tissue, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)
Toxicity LD50: 1010 mg/kg (Oral, Rat) (L135) LD50: 358 mg/kg (Intravenous, Rat) (L135) LD50: 880 mg/kg (Intraperitoneal, Rat) (L135)
Lethal Dose
Carcinogenicity 1, carcinogenic to humans. (L135)
Uses/Sources PCBs were used as coolants and lubricants in transformers, capacitors, and other electrical devices (such as fluorescent lights and refridgerators) produced before 1977. PCBs may contaminate the air and water near hazardous waste sites. In addition, PCBs bioaccumulate in the environment and may be found in fish, meat, and dairy products. (L4)
Minimum Risk Level Intermediate Oral: 0.03 ug/kg/day (L134)
Health Effects The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)
Symptoms Chronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)
Treatment There are no specific treatments for PCB poisoning, since it is not usually recognized until after substantial chronic exposure. Only preventing further exposure and treating the observed symptoms can be done. Acute inhalation can be treated by administering oxygen. (L4)
DrugBank ID
HMDB ID
PubChem Compound ID 40470
ChEMBL ID
ChemSpider ID 36975
KEGG Compound ID
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID
CTD ID D020111
Stitch ID Aroclor 1254
PDB ID
ACToR ID 101
Wikipedia Link http://en.wikipedia.org/wiki/Polychlorinated_biphenyl
Creation Date 2009-03-06 18:57:55
Update Date 2014-12-24 20:20:52