Record Information
Version1.0
Creation Date2009-03-06 18:57:55 UTC
Update Date2026-04-05 15:23:50 UTC
Accession NumberCHEM000011
Identification
Common NameAroclor 1254
ClassSmall Molecule
DescriptionAroclor 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. (7)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Coolant
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Plasticizer
  • Pollutant
  • Polychlorinated Biphenyl
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Aroclor-1254MeSH
Chlorodiphenyl (54% chlorine)MeSH
Chemical FormulaC12H5Cl5
Average Molecular Mass326.433 g/mol
Monoisotopic Mass323.883 g/mol
CAS Registry Number11097-69-1
IUPAC Name1,2,3-trichloro-4-(2,3-dichlorophenyl)benzene
Traditional Name1,2,3-trichloro-4-(2,3-dichlorophenyl)benzene
SMILESClC1=CC=C(C(Cl)=C1Cl)C1=C(Cl)C(Cl)=CC=C1
InChI IdentifierInChI=1S/C12H5Cl5/c13-8-3-1-2-6(10(8)15)7-4-5-9(14)12(17)11(7)16/h1-5H
InChI KeyAUGNBQPSMWGAJE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentPolychlorinated biphenyls
Alternative Parents
Substituents
  • Polychlorinated biphenyl
  • 1,2-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
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
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Ovarian SteroidogenesisNot AvailableNot Available
Cell cycleNot Availablemap04110
Long-term potentiationNot Availablemap04720
Glutathione MetabolismSMP00015 map00480
Tryptophan MetabolismSMP00063 map00380
Phenylalanine metabolismNot Availablemap00360
Fatty acid MetabolismSMP00051 map00071
Fatty Acid BiosynthesisSMP00456 map00061
AnticonvulsantsNot AvailableNot Available
Abc transportersNot Availablemap02010
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceOily liquids or solids that are colorless to light yellow.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point365-390 °C
Solubility4.3e-05 mg/mL at 20 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility6.6e-06 g/LALOGPS
logP6.77ALOGPS
logP6.64ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.22 m³·mol⁻¹ChemAxon
Polarizability28.61 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1049000000-68987fd0c86e93508aa7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1bb2418ddea54dfa96a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-5a271c8002a095463aa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0019000000-43c82488b71d37ac0a50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-61e888c218b06cb3b74fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-61e888c218b06cb3b74fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0029000000-4349b6d9aedfc23a9e4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-47057e0cfa248ce6ed12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-47057e0cfa248ce6ed12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0159000000-66b1ee279c60bf46667fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-3882219cf7a9a544b0b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-3882219cf7a9a544b0b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0009000000-7d66a3a0a88bf94f9eb9Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-3879000000-81e339b03ec3db709addSpectrum
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityThe 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. (1, 2, 5, 6)
MetabolismPCBs 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. (7, 10)
Toxicity ValuesLD50: 1010 mg/kg (Oral, Rat) (9) LD50: 358 mg/kg (Intravenous, Rat) (9) LD50: 880 mg/kg (Intraperitoneal, Rat) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (9)
Uses/SourcesPCBs 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. (7)
Minimum Risk LevelIntermediate Oral: 0.03 ug/kg/day (8)
Health EffectsThe 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. (7)
SymptomsChronic 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. (1)
TreatmentThere 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. (7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID40470
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available