Aroclor 1254 (CED0000009)

Record Information
Version1.0
Creation Date2009-03-06 18:57:55 UTC
Update Date2026-08-18 21:13:49 UTC
Accession NumberCHEM000011
Identification
Common NameAroclor 1254
ClassSmall Molecule
Description
Aroclor 1254 belongs to the biphenyls and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous compound has a formula of C12H5Cl5 and an average molecular weight of 326.43 g/mol. It exists as a solid at room temperature. Recorded sources of the compound include household cleaning and consumer products such as pipe accessories, as well as electrical and electronic equipment including magnets and electrically stimulated smoking devices. Exposure can occur via inhalation (PMC10757425). Biologically, Aroclor 1254 acts as a neurotoxin and a carcinogenic agent. The compound interacts with several protein targets to produce various effects. It inhibits ATP-citrate synthase, which leads to a decrease in fatty acid synthesis. Inhibition of tyrosine 3-monooxygenase and aromatic-L-amino-acid decarboxylase is believed to cause decreased dopamine synthesis. Aroclor 1254 causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor beta (ESR2) and estrogen receptor (ESR1). Additionally, binding to estrogen sulfotransferase (SULT1E1) can produce other estrogenic effects, such as reproductive dysfunction, and may stimulate the growth of certain cancer cells. Dioxin-like PCBs bind to the aryl hydrocarbon receptor (AHR), disrupting cell function by altering gene transcription, specifically inducing the expression of hepatic Phase I and Phase II enzymes such as the cytochrome P450 family. Finally, the compound can bioaccumulate by binding to receptor proteins such as uteroglobin (SCGB1A1).
Contaminant Type
  • Aromatic Hydrocarbon
  • Coolant
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Plasticizer
  • Pollutant
  • Polychlorinated Biphenyl
  • Synthetic Compound
Chemical Structure
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-1049000000-68987fd0c86e93508aa7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-1bb2418ddea54dfa96a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-5a271c8002a095463aa5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0019000000-43c82488b71d37ac0a50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-61e888c218b06cb3b74fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-61e888c218b06cb3b74fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0029000000-4349b6d9aedfc23a9e4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-47057e0cfa248ce6ed12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-47057e0cfa248ce6ed12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0159000000-66b1ee279c60bf46667fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-3882219cf7a9a544b0b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-3882219cf7a9a544b0b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-7d66a3a0a88bf94f9eb9Not AvailableView Spectrum
MSMS Spectrumsplash10-004i-3879000000-81e339b03ec3db709addNot AvailableView Spectrum
Toxicity Profile
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)
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (9)
Minimum Risk LevelIntermediate Oral: 0.03 ug/kg/day (8)
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)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1010.0mg/kgNot AvailableRatLD50OralexperimentalL135
358.0mg/kgNot AvailableRatLD50IntravenousexperimentalL135
880.0mg/kgNot AvailableRatLD50IntraperitonealexperimentalL135
Health Effects
Health EffectRelationshipDirectionReference
glucose intoleranceassociated_withNot AvailablePMC10073482
Exposure Sources
Source IDSourceSectorReference
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
Pathways
11 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Protein phosphatase 1 regulatory subunit 15A structureClick to view 3D structureProtein phosphatase 1 regulatory subunit 15AO75807HumansPredicted (SEA)2.33548
Protein phosphatase 1 regulatory subunit 15B structureClick to view 3D structureProtein phosphatase 1 regulatory subunit 15BQ5SWA1HumansPredicted (SEA)2.33548
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)2165.92
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)2537.26
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)1575.05
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)1349.59
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)1366.72
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)3433.15
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)2322.79
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)3386.13
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)416.96
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)3531.79
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)2086.67
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)1461.15
Threonine aspartase 1 structureClick to view 3D structureThreonine aspartase 1Q9H6P5HumansPredicted (SEA)69.5194
Click to view 3D structureNAD-dependent histone deacetylase SIR2P06700Saccharomyces cerevisiae S288cPredicted (SEA)7.08428
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)4768.81
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)3175.94
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)4025.35
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)1588.59
Click to view 3D structureSigma non-opioid intracellular receptor 1Q9R0C9Rattus norvegicusPredicted (SEA)1374.9
Sodium channel protein type 2 subunit alpha structureClick to view 3D structureSodium channel protein type 2 subunit alphaQ99250HumansPredicted (SEA)598.661
Click to view 3D structureTyrosine-protein phosphatase non-receptor type 11P35235Mus musculusPredicted (SEA)20.8636
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)5385.76
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)2902.69
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Sulfotransferase 1E1 structureClick to view 3D structureSulfotransferase 1E1P49888HumansKnownPCBs can cause endocrine disurption by binding to estrogen sulfotransferase, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. (A3, A66)
Aromatic-L-amino-acid decarboxylase structureClick to view 3D structureAromatic-L-amino-acid decarboxylaseP20711HumansKnownPCB inhibition of aromatic-L-amino-acid decarboxylase is believed to cause decreased dopamine synthesis. (L4)
Aryl hydrocarbon receptor structureClick to view 3D structureAryl hydrocarbon receptorP35869HumansKnownDioxin-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. (A4)
Tyrosine 3-monooxygenase structureClick to view 3D structureTyrosine 3-monooxygenaseP07101HumansKnownPCB inhibition of tyrosine 3-monooxygenase is believed to cause decreased dopamine synthesis. (L4)
Uteroglobin structureClick to view 3D structureUteroglobinP11684HumansKnownPCBs will bioaccumulate by binding to receptor proteins such as uteroglobin. (A30)
Concentrations
Not Available
External Links
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 References