Aroclor 1242 (CED0000019)

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:57 UTC

Update Date

2026-08-18 21:16:30 UTC

Accession Number

CHEM000026

Identification

Common Name

Aroclor 1242

Class

Small Molecule

Description

Aroclor 1242 belongs to the biphenyls and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous compound has a formula of C12H6Cl4 and an average molecular weight of 291.99 g/mol. At room temperature, it exists as a solid. It has been recorded as being found in or released from electrical and electronic equipment, specifically antennas, electric switches, fixed capacitors, and their manufacture. Aroclor 1242 interacts with several protein targets. It binds to the aryl hydrocarbon receptor (AHR), which disrupts cell function by altering gene transcription and inducing the expression of hepatic Phase I and Phase II enzymes, particularly the cytochrome P450 family. It causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor (ESR1 and ESR2). Additionally, binding to estrogen sulfotransferase (SULT1E1) can produce estrogenic effects, such as reproductive dysfunction, and stimulate the growth of certain cancer cells. The compound may bioaccumulate by binding to receptor proteins such as uteroglobin (SCGB1A1). Furthermore, inhibition of tyrosine 3-monooxygenase (TH) and aromatic-L-amino-acid decarboxylase (DDC) by PCBs is believed to cause decreased dopamine synthesis.

Contaminant Type

Aromatic Hydrocarbon
Coolant
Industrial/Workplace Toxin
Organic Compound
Organochloride
Plasticizer
Pollutant
Polychlorinated Biphenyl
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₂H₆Cl₄

Average Molecular Mass

291.988 g/mol

Monoisotopic Mass

289.922 g/mol

CAS Registry Number

53469-21-9

IUPAC Name

2,4-dichloro-1-(2,3-dichlorophenyl)benzene

Traditional Name

2,2',3,4'-tetrachlorobiphenyl

SMILES

ClC1=CC=C(C(Cl)=C1)C1=CC=CC(Cl)=C1Cl

InChI Identifier

InChI=1S/C12H6Cl4/c13-7-4-5-8(11(15)6-7)9-2-1-3-10(14)12(9)16/h1-6H

InChI Key

ALFHIHDQSYXSGP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Polychlorinated biphenyls

Alternative Parents

Substituents

Polychlorinated biphenyl
1,3-dichlorobenzene
1,2-dichlorobenzene
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane
Mitochondrion
Plasma Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

Oily liquids or solids that are colorless to light yellow.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	0.000277 mg/mL at 20 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Predicted Properties

Property	Value	Source
Water Solubility	3.3e-05 g/L	ALOGPS
logP	6.22	ALOGPS
logP	6.04	ChemAxon
logS	-7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.41 m³·mol⁻¹	ChemAxon
Polarizability	26.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-0190000000-9ed01fef291ce9306d25	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-77eb6950c0185c4cd686	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-16503659faa45922bc44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-a98add2243af52c2ec10	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-77eb6950c0185c4cd686	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-16503659faa45922bc44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-a98add2243af52c2ec10	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-323a066225501397657d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-323a066225501397657d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0290000000-7adbedd1e310eb2d529c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-ebc4bc6a9154ade1216d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0090000000-ebc4bc6a9154ade1216d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f6x-0290000000-f6a97f51078b8026b566	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-a0109030c31ebbacd6ce	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-d08422ec034d311ef02b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-8390000000-a4b513538b3606b02fb2	Not Available	View Spectrum
MS	MS Spectrum	splash10-0006-1290000000-a8da5a5a23af10768c15	Not Available	View Spectrum

Toxicity Profile

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. (1, 2, 5, 6)

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (9)

Minimum Risk Level

Intermediate Oral: 0.03 ug/kg/day (8)

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. (1)

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. (7)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
4250.0	mg/kg	Not Available	Rat	LD50	Oral	experimental	T14

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
506	Antennas	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

3 pathways

Cell cycle

Eicosanoids

Apoptosis

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	1458.82
Click to view 3D structure	Glycogen synthase kinase-3 alpha	P49840	Humans	Predicted (SEA)	1176.46
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q13627	Humans	Predicted (SEA)	1491.59
Click to view 3D structure	Tubulin alpha 4a	C5ISA2	Ovis aries	Predicted (SEA)	16.0369
Click to view 3D structure	Mitogen-activated protein kinase 9	P45984	Humans	Predicted (SEA)	1499.53
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	1482.87
Click to view 3D structure	Dual specificity protein kinase CLK4	Q9HAZ1	Humans	Predicted (SEA)	1635.38
Click to view 3D structure	Mitogen-activated protein kinase 8	P45983	Humans	Predicted (SEA)	1925.52
Click to view 3D structure	Cyclin-dependent kinase 5	Q00535	Humans	Predicted (SEA)	1824.47
Click to view 3D structure	Cyclin-dependent kinase 1	P06493	Humans	Predicted (SEA)	1733.16
Click to view 3D structure	Mitogen-activated protein kinase 14	Q16539	Humans	Predicted (SEA)	1804.23
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	2529.55
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	2221.82
Click to view 3D structure	BDNF/NT-3 growth factors receptor	Q16620	Humans	Predicted (SEA)	1991.31
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	2263.62
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	2086.59
Click to view 3D structure	Serine/threonine-protein kinase Chk1	O14757	Humans	Predicted (SEA)	2036.07
Click to view 3D structure	Serine/threonine-protein kinase N2	Q16513	Humans	Predicted (SEA)	1637.71
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	2410.99
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	2415.74
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	1942.96
Click to view 3D structure	Protein phosphatase 1 regulatory subunit 15A	O75807	Humans	Predicted (SEA)	4.35956
Click to view 3D structure	Protein phosphatase 1 regulatory subunit 15B	Q5SWA1	Humans	Predicted (SEA)	4.35956
Click to view 3D structure	Sigma intracellular receptor 2	Q8VD00	Mus musculus	Predicted (SEA)	7.00643
Click to view 3D structure	Serine/threonine-protein kinase TAO1	Q7L7X3	Humans	Predicted (SEA)	1973.32
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Sulfotransferase 1E1	P49888	Humans	Known	PCBs 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)
Click to view 3D structure	Aromatic-L-amino-acid decarboxylase	P20711	Humans	Known	PCB inhibition of aromatic-L-amino-acid decarboxylase is believed to cause decreased dopamine synthesis. (L4)
Click to view 3D structure	Aryl hydrocarbon receptor	P35869	Humans	Known	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. (A4)
Click to view 3D structure	Tyrosine 3-monooxygenase	P07101	Humans	Known	PCB inhibition of tyrosine 3-monooxygenase is believed to cause decreased dopamine synthesis. (L4)
Click to view 3D structure	Uteroglobin	P11684	Humans	Known	PCBs will bioaccumulate by binding to receptor proteins such as uteroglobin. (A30)