2,2',5,5'-TETRACHLOROBIPHENYL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H6Cl4
Molecular Weight	291.988
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2,2',5,5'-TETRACHLOROBIPHENYL

Structure Search

SMILES

ClC1=CC=C(Cl)C(=C1)C2=CC(Cl)=CC=C2Cl

InChI

InChIKey=HCWZEPKLWVAEOV-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H6Cl4
Molecular Weight	291.988
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Detection and measurement of the agonistic activities of PCBs and mono-hydroxylated PCBs to the constitutive androstane receptor using a recombinant yeast assay.	2015-10	26231822
Inhibitory effects on osteoblast differentiation in vitro by the polychlorinated biphenyl mixture Aroclor 1254 are mainly associated with the dioxin-like constituents.	2015-08	25795401
Lactational exposure to low levels of the six indicator non-dioxin-like polychlorinated biphenyls induces DNA damage and repression of neuronal activity, in juvenile male mice.	2015-02-03	25510870
Dopamine-dependent behavior in adult rats after perinatal exposure to purity-controlled polychlorinated biphenyl congeners (PCB52 and PCB180).	2014-01-03	24459701
Role of the nuclear xenobiotic receptors CAR and PXR in induction of cytochromes P450 by non-dioxinlike polychlorinated biphenyls in cultured rat hepatocytes.	2013-10-01	23770461
Perinatal exposure to purity-controlled polychlorinated biphenyl 52, 138, or 180 alters toxicogenomic profiles in peripheral blood of rats after 4 months.	2013-08-19	23829299
Neurodevelopmental and behavioral toxicity via lactational exposure to the sum of six indicator non-dioxin-like-polychlorinated biphenyls (∑6 NDL-PCBs) in mice.	2012-09-04	22595366
Some OH-PCBs are more potent inhibitors of aromatase activity and (anti-) glucocorticoids than non-dioxin like (NDL)-PCBs and MeSO₂-PCBs.	2011-10-10	21782008
Transcriptomics identifies differences between ultrapure non-dioxin-like polychlorinated biphenyls (PCBs) and dioxin-like PCB126 in cultured peripheral blood mononuclear cells.	2011-09-05	21703328
Auditory effects of developmental exposure to purity-controlled polychlorinated biphenyls (PCB52 and PCB180) in rats.	2011-07	21464466
In vitro toxicity profiling of ultrapure non-dioxin-like polychlorinated biphenyl congeners and their relative toxic contribution to PCB mixtures in humans.	2011-05	21357386
Investigation on the inclusions of PCB52 with cyclodextrins by performing DFT calculations and molecular dynamics simulations.	2010-12-23	21087060
Activation and potentiation of human GABAA receptors by non-dioxin-like PCBs depends on chlorination pattern.	2010-11	20819908
Polychlorinated biphenyls (PCB-153) and (PCB-77) absorption in human liver (HepG2) and kidney (HK2) cells in vitro: PCB levels and cell death.	2010-11	20723988
The effect of olestra on the absorption, excretion and storage of 2,2',5,5' tetrachlorobiphenyl; 3,3',4,4' tetrachlorobiphenyl; and perfluorooctanoic acid.	2010-11	19616301
Developmental exposure to polychlorinated biphenyls 52, 138 or 180 affects differentially learning or motor coordination in adult rats. Mechanisms involved.	2010-06-02	20223283
Polychlorinated biphenyls PCB 52, PCB 180, and PCB 138 impair the glutamate-nitric oxide-cGMP pathway in cerebellar neurons in culture by different mechanisms.	2010-04-19	20297801
Determination of organochlorine pesticide and polychlorinated biphenyl levels in adipose tissue of infertile men.	2010-03	19252989
Non-dioxin-like-PCBs phosphorylate Mdm2 at Ser166 and attenuate the p53 response in HepG2 cells.	2009-12-10	19751709
In vivo biotransformation of 3,3',4,4'-tetrachlorobiphenyl by whole plants-poplars and switchgrass.	2009-10-01	19848168
Cytochrome P450-dependent metabolism of PCB52 in the nematode Caenorhabditis elegans.	2009-08-01	19563772
Protective role of estrogen receptor-alpha on lower chlorinated PCB congener-induced DNA damage and repair in human tumoral breast cells.	2009-07-10	19433264
[Metabolism of 2,2',5,5'-tetrachlorobiphenyl (CB52) by rabbit liver microsomes].	2009-05	19588850
Isolation and characterisation of polychlorinated biphenyl (PCB) degrading fungi from a historically contaminated soil.	2009-01-12	19138404
Immune cell counts and risks of respiratory infections among infants exposed pre- and postnatally to organochlorine compounds: a prospective study.	2008-12-04	19055819
Experimental verification of a model describing solid phase microextraction (SPME) of freely dissolved organic pollutants in sediment porewater.	2008-08	18597813
Serum concentrations of indicator PCB congeners in the Czech adult population.	2008-07	18547604
Pesticide contamination profiles of water, sediment and aquatic organisms in the effluent of Gaobeidian wastewater treatment plant.	2008-07	18472141
Genotoxic effects of PCB 52 and PCB 77 on cultured human peripheral lymphocytes.	2008-06-30	18573685
Differential inhibition of hepatic microsomal alkoxyresorufin O-dealkylation activities by tetrachlorobiphenyls.	2007-08-15	17586480
Cytochrome P450s and short-chain dehydrogenases mediate the toxicogenomic response of PCB52 in the nematode Caenorhabditis elegans.	2007-06-29	17499272
Pathways and products of the degradation of PCBs by the sodium dispersion method.	2007-06	17368509
Ontogenetic alterations in molecular and structural correlates of dendritic growth after developmental exposure to polychlorinated biphenyls.	2007-04	17450224
Polyethylene devices: passive samplers for measuring dissolved hydrophobic organic compounds in aquatic environments.	2007-02-15	17593736
Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBS) in pregnant women from eastern Slovakia.	2007-01	17366814
Intestinal bioavailability and biotransformation of 3,3',4,4'-tetrachlorobiphenyl (CB 77) in in situ preparations of channel catfish following dietary induction of CYP1A.	2006-04-20	16364462
Effects of PCB 52 and PCB 77 on cell viability, [Ca(2+)](i) levels and membrane fluidity in mouse thymocytes.	2006-01-16	16233944
Bioavailability of 2,3',4,4',5-pentachlorobiphenyl (PCB118) and 2,2',5,5'-tetrachlorobiphenyl (PCB52) from soils using a rat model and a physiologically based extraction test.	2006-01-05	16171920
Structure-activity relationship for noncoplanar polychlorinated biphenyl congeners toward the ryanodine receptor-Ca2+ channel complex type 1 (RyR1).	2006-01	16411661
Polychlorinated biphenyls induce arachidonic acid release in human platelets in a tamoxifen sensitive manner via activation of group IVA cytosolic phospholipase A2-alpha.	2005-12-19	16290172
Apoptosis in bovine cumulus-oocyte complexes after exposure to polychlorinated biphenyl mixtures during in vitro maturation.	2005-12	16322545
Occurrence of pesticides, polychlorinated biphenyls (PCBs), and heavy metals in sediments from the Dniester River, Moldova.	2005-11	16132411
Thyroid hormones in pregnancy in relation to environmental exposure to organochlorine compounds and mercury.	2005-08	16079076
Changes in antioxidant defense systems by 2,2',5,5'-tetrachlorobiphenyl exposure in neuronal SK-N-MC cells.	2005-06-17	15837001
CYP35: xenobiotically induced gene expression in the nematode Caenorhabditis elegans.	2005-06-01	15910738
Developmental exposure to low dose PBDE 99: effects on male fertility and neurobehavior in rat offspring.	2005-02	15687051
New passive samplers for chlorinated semivolatile organic pollutants in ambient air.	2005-02	15639256
Effects of PCBs 52 and 77 on Th1/Th2 balance in mouse thymocyte cell cultures.	2005	16435579
Effects of 2,2',5,5'-tetrachlorobiphenyl (PCB52) on migration of chicken primordial germ cells.	2005	15907284
Effects of particulate carbonaceous matter on the bioavailability of benzo[a]pyrene and 2,2',5,5'-tetrachlorobiphenyl to the clam, Macoma balthica.	2004-09-01	15461162

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:58:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:58:30 GMT 2025`
Record UNII	1EH557950R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2,2',5,5'-TCB

Preferred Name

English

2,2',5,5'-TETRACHLOROBIPHENYL

Systematic Name

English

TETRACHLOROBIPHENYL, 2,2',5,5'-

Systematic Name

English

2,5,2',5'-TETRACHLOROBIPHENYL

Systematic Name

English

1,1'-BIPHENYL, 2,2',5,5'-TETRACHLORO-

Systematic Name

English

PCB 52

Common Name

English

Code System Code Type Description

FDA UNII

1EH557950R