2,4,4',5-Tetrachlorobiphenyl - 32690-93-0

2,4,4',5-Tetrachlorobiphenyl

Catalog Number: EVT-293184
CAS Number: 32690-93-0
Molecular Formula: C12H6Cl4
Molecular Weight: 292 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description

Polychlorinated biphenyls (PCBs) are a group of synthetic organic chemicals that consist of 209 individual chlorinated compounds, known as congeners. These compounds have been widely used in various industrial applications due to their chemical stability and insulating properties. However, their persistence in the environment and potential for bioaccumulation and toxicity have raised significant environmental health concerns. Among the PCBs, 2,2',5,5'-tetrachlorobiphenyl is a lightly chlorinated ortho-substituted congener that has been the subject of various studies to understand its biological effects and mechanisms of action12.

Mechanism of Action

The biological activity of 2,2',5,5'-tetrachlorobiphenyl and its metabolites has been investigated in several assays. Studies have shown that this congener does not induce lung adenomas in A/J mice or skin papillomas in SENCAR mice, indicating a lack of activity in these tumor induction and promotion assays. However, it has been observed to have promoting activity for hepatic gamma-glutamyl transpeptidase-positive foci in rat liver when initiated by diethylnitrosamine, with the 2,2',4,4'-tetrachlorobiphenyl isomer exhibiting approximately 10-fold greater promoting activity1. Additionally, neonatal exposure to 2,2',5,5'-tetrachlorobiphenyl has been linked to increased susceptibility in the cholinergic transmitter system at adult age, particularly affecting the cholinergic nicotinic receptors in the cerebral cortex and altering the response to cholinergic agents like nicotine2. Furthermore, the metabolism of this congener leads to the formation of mono- and bis-methyl sulphone metabolites, which show a selective affinity for lung and kidney tissues in mice4.

Applications in Various Fields

The study of 2,2',5,5'-tetrachlorobiphenyl and its derivatives has implications in various fields, including environmental science, toxicology, and pharmacology. For instance, the induction of rat liver microsomal cytochrome P-450 isozymes and epoxide hydrolase by 4'-substituted-2,3,4,5-tetrachlorobiphenyls has provided insights into the molecular mechanisms of enzyme induction and the role of structural characteristics of PCBs in receptor binding and enzyme induction3. In environmental health, understanding the metabolism and tissue distribution of PCBs, such as the identification of hydroxylated urinary metabolites in rabbits, is crucial for assessing the risks associated with exposure to these compounds5. These studies contribute to the development of better risk assessment models and the design of strategies for the remediation of PCB-contaminated sites.

Properties

CAS Number

32690-93-0

Product Name

2,4,4',5-Tetrachlorobiphenyl

IUPAC Name

1,2,4-trichloro-5-(4-chlorophenyl)benzene

Molecular Formula

C12H6Cl4

Molecular Weight

292 g/mol

InChI

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

InChI Key

TULCXSBAPHCWCF-UHFFFAOYSA-N

SMILES

C1=CC(=CC=C1C2=CC(=C(C=C2Cl)Cl)Cl)Cl

Solubility

1.70e-08 M

Synonyms

2,4,4',5-tetrachlorobiphenyl
PCB 74
PCB-74
PCB74 cpd

Canonical SMILES

C1=CC(=CC=C1C2=CC(=C(C=C2Cl)Cl)Cl)Cl

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