3,3',4,4',5-pentachlorobiphenyl

Synonyms: "3,4,5,3',4'-pentachlorobiphenyl", "PCB 126", "3,3',4,4',5-pentachloro-1,1'-biphenyl"

Source: 3,3',4,4',5-pentachlorobiphenyl is a member of the polychlorinated biphenyl (PCB), a group of industrial chemicals used as dielectrics, coolants and lubricants in electrical equipment. PCBs contaminate water by leaching from landfills or other waste deposits.

Identifiers:

IUPAC Name: 1,2,3-trichloro-5-(3,4-dichlorophenyl)benzene
CAS Number: 57465-28-8
PubChem ID: 63090
InChiKey: REHONNLQRWTIFF-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=C(C=C1C2=CC(=C(C(=C2)Cl)Cl)Cl)Cl)Cl

Structural Properties:

Molecular Formula: C₁₂H₅Cl₅
Molecular Weight: 326.433

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 0
Number of atoms different from hydrogen: 17

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3D structure (.sdf)
3D structure (.mol2)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Holene E, Nafstad I, Skaare JU, Bernhoft A, Engen P, Sagvolden T. 1995. Behavioral effects of pre- and postnatal exposure to individual polychlorinated biphenyl congeners in rats. Environ Toxicol Chem 14(6):967-976.

Krishnan V, Safe S. 1993. Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), and dibenzofurans (PCDFs) as antiestrogens in MCF-7 human breast cancer cells: quantitative structure-activity relationships. Toxicol Appl Pharmacol 120(1):55-61.

Ramamoorthy K, Gupta MS, Sun G, McDougal A, Safe SH. 1999. 3,3'4,4'-Tetrachlorobiphenyl exhibits antiestrogenic and antitumorigenic activity in the rodent uterus and mammary cells and in human breast cancer cells. Carcinogenesis 20(1):115-123.

Schantz SL, Seo B-W, Moshtaghian J, Amin S. 1997. Developmental exposure to polychlorinated biphenyls or dioxin: do changes in thyroid function mediate effects on spatial learning? Am Zool 37(4):399-408.

Van Birgelen APJM, Smit EA, Kampen IM, Groeneveld CN, Fase KM, Van der Kolk J, Poiger H, Van den Berg M, Koeman JH, Brouwer A. 1995. Subchronic effects of 2,3,7,8-TCDD or PCBs on thyroid hormone metabolism - Use in risk assessment. European Journal of Pharmacology - Environmental Toxicology & Pharmacology Section 293(1):77-85.