4,4'-dihydroxy-3,3',5,5'-tetrachlorobiphenyl

Synonyms: "3,3',5,5'-tetrachloro-4,4'-biphenyldiol ", "2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenyl)phenol"

Source: 4,4'-dihydroxy-3,3',5,5'-tetrachlorobiphenyl is a hydroxylated polychlorinated biphenyl (OH-PCB). OH-PCBs are metabolites of PCBs (polychlorinated biphenyls), which are widely used as dielectric and coolant fluids.

Identifiers:

IUPAC Name: 2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenyl)phenol
CAS Number: 13049-13-3
PubChem ID: 97032
InChiKey: YCYDXOVJXVALHY-UHFFFAOYSA-N
Canonical SMILES: C1=C(C=C(C(=C1Cl)O)Cl)C2=CC(=C(C(=C2)Cl)O)Cl

Structural Properties:

Molecular Formula: C₁₂H₆Cl₄O₂
Molecular Weight: 323.987

Pharmacophore Features:

Number of bond donors: 2
Number of bond acceptors: 2
Number of atoms different from hydrogen: 18

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2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM. 2000. The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol Sci 54(1):138-153.

Cheek AO, Kow K, Chen J, McLachlan JA. 1999. Potential mechanisms of thyroid disruption in humans: Interaction of organochlorine compounds with thyroid receptor, transthyretin, and thyroid-binding globulin. Environ Health Perspect 107(4):273-278.

Korach KS, Sarver P, Chae K, McLachlan JA, McKinney JD. 1988. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Mol Pharmacol 33(1):120-126.

Kramer VJ, Giesy JP. 1999. Specific binding of hydroxylated polychlorinated biphenyl metabolites and other substances to bovine calf uterine estrogen receptor: structure-binding relationships. Sci Total Environ 233(1-3):141-161.