4-hydroxy-2',4',6'-trichlorobiphenyl

Synonyms: "4-hydroxy-2',4',6'-trichlorobiphenyl", "2,4,6-trichloro-4'-biphenylol", "OH-PCB-30", "2',4',6'-trichloro-4-biphenylol", "2',4',6'-trichloro-(1,1'-biphenyl)-4-ol", "4-(2,4,6-trichlorophenyl)phenol", "4'-OH-PCB-30".

Source: 4-hydroxy-2',4',6'-trichlorobiphenyl belongs to the hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs).

Identifiers:

IUPAC Name: 4-(2,4,6-trichlorophenyl)phenol
CAS Number: 14962-28-8
PubChem ID: 105036
InChiKey: LTQJFLVGNGVJCX-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=CC=C1C2=C(C=C(C=C2Cl)Cl)Cl)O

Structural Properties:

Molecular Formula: C₁₂H₇Cl₃O
Molecular Weight: 273.537

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 1
Number of atoms different from hydrogen: 16

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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

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Jin L, Tran DQ, Ide CF, McLachlan JA, Arnold SF. 1997. Several synthetic chemicals inhibit progesterone receptor-mediated transactivation in yeast. Biochemical & Biophysical Research Communications 233(1):139-146. DOI: 10.1006/bbrc.1997.6417. URL: https://www.sciencedirect.com/science/article/pii/S0006291X97964172.
Kester MH, Bulduk S, Tibboel D, Meinl W, Glatt H, Falany CN, Coughtrie MW, Bergman A, Safe SH, Kuiper GG, Schuur AG, Brouwer A, Visser TJ. 2000 . Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology 141(5):1897?1900. DOI: 10.1210/endo.141.5.7530. URL: https://academic.oup.com/endo/article/141/5/1897/2988537.
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. DOI: 10.1016/S0048-9697(99)00221-1. URL: https://www.sciencedirect.com/science/article/pii/S0048969799002211.
Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO. 1995. The E-SCREEN assay as a tool to identify estrogens: An update on estrogenic environmental pollutants. Environ Health Perspect 103 (Suppl. 7):113-122. DOI: 10.2307/3432519 . URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1518887/.