pentachlorophenol

Synonyms: "chlorophen", "lauxtol", "pentachlorophenate", "dowicide 7", "2,3,4,5,6-pentachlorophenol", "fungifen", "liroprem"

Source: pentachlorophenol is a manufactured chemical which is a restricted use pesticide and is used industrially as a wood preservative for utility poles, railroad ties, and wharf pilings.

Identifiers:

IUPAC Name: 2,3,4,5,6-pentachlorophenol
CAS Number: 87-86-5
PubChem ID: 992
InChiKey: IZUPBVBPLAPZRR-UHFFFAOYSA-N
Canonical SMILES: C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)O

Structural Properties:

Molecular Formula: C₆HCl₅O
Molecular Weight: 266.337

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 1
Number of atoms different from hydrogen: 12

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

Danzo BJ. 1997. Environmental xenobiotics may disrupt normal endocrine function by interfering with the binding of physiological ligands to steroid receptors and binding proteins. Environ Health Perspect 105(3):294-301.

McConnell EE, Huff JE, Hejtmancik M, Peters AC, Persing R. 1991. Toxicology and carcinogenesis studies of two grades of pentachlorophenol in B6C3F1 mice. Fundam Appl Toxicol 17(3):519-532.

Rawlings NC, Cook SJ, Waldbillig D. 1998. Effects of the pesticides carbofuran, chlorpyrifos, dimethoate, lindane, triallate, trifluralin, 2,4-D, and pentachlorophenol on the metabolic endocrine and reproductive endocrine system in ewes. J Toxicol Environ Health 54(1):21-36.

Tran DQ, Klotz DM, Ladlie BL, Ide CF, McLachlan JA, Arnold SF. 1996. Inhibition of progesterone receptor activity in yeast by synthetic chemicals. Biochem Biophys Res Commun 229(2):518-523.

van den Berg KJ. 1990. Interaction of chlorinated phenols with thyroxine binding sites of human transthyretin, albumin and thyroid binding globulin. Chem Biol Interact 76(1):63-75.