2,3,7,8-tetrachlorodibenzofuran

Synonyms: "TCDBF", "TCDF", "2,3,7,8-TCDF"

Source: 2,3,7,8-tetrachlorodibenzofuran is one of the polychlorinated dibenzofurans (PCDFs), which are ubiquitous environmental contaminants, usually formed as byproducts of the production and use of polychlorinated biphenyls (PCBs). 2,3,7,8-tetrachlorodibenzofuran is also directly released to the environment via emissions from municipal waste incineration, the burning of hazardous waste in industrial boilers, fires involving PCB (polychlorinated biphenyls) transformers, exhaust from automobiles using leaded gasoline, and as a byproduct from the bleaching of pulp.

Identifiers:

IUPAC Name: 2,3,7,8-tetrachlorodibenzofuran
CAS Number: 51207-31-9
PubChem ID: 39929
InChiKey: KSMVNVHUTQZITP-UHFFFAOYSA-N
Canonical SMILES: C1=C2C3=CC(=C(C=C3OC2=CC(=C1Cl)Cl)Cl)Cl

Structural Properties:

Molecular Formula: C₁₂H₄Cl₄O
Molecular Weight: 305.972

Pharmacophore Features:

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

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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

Bandiera S, Sawyer T, Romkes M, Zmudzka B, Safe L, Mason G, Keys B, Safe S. 1984. Polychlorinated dibenzofurans (PCDFs): effects of structure on binding to the 2,3,7,8-TCDD cytosolic receptor protein, AHH induction and toxicity. Toxicology 32(2):131-144.

Gierthy JF, Lincoln DW, Gillespie MB, Seeger JI, Martinez HI, Dickerman HW, Kumar SA. 1987. Suppression of estrogen-regulated extracellular tissue plasminogen activator activity of MCF-7 cells by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cancer Res 47(23):6198-6203.

Harper N, Wang X, Liu H, Safe S. 1994. Inhibition of estrogen-induced progesterone receptor in MCF-7 human breast cancer cells by aryl hydrocarbon (Ah) receptor agonists. Molecular & Cellular Endocrinology 104(1):47-55.

Mason G, Sawyer T, Keys B, Bandiera S, Romkes M, Piskorska-Pliszczynska J, Zmudzka B, Safe S. 1985. Polychlorinated dibenzofurans (PCDFs): correlation between in vivo and in vitro structure-activity relationships. Toxicology 37(1-2):1-12.