2,3,7,8-tetrachlorodibenzo-p-dioxin

Synonyms: "tetrachlorodibenzodioxin", "tetradioxin", "dioxin", "dioxine", "2,3,7,8-tetrachlorooxanthrene", "TCDD", "TCDBD"

Source: 2,3,7,8-tetrachlorodibenzodioxin is the most potent compound of its series (dioxins) and became known as a contaminant in Agent Orange, a herbicide used in the Vietnam War.

Identifiers:

IUPAC Name: 2,3,7,8-tetrachlorodibenzo-p-dioxin
CAS Number: 1746-01-6
PubChem ID: 15625
InChiKey: HGUFODBRKLSHSI-UHFFFAOYSA-N
Canonical SMILES: C1=C2C(=CC(=C1Cl)Cl)OC3=CC(=C(C=C3O2)Cl)Cl

Structural Properties:

Molecular Formula: C₁₂H₄Cl₄O₂
Molecular Weight: 321.971

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 0
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

Hojo R, Zareba G, Kai JW, Baggs RB, Weiss B. 2006. Sex-specific alterations of cerebral cortical cell size in rats exposed prenatally to dioxin. J Appl Toxicol 26(1):25-34.

Jablonska O, Piasecka J, Petroff BK, Nynca A, Siawrys G, Wasowska B, Zmijewska A, Lewczuk B, Ciereszko RE. 2011. In vitro effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on ovarian, pituitary, and pineal function in pigs. Theriogenology 76(5):921-932.

Kurita H, Yoshioka W, Nishimura N, Kubota N, Kadowaki T, Tohyama C. 2009. Aryl hydrocarbon receptor-mediated effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on glucose-stimulated insulin secretion in mice. J Appl Toxicol 29(8):689-694.

Nishimura N, Yonemoto J, Miyabara Y, Fujii-Kuriyama Y, Tohyama C. 2005. Altered thyroxin and retinoid metabolic response to 2,3,7,8-tetrachlorodibenzo-p-dioxin in aryl hydrocarbon receptor- mice. Arch Toxicol 79(5):260-267.

Shi ZQ, Valdez KE, Ting AY, Franczak A, Gum SL, Petroff BK. 2007. Ovarian endocrine disruption underlies premature reproductive senescence following environmentally relevant chronic exposure to the aryl hydrocarbon receptor agonist 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biol Reprod 76(2):198-202.