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Details

Stereochemistry ACHIRAL
Molecular Formula C12H4Cl4O2
Molecular Weight 321.971
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN

SMILES

ClC1=CC2=C(OC3=CC(Cl)=C(Cl)C=C3O2)C=C1Cl

InChI

InChIKey=HGUFODBRKLSHSI-UHFFFAOYSA-N
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H

HIDE SMILES / InChI

Molecular Formula C12H4Cl4O2
Molecular Weight 321.971
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

2,3,7,8-Tetrachlorodibenzo-p-dioxin which is often referred to simply as dioxin and is the reference for a number of compounds which are similar structurally and have dioxin-like toxicity. A substance extremely toxic to mammals, with a wide variation in sensitivity among species. Longer-term exposure of test mammals to lesser amounts can affect reproduction, cause birth defects, damage the liver and suppress the immune system. Several studies suggest that exposure to TCDD increases the risk of several types of cancer in people. Animal studies have also shown an increased risk of cancer from exposure to TCDD. The WHO and the USA DHHS have determined that TCDD is a human carcinogen. TCDD is a persistent environmental contaminant inadvertently produced as a by-product of herbicide and pesticide manufacturing. TCDD is also released during the bleaching process at tree pulp and paper mills, and during burning of municipal solid waste. Dioxins, like TCDD, have a long environmental half-life, bioaccumulate in the food chain, and can be found in human fat tissue, blood serum, breast milk and ovarian follicular fluid. TCDD is an aryl hydrocarbon receptor (AhR) agonist

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Treatment of pregnant female Sprague-Dawley rats on Gestational Day 15 with a single oral dose of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) (0.5, 1.0, or 2.0 ug/kg) or indole-3-carbinol (I3C, 1.0 or 100 mg/kg), an aryl hydrocarbon (Ah) receptor agonist which is found in cruciferous vegetables, resulted in reproductive abnormalities in the male offspring (three to five litters in each treatment group).
Route of Administration: Oral
In Vitro Use Guide
Treatment of rat hippocampal neuronal cultures with 2,3,7,8-TCDD (10-100 nM) resulted in a rapid concentration-dependent increase in [Ca2+]i associated with a decrease in mitochondrial membrane potential and activation of alpha-protein kinase C (alpha-PKC).
Substance Class Chemical
Record UNII
DO80M48B6O
Record Status Validated (UNII)
Record Version