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
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
Molecular Formula | C12H4Cl4O2 |
Molecular Weight | 321.971 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
Title | Date | PubMed |
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Quantitative analysis of constitutive and 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1B1 expression in human lymphocytes. | 1999 Feb |
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Aryl hydrocarbon receptor imported into the nucleus following ligand binding is rapidly degraded via the cytosplasmic proteasome following nuclear export. | 1999 Oct 1 |
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Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition. | 1999 Sep |
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Endocrine disruptive effects of polychlorinated aromatic hydrocarbons on intestinal cholecystokinin in rats. | 2000 Aug |
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TCDD suppression of tissue transglutaminase stimulation by retinoids in malignant human keratinocytes. | 2000 Aug |
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NRH:quinone oxidoreductase2 (NQO2). | 2000 Dec 1 |
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Acute administration of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in pregnant Long Evans rats: association of measured tissue concentrations with developmental effects. | 2000 Feb |
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Serum alters the uptake and relative potencies of halogenated aromatic hydrocarbons in cell culture bioassays. | 2000 Feb |
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Demonstration of 2,3,7,8-tetrachlorodibenzo-p-dioxin attenuation of P450 steroidogenic enzyme mRNAs in rat granulosa cell in vitro by competitive reverse transcriptase-polymerase chain reaction assay. | 2000 Jun |
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Inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-stimulated Cyp1a1 promoter activity by hypoxic agents. | 2000 Jun 15 |
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Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice. | 2000 Mar 15 |
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Inhibition of dioxin effects on bone formation in vitro by a newly described aryl hydrocarbon receptor antagonist, resveratrol. | 2000 Oct |
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Ovarian tumors in rats induced by chronic 2,3,7,8-tetrachlorodibenzo-p-dioxin treatment. | 2000 Oct 1 |
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The transcriptional signature of dioxin in human hepatoma HepG2 cells. | 2000 Oct 15 |
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Serum levels of TCDD and dioxin-like chemicals in Rhesus monkeys chronically exposed to dioxin: correlation of increased serum PCB levels with endometriosis. | 2001 Jan |
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Anti-CD40 Treatment of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-exposed C57Bl/6 mice induces activation of antigen presenting cells yet fails to overcome TCDD-induced suppression of allograft immunity. | 2001 Jan 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8917677
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792845
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
Created
by
admin
on
Edited
Mon Mar 31 18:44:30 GMT 2025
by
admin
on
Mon Mar 31 18:44:30 GMT 2025
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Record UNII |
DO80M48B6O
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Record Status |
Validated (UNII)
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Record Version |
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EPA PESTICIDE CODE |
600000
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2,3,7,8-Tetrachlorodibenzodioxin
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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