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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
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

PubMed

TitleDatePubMed
Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells.
2000 Apr
Effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on the expression of follicle-stimulating hormone receptors during cell differentiation in cultured granulosa cells.
2000 Apr
TCDD induces CYP1A4 and CYP1A5 in chick liver and kidney and only CYP1A4, an enzyme lacking arachidonic acid epoxygenase activity, in myocardium and vascular endothelium.
2000 Apr 1
Environmental polycyclic aromatic hydrocarbons affect androgen receptor activation in vitro.
2000 Apr 14
Superinduction of CYP1A1 gene expression. Regulation of 2,3,7, 8-tetrachlorodibenzo-p-dioxin-induced degradation of Ah receptor by cycloheximide.
2000 Apr 28
Disruption of dioxin-inducible phase I and phase II gene expression patterns by cadmium, chromium, and arsenic.
2000 Aug
Endocrine disruptive effects of polychlorinated aromatic hydrocarbons on intestinal cholecystokinin in rats.
2000 Aug
TCDD suppression of tissue transglutaminase stimulation by retinoids in malignant human keratinocytes.
2000 Aug
Effect of chlorinated hydrocarbons on expression of cytochrome P450 1A1, 1A2 and 1B1 and 2- and 4-hydroxylation of 17beta-estradiol in female Sprague-Dawley rats.
2000 Aug
Regulation of prostaglandin endoperoxide H synthase-2 induction by dioxin in rat hepatocytes: possible c-Src-mediated pathway.
2000 Dec
2,3,7,8-tetrachlorodibenzo-p-dioxin inhibits luminal cell differentiation and androgen responsiveness of the ventral prostate without inhibiting prostatic 5alpha-dihydrotestosterone formation or testicular androgen production in rat offspring.
2000 Dec
3',4'-dimethoxyflavone as an aryl hydrocarbon receptor antagonist in human breast cancer cells.
2000 Dec
Nonspecific stimulation of the maternal immune system. I. Effects On teratogen-induced fetal malformations.
2000 Dec
NRH:quinone oxidoreductase2 (NQO2).
2000 Dec 1
Effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on the expression of cytochrome P450 1A1, the aryl hydrocarbon receptor, and the aryl hydrocarbon receptor nuclear translocator in rat brain and pituitary.
2000 Dec 1
2,3,7,8-tetrachlorodibenzo-p-dioxin increases serum and kidney retinoic acid levels and kidney retinol esterification in the rat.
2000 Dec 1
The murine IL-2 promoter contains distal regulatory elements responsive to the Ah receptor, a member of the evolutionarily conserved bHLH-PAS transcription factor family.
2000 Dec 15
Molecular characterization and developmental expression of the aryl hydrocarbon receptor from the chick embryo.
2000 Jul
Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes.
2000 Jul 28
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
Generation of alphabeta T-cell receptor+ CD4- CD8+ cells in major histocompatibility complex class I-deficient mice upon activation of the aryl hydrocarbon receptor by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2000 Jun
An aryl hydrocarbon receptor conformation acts as the functional core of nuclear dioxin signaling.
2000 Jun 15
Differential expression of two CYP1A genes in rainbow trout (Oncorhynchys mykiss).
2000 Jun 15
Inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-stimulated Cyp1a1 promoter activity by hypoxic agents.
2000 Jun 15
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) induces binding of a 50 kDa protein on the 3' untranslated region of urokinase-type plasminogen activator mRNA.
2000 Jun 7
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
Nitric oxide inhibits dioxin action for the stimulation of Cyp1a1 promoter activity.
2000 May
Characterization of CYP1A1 and CYP1A3 gene expression in rainbow trout (Oncorhynchus mykiss).
2000 May 1
Diflubenzuron, a benzoyl-urea insecticide, is a potent inhibitor of TCDD-induced CYP1A1 expression in HepG2 cells.
2000 May 1
A novel 4 S [3H]beta-naphthoflavone-binding protein in liver cytosol of female Sprague-Dawley rats treated with aryl hydrocarbon receptor agonists.
2000 May 1
Putative link between transcriptional regulation of IgM expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin and the aryl hydrocarbon receptor/dioxin-responsive enhancer signaling pathway.
2000 Nov
Comparative studies on the effects of green tea extracts and individual tea catechins on human CYP1A gene expression.
2000 Nov 1
Identification and expression of alternatively spliced aryl hydrocarbon nuclear translocator 2 (ARNT2) cDNAs from zebrafish with distinct functions.
2000 Nov 15
Down-regulation of murine Cyp1a-1 in mouse hepatoma Hepa-1c1c7 cells by bisphenol A.
2000 Nov 2
The effects of perinatal exposure to low doses of 2,3,7,8-tetrachlorodibenzo-p-dioxin on immune organs in rats.
2000 Nov 23
Induction of lung lesions in female rats following chronic exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2000 Nov-Dec
Conditional disruption of the aryl hydrocarbon receptor nuclear translocator (Arnt) gene leads to loss of target gene induction by the aryl hydrocarbon receptor and hypoxia-inducible factor 1alpha.
2000 Oct
Inhibition of dioxin effects on bone formation in vitro by a newly described aryl hydrocarbon receptor antagonist, resveratrol.
2000 Oct
Antiestrogenic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin in mouse uterus: critical role of the aryl hydrocarbon receptor in stromal tissue.
2000 Oct
Ovarian tumors in rats induced by chronic 2,3,7,8-tetrachlorodibenzo-p-dioxin treatment.
2000 Oct 1
Hemodynamic dysfunction and cytochrome P4501A mRNA expression induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin during embryonic stages of lake trout development.
2000 Oct 1
The transcriptional signature of dioxin in human hepatoma HepG2 cells.
2000 Oct 15
The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis.
2000 Sep
Dose-response relationships for induction of CYP1A1 and CYP1A2 enzyme activity in liver, lung, and skin in female mice following subchronic exposure to polychlorinated biphenyls.
2000 Sep 15
Aromatic hydrocarbon receptor (AhR).AhR nuclear translocator- and p53-mediated induction of the murine multidrug resistance mdr1 gene by 3-methylcholanthrene and benzo(a)pyrene in hepatoma cells.
2001 Feb 16
7-ketocholesterol is an endogenous modulator for the arylhydrocarbon receptor.
2001 Feb 2
Health risks posed by use of Di-2-ethylhexyl phthalate (DEHP) in PVC medical devices: a critical review.
2001 Jan
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
Organochlorine contaminants and biomarker response in double-crested cormorants nesting in Green Bay and Lake Michigan, Wisconsin, USA.
2001 Jan
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

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
Created
by admin
on Fri Dec 15 17:19:17 UTC 2023
Edited
by admin
on Fri Dec 15 17:19:17 UTC 2023
Record UNII
DO80M48B6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN
HSDB  
Common Name English
DIBENZO(B,E)(1,4)DIOXIN, 2,3,7,8-TETRACHLORO-
Systematic Name English
2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN [HSDB]
Common Name English
TETRACHLORODIBENZO-P-DIOXIN, 2,3,7,8-
Common Name English
D 48
Common Name English
PCDD 48
Common Name English
2,3,7,8-TETRACHLORODIBENZO(B,E)(1,4)DIOXIN
Systematic Name English
2,3,7,8-TCDD
Common Name English
TCDD [MI]
Common Name English
TCDBD
Common Name English
NCI-C03714
Code English
DIOXIN
Systematic Name English
TCDD
MI  
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 600000
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
Code System Code Type Description
PUBCHEM
15625
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
DAILYMED
DO80M48B6O
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
NCI_THESAURUS
C864
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
MERCK INDEX
m10491
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID2021315
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
WIKIPEDIA
2,3,7,8-Tetrachlorodibenzodioxin
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
CHEBI
36682
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
CHEBI
28119
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
CHEBI
134044
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
EVMPD
SUB33620
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
FDA UNII
DO80M48B6O
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
CAS
1746-01-6
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
HSDB
4151
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
217-122-7
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
SMS_ID
100000127538
Created by admin on Fri Dec 15 17:19:17 UTC 2023 , Edited by admin on Fri Dec 15 17:19:17 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT