2,3,7,8-Tetrachlorodibenzodioxin
| 2,3,7,8-Tetrachlorodibenzodioxin | |
|---|---|
| File:Dioxin-2D-skeletal.svg | |
| File:Dioxin-3D-vdW.png | |
| 2,3,7,8-Tetrachlorooxanthrene | |
| Other names Tetradioxin; Tetrachlorodibenzodioxin; Tetrachlorodibenzo-p-dioxin | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| Abbreviations | TCDD; TCDBD |
| CAS number | 1746-01-6 
|
| PubChem | 15625 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C12H4Cl4O2 |
| Molar mass | 321.97 g/mol |
| Density | 1.8 g cm−3 |
| Melting point |
305 °C, 578 K, 581 °F |
| log P | 6.8 |
| Vapor pressure | 1.5 × 10−9 mmHg |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
2,3,7,8-Tetrachlorodibenzodioxin (TCDD) is a polychlorinated dibenzodioxin (dioxin). It is the most potent compound of the series and became known as a contaminant in Agent Orange, an herbicide used in the Vietnam War.[1]
Contents
Mechanism of action
It is not considered to be directly genotoxic, but potentially causing indirect DNA damage through induction or activation of other DNA damaging compounds in the body. Other mechanisms include oxidative stress and endocrine disruption.[2] The endocrine disrupting activities seem to be dependent on life stage, being anti-estrogenic when estrogen is present (or in high concentration) in the body, and estrogenic in the absence of estrogen.[2] In 1997 it was classified by the International Agency for Research on Cancer as a carcinogen for humans (group 1).[3]
Viktor Yushchenko poisoning
TCDD was used in the poisoning of Ukranian President Viktor Yushchenko in 2004. TCDD levels in his blood serum were 50,000-fold greater than those in the general population.[4]
See Also
- Polychlorinated dibenzodioxins
- Agent Orange
- Seveso disaster
- List of IARC Group 1 carcinogens
- Chloracne
References
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<references />, or <references group="..." />External links
- U.S. National Library of Medicine: ChemIDplus - 2,3,7,8-Tetrachlorodibenzodioxin
- U.S. National Library of Medicine: Hazardous Substances Databank – 2,3,7,8-Tetrachlorodibenzodioxin
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de:2,3,7,8-Tetrachlordibenzodioxin fr:2,3,7,8-tétrachlorodibenzo-p-dioxine gl:TCDD it:TCDD nl:2,3,7,8-tetrachloordibenzo-p-dioxine pl:TCDD (chemia) pt:TCDD
sv:2,3,7,8-Tetraklordibenso-p-dioxin- ↑ Schecter A, Birnbaum L, Ryan JJ, Constable JD (2006). "Dioxins: an overview". Environ. Res. 101 (3): 419–28. doi:10.1016/j.envres.2005.12.003. PMID 16445906.
- ↑ 2.0 2.1 Cancer incidence in the population exposed to dioxin after the "Seveso accident": twenty years of follow-up. Angela Cecilia Pesatori, Dario Consonni, Maurizia Rubagotti, Paolo Grillo and Pier Alberto Bertazz Environmental Health 2009, 8:39 doi:10.1186/1476-069X-8-39. Published: 15 September 2009
- ↑ International Agency for Research on Cancer (IARC). Monographs on the Evaluation of Carcinogenic Risks to Humans, vol. 69, Polychlorinated dibenzo-para-dioxins and polychlorinated dibenzofurans, 1997, Lyon, IARC
- ↑ Sorg, R.; Zennegg, M.; Schmid, P.; Fedosyuk, R; Valikhnovskyi, R.; Gaide, O.; Kniazevych, V.; Saurat, J.-H. (2009). "2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) poisoning in Victor Yushchenko: identification and measurement of TCDD metabolites". The Lancet. 374 (9696): 1179–1185. doi:10.1016/S0140-6736(09)60912-0. More than one of
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