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style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
Abbreviations TCDD; TCDBD
CAS number 1746-01-6 YesY
PubChem 15625
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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
 YesY (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]

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


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External links


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

  1. 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. 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
  3. 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
  4. 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 |first1= and |first= specified (help)