1,2,3,4-Tetrachlorodibenzo-p-dioxin (CHEM001815)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-06-24 17:37:22 UTC
Update Date2016-11-09 01:08:37 UTC
Accession NumberCHEM001815
Identification
Common Name1,2,3,4-Tetrachlorodibenzo-p-dioxin
ClassSmall Molecule
Description1,2,3,4-Tetrachlorodibenzo-p-dioxin is one of 75 chlorinated dibenzo-p-dioxin (CDD) congeners. CDDs are a class of manufactured chemicals that consist of dioxin skeletel structures with chlorine substituents. They are also persistent organic pollutants (POPs), thus their production is regulated in most areas. Dioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (3, 4)
Contaminant Sources
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • Sludge Chemicals
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Chlorinated Dibenzo-p-dioxin
  • Ether
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-TCDDChEBI
1,2,3,4-Tetrachlorodibenzo-p-dioxinChEBI
1,2,3,4-Tetrachlorodibenzo-para-dioxinChEBI
1,2,3,4-Tetrachlorodibenzo[b,e][1,4]dioxinChEBI
1,2,3,4-TetrachlorodibenzodioxinChEBI
Chemical FormulaC12H4Cl4O2
Average Molecular Mass321.971 g/mol
Monoisotopic Mass319.897 g/mol
CAS Registry Number30746-58-8
IUPAC Name1,2,3,4-tetrachlorooxanthrene
Traditional Name1,2,3,4-tetrachlorooxanthrene
SMILESClC1=C(Cl)C(Cl)=C2OC3=CC=CC=C3OC2=C1Cl
InChI IdentifierInChI=1S/C12H4Cl4O2/c13-7-8(14)10(16)12-11(9(7)15)17-5-3-1-2-4-6(5)18-12/h1-4H
InChI KeyDJHHDLMTUOLVHY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorinated dibenzo-p-dioxins. These are organic compounds containing a chlorine atom attached to a dibenzo-p-dioxin moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxins
Sub ClassBenzo-p-dioxins
Direct ParentChlorinated dibenzo-p-dioxins
Alternative Parents
Substituents
  • Chlorinated-dibenzo-p-dioxin
  • Diaryl ether
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point188°C
Boiling PointNot Available
Solubility6.3e-07 mg/mL at 25°C [SHIU,WY et al. (1988)]
Predicted Properties
PropertyValueSource
Water Solubility0.00046 g/LALOGPS
logP6.55ALOGPS
logP5.42ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-9.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.7 m³·mol⁻¹ChemAxon
Polarizability28.1 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1029000000-632075fc8878509b5944Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-dd099c2bb1cc795b3df6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-dd099c2bb1cc795b3df6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-8009000000-17992bce6b3308c993deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-76f693f852ade3315761Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-76f693f852ade3315761Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-5029000000-4a7acfa90bf63942633eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-4dbeba209253cb5483a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-4dbeba209253cb5483a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0029000000-1ab59199c34764e5699cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-1baa921818929ae5c9abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-1baa921818929ae5c9abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0059000000-663495e7520c44944d19Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5439000000-2bcd4629c63987fdd4a6Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation(3) ; dermal (3)
Mechanism of ToxicityCDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (3)
MetabolismCDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (2)
Uses/SourcesDioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (3, 4)
Minimum Risk LevelAcute Oral: 0.0002 ug/kg/day (1) Intermediate Oral: 0.00002 ug/kg/day (1) Chronic Oral: 0.000001 ug/kg/day (1)
Health EffectsExposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (3, 4)
SymptomsIn addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (3)
TreatmentTreatment of CDD exposure may include washing the area of contact, GI decontamination, administering an IV, or forced alkaline diuresis. (5)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID32611
ChEBI ID27785
PubChem Compound IDNot Available
Kegg Compound IDC11058
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available