1-Chlorodibenzo-p-dioxin (CHEM001789)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-06-24 17:37:18 UTC
Update Date2016-11-09 01:08:37 UTC
Accession NumberCHEM001789
Identification
Common Name1-Chlorodibenzo-p-dioxin
ClassSmall Molecule
Description1-Chlorodibenzo-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
  • 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-chloro-dibenzo[14]DioxineChEMBL
PCDDMeSH
polychlorodibenzo-4-DioxinMeSH
polychlorodibenzo-P-DioxinMeSH
Polychlorinated dibenzodioxinMeSH
2,3,7,8-Tetrachlorodibenzo-p-dioxinMeSH
Chlorinated dibenzo p dioxinsMeSH
Chlorinated dibenzo-p-dioxinsMeSH
Polychlorinated dibenzo-p-dioxinsMeSH
Polychlorodibenzo 4 dioxinMeSH
Dibenzodioxin, polychlorinatedMeSH
TCDDMeSH
Tetrachlorodibenzo-p-dioxinMeSH
Dibenzo-p-dioxins, chlorinatedMeSH
Dibenzo-p-dioxins, polychlorinatedMeSH
Dibenzodioxins, polychlorinatedMeSH
Polychlorinated dibenzo p dioxinsMeSH
Polychlorinated dibenzodioxinsMeSH
Tetrachlorodibenzo p dioxinMeSH
Polychlorodibenzo p dioxinMeSH
TetrachlorodibenzodioxinMeSH
Chemical FormulaC12H7ClO2
Average Molecular Mass218.636 g/mol
Monoisotopic Mass218.013 g/mol
CAS Registry Number39227-53-7
IUPAC Name1-chlorooxanthrene
Traditional Name1-chlorodibenzo-P-dioxin
SMILESClC1=CC=CC2=C1OC1=CC=CC=C1O2
InChI IdentifierInChI=1S/C12H7ClO2/c13-8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H
InChI KeyVGGGRWRBGXENKI-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 DescriptorsNot Available
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 Point104.5°C
Boiling PointNot Available
Solubility0.000417 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.96ALOGPS
logP3.6ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57.29 m³·mol⁻¹ChemAxon
Polarizability21.37 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3970000000-6f9eb1c47e07ce8abab5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-8651a543fb27d884f351Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-c11c59699cd6da36fd11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9060000000-b21c05e2162d2b241d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a03dcf2da1cd56983f26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-9578bbbfbb2a3f12e42bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nb-9740000000-4e00385744f45d2b0a19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-ac03f37b7d82207a4616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-ac03f37b7d82207a4616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0940000000-d672334e1f033fb1056fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-65c4916db7f7e002b9d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-65c4916db7f7e002b9d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1790000000-2c8b60b1706741c2619dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0v6r-9240000000-99c34b26c4e3918a7d0bSpectrum
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 IDHMDB0243849
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 ID34148
ChEBI IDNot Available
PubChem Compound ID37207
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available