ContaminantDB: 1,2,3,6,8-Pentachlorodibenzo-p-dioxin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-06-24 17:37:28 UTC

Update Date

2016-11-09 01:08:37 UTC

Accession Number

CHEM001844

Identification

Common Name

1,2,3,6,8-Pentachlorodibenzo-p-dioxin

Class

Small Molecule

Description

1,2,3,6,8-Pentachlorodibenzo-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
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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₁₂H₃Cl₅O₂

Average Molecular Mass

356.416 g/mol

Monoisotopic Mass

353.858 g/mol

CAS Registry Number

71925-16-1

IUPAC Name

1,2,3,6,8-pentachlorooxanthrene

Traditional Name

1,2,3,6,8-pentachlorooxanthrene

SMILES

ClC1=CC(Cl)=C2OC3=CC(Cl)=C(Cl)C(Cl)=C3OC2=C1

InChI Identifier

InChI=1S/C12H3Cl5O2/c13-4-1-6(15)11-7(2-4)19-12-8(18-11)3-5(14)9(16)10(12)17/h1-3H

InChI Key

VKDGHBBUEIIEHL-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxins

Sub Class

Benzo-p-dioxins

Direct Parent

Chlorinated 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	7.06	ALOGPS
logP	6.02	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-9.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.51 m³·mol⁻¹	ChemAxon
Polarizability	30.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-a979278bc1bad0d1a2bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0009000000-a979278bc1bad0d1a2bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0009000000-a979278bc1bad0d1a2bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-890ad09a0ddb04e4c565	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-905926a77e0ae1a84694	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uec-4069000000-1846ccc28af9e7ee14d6	Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ; inhalation(3) ; dermal (3)

Mechanism of Toxicity

CDDs 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)

Metabolism

CDDs 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (2)

Uses/Sources

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)

Minimum Risk Level

Acute Oral: 0.0002 ug/kg/day (1) Intermediate Oral: 0.00002 ug/kg/day (1) Chronic Oral: 0.000001 ug/kg/day (1)

Health Effects

Exposure 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)

Symptoms

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (3)

Treatment

Treatment of CDD exposure may include washing the area of contact, GI decontamination, administering an IV, or forced alkaline diuresis. (5)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

51455

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

1,2,3,6,8-Pentachlorodibenzo-p-dioxin (CHEM001844)

Structure for CHEM001844: 1,2,3,6,8-Pentachlorodibenzo-p-dioxin