2,3,5,6-Tetrachlorophenol (T3D0870)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-06-15 17:20:33 UTC
Update Date2014-12-24 20:22:54 UTC
Accession NumberT3D0870
Identification
Common Name2,3,5,6-Tetrachlorophenol
ClassSmall Molecule
Description2,3,5,6-Tetrachlorophenol is a biodegradation product of polychlorinated benzene and polychlorinated biphenols.
Compound Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2,3,5, 6-Tetrachlorophenol
2,3,5,6-Tetrachloro phenol
2,3,5,6-Tetrachlorophenate
2,3,5,6-Tetrachlorophenol solution
WLN: QR bg CG eg FG
Chemical FormulaC6H2Cl4O
Average Molecular Mass231.891 g/mol
Monoisotopic Mass229.886 g/mol
CAS Registry Number935-95-5
IUPAC Name2,3,5,6-tetrachlorophenol
Traditional Name2,3,5,6-tetrachlorophenol
SMILESOC1=C(Cl)C(Cl)=CC(Cl)=C1Cl
InChI IdentifierInChI=1S/C6H2Cl4O/c7-2-1-3(8)5(10)6(11)4(2)9/h1,11H
InChI KeyInChIKey=KEWNKZNZRIAIAK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-chlorophenols. These are chlorophenols carrying a iodine at the C2 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassHalophenols
Direct ParentO-chlorophenols
Alternative Parents
Substituents
  • 2-chlorophenol
  • 3-chlorophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point115°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.099 g/LALOGPS
logP4.45ALOGPS
logP4.09ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)5.25ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.26 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2022-08-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-48c0be405602c36c15262016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-e538b04aa45113cfaff12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-0970000000-f2a72c45f0df9c0d74cf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-08217b277413993527c92016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-4c84de79bc4bbc2eca0a2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-0960000000-450f19d37b47584e56dd2016-06-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-4690000000-d32a2509948e346356362014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.53 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureInhalation (5) ; oral (5) ; dermal (5) ; eye contact (5)
Mechanism of Toxicity2,3,5,6-tetrachlorophenol acts at the sites of adenosine triphosphate production and decreases or blocks it without blocking the electron transport chain. Thus the poison uncouples phosphorylation from oxidation. Free energy from the electron transport chain then converts to more body heat. As body temp rises, heat-dissipating mechanisms are overcome and metabolism is speeded. More adenosine diphosphate and other substrates accumulate, and these substrates stimulate the electron transport chain further. The electron transport chain responds by using up more and more available oxygen (increasing oxygen demand) in an effort to produce adenosine triphosphate, but much of the free energy generated is liberated as still more body heat. Oxygen demand quickly overcomes oxygen supply, and energy reserves become depleted (1).
Metabolism2,3,5,6-Tetrachlorophenol is rapidly absorbed and excreted following occupational exposure, which involves both the inhalation and dermal routes. Sulfation and glucuronidation are the main metabolic pathways of 2,3,5,6-tetrachlorophenol. Studies suggest rapid absorption after dermal application. 2,3,5,6-Tetrachlorophenol is excreted as tetrachloro-p-hydroquinone, and partly unchanged (5).
Toxicity ValuesLD50: 89 mg/kg (Oral, Mouse) (5) LD50: >2000 mg/kg (Dermal, Rabbit) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not directly listed by IARC, but related polychlorophenols are discussed, and combined exposures to polychlorophenols or to their sodium salts are classified as possibly carcinogenic to humans (Group 2B). (4)
Uses/SourcesBreathing contamiated air; drinking contaminated water; eating contaminating food; skin/eye contact (particularly while treating wood) (5).
Minimum Risk LevelNot Available
Health EffectsDermal exposure can cause corrosive skin damage (5).
SymptomsDust has been found irritating to the nose and throat. Skin or eye contact can cause irritation of the exposed surface. Clinical signs preceding death for all tetrachlorophenol isomers included initial hyperactivity followed by hypoactivity, neuromuscular weakness, and convulsions. Headache can also result from exposure to 2,3,5,6-tetrachlorophenol (5).
TreatmentIn case of oral exposure, dilution may enhance absorption of phenol, and should be avoided; charcoal may be administered. If methemoglobinemia occurs, administer 1 to 2 mg/kg of 1% methylene blue slowly IV in symptomatic patients. Additional doses may be required. if hypotensin occurs, infuse 10 to 20 mL/kg isotonic fluid. If hypotension persists, administer dopamine or norepinephrine. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress, and if cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes following eye exposure. Following dermal exposure, remove phenol with undiluted polyethylene glycol 300 to 400 or isopropyl alcohol prior to washing, if readily available. Wash exposed areas twice or for at least 10 minutes with large quantities of soapy water. Water alone may be harmful. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID13636
ChEMBL IDCHEMBL1606550
ChemSpider ID13047
KEGG IDC15505
UniProt IDNot Available
OMIM ID
ChEBI ID52048
BioCyc IDDIHYDRO-DIOH-BENZOATE
CTD IDC039673
Stitch ID2,3,5,6-Tetrachlorophenol
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Huq MD, Tsai NP, Gupta P, Wei LN: Regulation of retinal dehydrogenases and retinoic acid synthesis by cholesterol metabolites. EMBO J. 2006 Jul 12;25(13):3203-13. Epub 2006 Jun 8. [16763553 ]
  2. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  3. Booth, NH, McDonald LE (eds) (1982). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press.
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for chlorophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. ATP synthase subunit alpha, mitochondrial
General Function:
Transmembrane transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Subunits alpha and beta form the catalytic core in F(1). Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits. Subunit alpha does not bear the catalytic high-affinity ATP-binding sites (By similarity).
Gene Name:
ATP5A1
Uniprot ID:
P25705
Molecular Weight:
59750.06 Da
References
  1. Janik F, Wolf HU: The Ca(2+)-transport-ATPase of human erythrocytes as an in vitro toxicity test system--acute effects of some chlorinated compounds. J Appl Toxicol. 1992 Oct;12(5):351-8. [1447481 ]
Target Details
2. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]