2,4,5-Trichlorophenoxyacetic acid (CHEM000716)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-02 22:20:30 UTC
Update Date2016-11-09 01:08:21 UTC
Accession NumberCHEM000716
Identification
Common Name2,4,5-Trichlorophenoxyacetic acid
ClassSmall Molecule
Description2,4,5-Trichlorophenoxyacetic acid (also known as 2,4,5-T), a synthetic auxin, is a chlorophenoxy acetic acid herbicide used to defoliate broad-leafed plants. It was developed in the late 1940s and was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns. Human health effects from 2,4,5-T at low environmental doses or at biomonitored levels from low environmental exposures are unknown. Intentional overdoses and unintentional high dose occupational exposures to chlorophenoxy acid herbicides have resulted in weakness, headache, dizziness, nausea, abdominal pain, myotonia, hypotension, renal and hepatic injury, and delayed neuropathy. IARC considers the chlorophenoxyacetic acids group of chemicals as possibly carcinogenic to humans.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2,4,5-Trichlorphenoxy)essigsaeureChEBI
2,4,5-TChEBI
2,4,5-TrichlorphenoxyessigsaeureChEBI
Esteron 245ChEBI
TrioxoneChEBI
2,4,5-TrichlorophenoxyacetateGenerator
Chemical FormulaC8H5Cl3O3
Average Molecular Mass255.483 g/mol
Monoisotopic Mass253.930 g/mol
CAS Registry Number93-76-5
IUPAC Name2-(2,4,5-trichlorophenoxy)acetic acid
Traditional Namefortex
SMILESOC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl
InChI IdentifierInChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13)
InChI KeySMYMJHWAQXWPDB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentChlorophenoxyacetates
Alternative Parents
Substituents
  • Chlorophenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organochloride
  • Hydrocarbon derivative
  • 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
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point153°C
Boiling PointNot Available
Solubility0.278 mg/mL at 25°C [HARTLEY,D & KIDD,H (1983)]
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP3.44ALOGPS
logP3.11ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.02 m³·mol⁻¹ChemAxon
Polarizability21.51 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066u-5590000000-339b8d2afea784290252Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-0dba2270e5b005cb1fa5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-e70cd03a25074dc69a97Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-3bd420d6bb10a80c15e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-47cc371a40d0fca5004bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-a291236dc12637727caaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-052f-0900000000-38d0639b572bbc345ee3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052f-0900000000-166d89a52ec7e4e6a5cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-022bb350e5597754eaddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0090000000-fab7dcfce398fcd73aeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-4980000000-e3bbb539bae44c823682Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-ea3c32f50b94ea7ce51eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-497e12d49508588a6bbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-0390000000-321b1df17ed37a468342Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0090000000-b48edbb25901d18f8832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-0090000000-87821c239c34a6002abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0590000000-9f5f70b08a4de3081334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-b5425e36fe41f17309b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-6090000000-f960c6f8f87d5eb4bad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-71763a4dd38f109889d9Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-2940000000-9383d1cf77861ad29badSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
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. This includes 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes. (1)
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 CDDs induce both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
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. (1, 2)
Minimum Risk LevelNot Available
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. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known human carcinogen. (1, 2)
SymptomsIn addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (1)
TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0245475
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-10896
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2,4,5-Trichlorophenoxyacetic_acid
Chemspider ID1435
ChEBI ID27903
PubChem Compound ID1480
Kegg Compound IDC07100
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23085749
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23167922
3. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.