2-Methyl-4-chlorophenoxyacetic acid (CHEM000717)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-06-02 22:22:59 UTC
Update Date2016-11-09 01:08:21 UTC
Accession NumberCHEM000717
Identification
Common Name2-Methyl-4-chlorophenoxyacetic acid
ClassSmall Molecule
Description2-methyl-4-chlorophenoxyacetic acid or MCPA is a powerful, selective, widely used phenoxy herbicide. It controls broadleaf weeds, including thistle and dock, in cereal crops and pasture. It is selective for plants with broad leaves, and this includes most deciduous trees. Clovers are tolerant at moderate application levels. It is currently classified as a restricted use pesticide in the United States.
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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
((4-Chloro-O-tolyl)oxy)acetic acidChEBI
(2-Methyl-4-chlorophenoxy)acetic acidChEBI
2,4-MCPAChEBI
2-Methyl-4-chlorphenoxyessigsaeureChEBI
[(4-Chloro-O-tolyl)oxy]acetic acidChEBI
AgroxoneChEBI
MCPChEBI
MCPAChEBI
((4-Chloro-O-tolyl)oxy)acetateGenerator
(2-Methyl-4-chlorophenoxy)acetateGenerator
[(4-Chloro-O-tolyl)oxy]acetateGenerator
2-Methyl-4-chlorophenoxyacetateGenerator
MethoxoneMeSH
2 Methyl 4 chlorophenoxyacetic acidMeSH
Chemical FormulaC9H9ClO3
Average Molecular Mass200.619 g/mol
Monoisotopic Mass200.024 g/mol
CAS Registry Number94-74-6
IUPAC Name2-(4-chloro-2-methylphenoxy)acetic acid
Traditional Namezelan
SMILESCC1=CC(Cl)=CC=C1OCC(O)=O
InChI IdentifierInChI=1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)
InChI KeyWHKUVVPPKQRRBV-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
  • Toluene
  • 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 Point120°C
Boiling PointNot Available
Solubility0.63 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP2.41ALOGPS
logP2.41ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability19.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5910000000-860ca41c738b41f7b504Spectrum
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 - 60V, Negativesplash10-0006-0900000000-ff229e048896cb82eea8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-0900000000-17d15181eb2b419433e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-0900000000-2ea18be66a01057572e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-0900000000-4075a19636afe9c55f70Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0005-0900000000-e70d941bd3d16b1a9f72Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-795ed8a189928639332eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-7eb0c60951b148ac7643Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-b6fd64e83a2ef8f9f587Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-0900000000-f8b486493ca73907b87dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-43bf20d21e9cd16dedf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-48b5c0927cd1bec5e6b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-0900000000-18b0498fb0604b831b99Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-d470f18c127833c5c28eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-7e7c62ac5d04fe45fd2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0002-0900000000-6b72ca1fdd5e73f53870Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-3a1ceb59eb92c79ea962Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0005-0900000000-cab6faf69b70080c6b15Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-70c39f43575e12567240Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-adfde0044cfc6ea40a2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1690000000-f8cc589fb93acc1df5ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3900000000-466950da4a977e9d5021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-47df881008b2c5f12517Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-4bf18997df6aa7f82e4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-64c749464336695fcb87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-cc9acefac078097ce3baSpectrum
MSMass Spectrum (Electron Ionization)splash10-0f96-7930000000-6ca0a096b6e50d7722b1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C 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 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 LinkMCPA
Chemspider IDNot Available
ChEBI ID50099
PubChem Compound ID7204
Kegg Compound IDC18528
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15669026