Methylchlorophenoxypropionic acid (CHEM000719)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-02 22:33:20 UTC
Update Date2016-10-28 10:04:03 UTC
Accession NumberCHEM000719
Identification
Common NameMethylchlorophenoxypropionic acid
ClassSmall Molecule
DescriptionMecoprop, or methylchlorophenoxypropionic acid (MCPP), is a common general use herbicide found in many household weed killers and weed-and-feed type lawn fertilizers. It is primarily used to control broadleaf weeds. It is often used in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA.The United States Environmental Protection Agency has classified mecoprop as toxicity class III - slightly toxic. Mecoprop is a mixture of two stereoisomers, with the (R)-(+)-enantiomer ('Mecoprop-P', 'Duplosan KV') possessing the herbicidal activity
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(4-Chloro-2-methylphenoxy)propionic acidChEBI
2-(4-Chloro-2-tolyloxy)propionic acidChEBI
2-(p-Chloro-O-tolyloxy)propionic acidChEBI
4-Chloro-2-methylphenoxy-alpha-propionic acidChEBI
MecopropChEBI
O-(4-Chloro-2-methylphenyl)lactic acidChEBI
2-(4-Chloro-2-methylphenoxy)propionateGenerator
2-(4-Chloro-2-tolyloxy)propionateGenerator
2-(p-Chloro-O-tolyloxy)propionateGenerator
4-Chloro-2-methylphenoxy-a-propionateGenerator
4-Chloro-2-methylphenoxy-a-propionic acidGenerator
4-Chloro-2-methylphenoxy-alpha-propionateGenerator
4-Chloro-2-methylphenoxy-α-propionateGenerator
4-Chloro-2-methylphenoxy-α-propionic acidGenerator
O-(4-Chloro-2-methylphenyl)lactateGenerator
MethylchlorophenoxypropionateGenerator
Mecoprop, potassium saltMeSH
Mecoprop, potassium salt, (+-)-isomerMeSH
Mecoprop, sodium salt, (+-)-isomerMeSH
Mecoprop, (R)-isomerMeSH
Mecoprop, ammonium saltMeSH
2-Methyl-4-chlorophenoxypropionic acidMeSH
Mecoprop, (+-)-isomerMeSH
Mecoprop, (S)-isomerMeSH
Mecoprop, sodium saltMeSH
Chemical FormulaC10H11ClO3
Average Molecular Mass214.646 g/mol
Monoisotopic Mass214.040 g/mol
CAS Registry Number93-65-2
IUPAC Name2-(4-chloro-2-methylphenoxy)propanoic acid
Traditional Namemecoprop
SMILESCC(OC1=CC=C(Cl)C=C1C)C(O)=O
InChI IdentifierInChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)
InChI KeyWNTGYJSOUMFZEP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub Class2-phenoxypropionic acids
Direct Parent2-phenoxypropionic acids
Alternative Parents
Substituents
  • 2-phenoxypropionic acid
  • Phenoxyacetate
  • 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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point94.5°C
Boiling PointNot Available
Solubility0.62 mg/mL at 20°C [MARTIN,H & WORTHING,CR (1977)]
Predicted Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP2.87ALOGPS
logP2.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.95 m³·mol⁻¹ChemAxon
Polarizability20.78 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, Positivesplash10-0006-1900000000-ac5895b5fc793274272eSpectrum
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 - 90V, Negativesplash10-0006-0900000000-11480ccdc682acf643a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-35ac6c6fa42b085bff76Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-a5fe008b371ac3a09068Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-01ox-0940000000-d67151b96f4db9b5c8feSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-7c2c26ebad0bbc389d73Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-0900000000-78fe325c97eeb615bb6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0900000000-d1d892cf06b30e189f20Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0006-0900000000-f13d6ff14498342f7f7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0006-0900000000-cc43b19d54523b6fdb91Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-01ox-0940000000-1991429b9e6b1d34daf3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0900000000-bb036567f924f1bfd16fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-3ea2459793789ac2ab76Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-4075a19636afe9c55f70Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-ff229e048896cb82eea8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1980000000-8c7b5fb29aab1f034b32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-2910000000-832e0bf62c4c2e533d5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-3900000000-5181e68db5f5e77a3c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-8bd0d82fa7cbbb521f18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0930000000-d64f57906ccd7632a322Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-1900000000-32d683cd7014a51a8388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-0920000000-3ebee7efd38e453bedbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0900000000-11415a668ebe7ae530ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9800000000-49b96972eeb200dc85efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2920000000-143d9ac5b3dca1a57235Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-64d108b3e48a8092bcb9Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-4910000000-7bdfa1d9086c4836e053Spectrum
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 LinkMecoprop
Chemspider IDNot Available
ChEBI ID75704
PubChem Compound ID7153
Kegg Compound IDC18742
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available