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Record Information
Version2.0
Creation Date2009-06-02 22:33:20 UTC
Update Date2014-12-24 20:22:51 UTC
Accession NumberT3D0806
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
Compound Type
  • Aromatic Hydrocarbon
  • Ether
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+ )-a-(4-chloro-2-Methylphenoxy) propionic acid
(+)-.alpha.-(4-chloro-2-methylphenoxy) propionic acid
(+)-a-(4-chloro-2-Methylphenoxy) propionic acid
(+)-alpha-(4-chloro-2-Methylphenoxy) propionic acid
(+-)-2-((4-chloro-O-Tolyl)oxy)propionic acid
(4-chloro-2-Methylphenoxy)propionic acid
2-(2'-Methyl-4'-chlorophenoxy)propionic acid
2-(2-Methyl-4-chlorophenoxy)propionic acid
2-(4-Chloor-2-methyl-fenoxy)-propionzuur
2-(4-Chlor-2-methyl-phenoxy)-propionsaeure
2-(4-chloro-2-Methylphenoxy)propanoic acid
2-(4-chloro-2-Methylphenoxy)propionic acid
2-(4-chloro-2-Tolyloxy)propionic acid
2-(4-chloro-O-Tolyl)oxylpropionic acid
2-(4-chloro-O-Tolyloxy)propionic acid
2-(4-Chlorophenoxy-2-methyl)propionic acid
2-(P-chloro-O-Tolyloxy)propionic acid
2-MCPP
2-Methyl-4-chlorophenoxy-.alpha.-propionic acid
2-Methyl-4-chlorophenoxy-a-propionic acid
4-chloro-2-Methylphenoxy-.alpha.-propionic acid
4-chloro-2-Methylphenoxy-a-propionic acid
4-chloro-2-Methylphenoxy-alpha-propionic acid
a-(2-Methyl-4-chlorophenoxy)propionic acid
a-(4-chloro-2-Methylphenoxy)propionic acid
alpha-(2-Methyl-4-chlorophenoxy)propionic acid
Alpha.-(2-methyl-4-chlorophenoxy)propionic acid
Anicon b
Anicon p
Astix
BH mecoprop
Caswell No. 559
Celatox CMPP
Chipco turf herbicide MCPP
CMPP
Compitox
Duplosan CMPP
Duplosan new system CMPP
FBC CMPP
Hedonal
Hedonal MCPP
Iso-cornox
Isocarnox
Kilprop
Liranox
MCPP
MCPP 2,4-D
MCPP-D-4
MCPP-K-4
Mechlorprop
Mecomec
Mecopar
Mecopeop
Mecoper
Mecopex
Mecoprop
Mecoprop-p
Mecoturf
Mecprop
Mepro
Methoxone
Methylchlorophenoxypropionate
Morogal
Mwcoprop
N.b. mecoprop
O-(4-chloro-2-Methylphenyl)lactic acid
Propionic acid, 2-(4-chloro-2-methylphenoxy)
Propionic acid, {2-[(4-chloro-O-tolyl)oxy]-}
Proponex-plus
Rankotex
Runcatex
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 KeyInChIKey=WNTGYJSOUMFZEP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.727 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.95 m3·mol-1ChemAxon
Polarizability20.78 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1980000000-8c7b5fb29aab1f034b32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-2910000000-832e0bf62c4c2e533d5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-3900000000-5181e68db5f5e77a3c05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-8bd0d82fa7cbbb521f18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0930000000-d64f57906ccd7632a322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-1900000000-32d683cd7014a51a8388View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-4910000000-7bdfa1d9086c4836e053View in MoNA
1D NMR13C NMR SpectrumNot Available
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID7153
ChEMBL IDCHEMBL272942
ChemSpider ID6886
KEGG IDC18742
UniProt IDNot Available
OMIM ID
ChEBI ID75704
BioCyc IDCPD0-1524
CTD IDC008340
Stitch IDMethylchlorophenoxypropionic acid
PDB IDNot Available
ACToR ID6483
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for chlorinated dibenzo-p-dioxins (CDDs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. Polychlorinated dibenzodioxins. Last Updated 19 May 2009. [Link]
  3. US Environmental Protection Agency (2009). Recognition and Management of Pesticide Poisonings. [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for chlorinated dibenzo-p-dioxins (CDDs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]