ContaminantDB: Methylchlorophenoxypropionic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-02 22:33:20 UTC

Update Date

2026-03-25 19:45:07 UTC

Accession Number

CHEM000719

Identification

Common Name

Methylchlorophenoxypropionic acid

Class

Small Molecule

Description

Mecoprop, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(4-Chloro-2-methylphenoxy)propionic acid	ChEBI
2-(4-Chloro-2-tolyloxy)propionic acid	ChEBI
2-(p-Chloro-O-tolyloxy)propionic acid	ChEBI
4-Chloro-2-methylphenoxy-alpha-propionic acid	ChEBI
Mecoprop	ChEBI
O-(4-Chloro-2-methylphenyl)lactic acid	ChEBI
2-(4-Chloro-2-methylphenoxy)propionate	Generator
2-(4-Chloro-2-tolyloxy)propionate	Generator
2-(p-Chloro-O-tolyloxy)propionate	Generator
4-Chloro-2-methylphenoxy-a-propionate	Generator
4-Chloro-2-methylphenoxy-a-propionic acid	Generator
4-Chloro-2-methylphenoxy-alpha-propionate	Generator
4-Chloro-2-methylphenoxy-α-propionate	Generator
4-Chloro-2-methylphenoxy-α-propionic acid	Generator
O-(4-Chloro-2-methylphenyl)lactate	Generator
Methylchlorophenoxypropionate	Generator
Mecoprop, potassium salt	MeSH
Mecoprop, potassium salt, (+-)-isomer	MeSH
Mecoprop, sodium salt, (+-)-isomer	MeSH
Mecoprop, (R)-isomer	MeSH
Mecoprop, ammonium salt	MeSH
2-Methyl-4-chlorophenoxypropionic acid	MeSH
Mecoprop, (+-)-isomer	MeSH
Mecoprop, (S)-isomer	MeSH
Mecoprop, sodium salt	MeSH

Chemical Formula

C₁₀H₁₁ClO₃

Average Molecular Mass

214.646 g/mol

Monoisotopic Mass

214.040 g/mol

CAS Registry Number

93-65-2

IUPAC Name

2-(4-chloro-2-methylphenoxy)propanoic acid

Traditional Name

mecoprop

SMILES

CC(OC1=CC=C(Cl)C=C1C)C(O)=O

InChI Identifier

InChI=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 Key

WNTGYJSOUMFZEP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

2-phenoxypropionic acids

Direct Parent

2-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:75704 )
monocarboxylic acid (CHEBI:75704 )
monochlorobenzenes (CHEBI:75704 )
Phenoxy herbicides (C18742 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

herbicide

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	94.5°C
Boiling Point	Not Available
Solubility	0.62 mg/mL at 20°C [MARTIN,H & WORTHING,CR (1977)]

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	2.87	ALOGPS
logP	2.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.95 m³·mol⁻¹	ChemAxon
Polarizability	20.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1900000000-ac5895b5fc793274272e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-0900000000-11480ccdc682acf643a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-0900000000-35ac6c6fa42b085bff76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0900000000-a5fe008b371ac3a09068	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-01ox-0940000000-d67151b96f4db9b5c8fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-0900000000-7c2c26ebad0bbc389d73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-0900000000-78fe325c97eeb615bb6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-0900000000-d1d892cf06b30e189f20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-0900000000-f13d6ff14498342f7f7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-0900000000-cc43b19d54523b6fdb91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-01ox-0940000000-1991429b9e6b1d34daf3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-0900000000-bb036567f924f1bfd16f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-0900000000-3ea2459793789ac2ab76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0006-0900000000-4075a19636afe9c55f70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0006-0900000000-ff229e048896cb82eea8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1980000000-8c7b5fb29aab1f034b32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-2910000000-832e0bf62c4c2e533d5d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-3900000000-5181e68db5f5e77a3c05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0290000000-8bd0d82fa7cbbb521f18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-0930000000-d64f57906ccd7632a322	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-1900000000-32d683cd7014a51a8388	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-0920000000-3ebee7efd38e453bedba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-0900000000-11415a668ebe7ae530dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9800000000-49b96972eeb200dc85ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2920000000-143d9ac5b3dca1a57235	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-64d108b3e48a8092bcb9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-4910000000-7bdfa1d9086c4836e053	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

CDDs 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)

Metabolism

CDDs 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (4)

Uses/Sources

Dioxins 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 Level

Not Available

Health Effects

Exposure 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)

Symptoms

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (1)

Treatment

Treatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Mecoprop

Chemspider ID

Not Available

ChEBI ID

75704

PubChem Compound ID

7153

Kegg Compound ID

C18742

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Methylchlorophenoxypropionic acid (CHEM000719)

Structure for CHEM000719: Methylchlorophenoxypropionic acid