ChemFOnt: Showing chemical card for (4-Chloro-2-methylphenoxy)acetic acid (CFc000233891)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:04:18 UTC

Chemfont ID

CFc000233891

Molecule Identification

Common Name

(4-Chloro-2-methylphenoxy)acetic acid

Definition

2-Methyl-4-chlorophenoxyacetic acid, also known as 2,4-mcpa or agroxone, 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. 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. 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-Methyl-4-chlorophenoxyacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methyl-4-chlorophenoxyacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. The affinity for the Ah receptor depends on the structure of the specific CDD. Clovers are tolerant at moderate application levels. Treatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
((4-Chloro-O-tolyl)oxy)acetic acid	ChEBI
(2-Methyl-4-chlorophenoxy)acetic acid	ChEBI
2,4-MCPA	ChEBI
2-Methyl-4-chlorphenoxyessigsaeure	ChEBI
[(4-Chloro-O-tolyl)oxy]acetic acid	ChEBI
Agroxone	ChEBI
MCP	ChEBI
MCPA	ChEBI
((4-Chloro-O-tolyl)oxy)acetate	Generator
(2-Methyl-4-chlorophenoxy)acetate	Generator
[(4-Chloro-O-tolyl)oxy]acetate	Generator
2-Methyl-4-chlorophenoxyacetate	Generator
Methoxone	MeSH
2 Methyl 4 chlorophenoxyacetic acid	MeSH

Chemical Formula

C₉H₉ClO₃

Average Molecular Weight

200.619

Monoisotopic Molecular Weight

200.024021861

IUPAC Name

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

Traditional Name

zelan

CAS Registry Number

94-74-6

SMILES

CC1=CC(Cl)=CC=C1OCC(O)=O

InChI Identifier

InChI=1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)

InChI Key

WHKUVVPPKQRRBV-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Chlorophenoxyacetates

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:50099 )
chlorophenoxyacetic acid (CHEBI:50099 )
Phenoxy herbicides (C18528 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.41	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.36	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	48.45 m³·mol⁻¹	ChemAxon
Polarizability	19.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MCPA

METLIN ID

Not Available

PubChem Compound

7204

PDB ID

Not Available

ChEBI ID

50099

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (4-Chloro-2-methylphenoxy)acetic acid (CFc000233891)

MOL for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

3D MOL for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

3D SDF for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

3D-SDF for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

PDB for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

3D PDB for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

SMILES for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

INCHI for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

Structure for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)

3D Structure for CFc000233891 ((4-Chloro-2-methylphenoxy)acetic acid)