ContaminantDB: 2,4-Dichlorophenoxybutyric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2009-06-02 22:18:41 UTC

Update Date

2026-03-27 00:47:58 UTC

Accession Number

CHEM000715

Identification

Common Name

2,4-Dichlorophenoxybutyric acid

Class

Small Molecule

Description

2,4-DB or 4-(2,4-dichlorophenoxy)butyric acid is a selective systemic phenoxy herbicide used to control many annual and perennial broadleaf weeds in alfalfa, peanuts, soybeans, and other crops. Its active metabolite, 2,4-D, inhibits growth at the tips of stems and roots. It is classified in toxicity class III.

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
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-D Butyric acid	ChEBI
4-(2,4-DB)	ChEBI
4-(2,4-Dichlorophenoxy)butyric acid	ChEBI
Butoxone	ChEBI
Butyrac	ChEBI
Embutox	ChEBI
gamma-(2,4-Dichlorophenoxy)-butanoic acid	ChEBI
gamma-(2,4-Dichlorophenoxy)-butyric acid	ChEBI
gamma-(2,4-Dichlorophenoxy)butanoic acid	ChEBI
gamma-(2,4-Dichlorophenoxy)butyric acid	ChEBI
Legumex	ChEBI
2,4-D Butyrate	Generator
4-(2,4-Dichlorophenoxy)butyrate	Generator
g-(2,4-Dichlorophenoxy)-butanoate	Generator
g-(2,4-Dichlorophenoxy)-butanoic acid	Generator
gamma-(2,4-Dichlorophenoxy)-butanoate	Generator
Γ-(2,4-dichlorophenoxy)-butanoate	Generator
Γ-(2,4-dichlorophenoxy)-butanoic acid	Generator
g-(2,4-Dichlorophenoxy)-butyrate	Generator
g-(2,4-Dichlorophenoxy)-butyric acid	Generator
gamma-(2,4-Dichlorophenoxy)-butyrate	Generator
Γ-(2,4-dichlorophenoxy)-butyrate	Generator
Γ-(2,4-dichlorophenoxy)-butyric acid	Generator
g-(2,4-Dichlorophenoxy)butanoate	Generator
g-(2,4-Dichlorophenoxy)butanoic acid	Generator
gamma-(2,4-Dichlorophenoxy)butanoate	Generator
Γ-(2,4-dichlorophenoxy)butanoate	Generator
Γ-(2,4-dichlorophenoxy)butanoic acid	Generator
g-(2,4-Dichlorophenoxy)butyrate	Generator
g-(2,4-Dichlorophenoxy)butyric acid	Generator
gamma-(2,4-Dichlorophenoxy)butyrate	Generator
Γ-(2,4-dichlorophenoxy)butyrate	Generator
Γ-(2,4-dichlorophenoxy)butyric acid	Generator
2,4-Dichlorophenoxybutyrate	Generator
2,4-DB	MeSH
2,4 DM	MeSH
2,4-DM	MeSH
4-(2,4-Dichlorophenoxy)butyric acid, ammonium salt	MeSH
4-(2,4-Dichlorophenoxy)butyric acid, manganese(2+) salt	MeSH
4-(2,4-Dichlorophenoxy)butyric acid, sodium salt	MeSH
4-(2,4-Dichlorophenoxy)butyric acid, copper(2+) salt	MeSH
4-(2,4-Dichlorophenoxy)butyric acid, potassium salt	MeSH

Chemical Formula

C₁₀H₁₀Cl₂O₃

Average Molecular Mass

249.091 g/mol

Monoisotopic Mass

248.001 g/mol

CAS Registry Number

94-82-6

IUPAC Name

4-(2,4-dichlorophenoxy)butanoic acid

Traditional Name

butyrac

SMILES

OC(=O)CCCOC1=CC=C(Cl)C=C1Cl

InChI Identifier

InChI=1S/C10H10Cl2O3/c11-7-3-4-9(8(12)6-7)15-5-1-2-10(13)14/h3-4,6H,1-2,5H2,(H,13,14)

InChI Key

YIVXMZJTEQBPQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
1,3-dichlorobenzene
Alkyl aryl ether
Aryl chloride
Aryl halide
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Organochloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:73173 )
monocarboxylic acid (CHEBI:73173 )
organochlorine compound (CHEBI:73173 )
Phenoxy herbicides (C14404 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

auxin

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	118°C
Boiling Point	Not Available
Solubility	0.046 mg/mL at 25°C [TOMLIN,C (1994)]

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.19	ALOGPS
logP	3.03	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.58	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	5	ChemAxon
Refractivity	57.67 m³·mol⁻¹	ChemAxon
Polarizability	23.48 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-1090000000-de21dab06a16d9dd594d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-5980000000-d0e043f212807520d758	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-4b1c202a64296810a0bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0390000000-bd4c785c99731f0c92b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0950000000-b1a394053669af6dae72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-1900000000-728872f0231b0d0a25fe	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-7900000000-5d6f201d2468101b3001	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Some of the endocrine effects of 2,4-DB may be mediated by the 2,4-D mediated displacement of sex hormones from the sex hormone binding globulin or the 2,4-D mediated blocking or OAT6 transport proteins that are needed for the transport of functional organic ions and dicarboxylates (including estrone sulfate).

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. (3)

Toxicity Values

LD50: 370-700 mg/kg (Oral, Rat); LD50: 2000 mg/kg (Dermal, Rabbit) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (2)

Uses/Sources

Broadleaf herbicide, widely used in agriculture, functions as a synthetic auxin. (3, 4)

Minimum Risk Level

Not Available

Health Effects

All forms of 2,4-DB are considered low in toxicity when absorbed via skin or via inhalation. Female rats fed moderate doses of 75 mg/kg of 2,4-DB, experienced a number of chronic effects including lower ovarian weights, fewer offspring born and lower overall body weight. In addition, numerous offspring (pups) died during lactation.

Symptoms

Symptoms of acute oral exposure include vomiting, diarrhea, headache, confusion, renal failure, aggressive or bizarre behavior, hypotension and muscle twitching. Skeletal muscle injury and renal failure may also occur. Prolonged dermal exposure may include skin irritation, whereas prolonged inhalation exposure may lead to coughing and burning sensations in the upper respiratory tract and chest. (3)

Treatment

The general treatment of acute chlorophenoxy herbicide poisoning consists of decontamination of the gastrointestinal tract, resuscitation and supportive care. For severe, acute oral poisoning by 2,4-DB or 2,4-D, forced alkaline diuresis appears to be most effective (1). Forced alkaline diuresis is often used to increase the excretion of acidic drugs like salicylates and phenobarbitone. For forced alkaline diuresis, a diuretic like furosemide is given intravenously and sodium bicarbonate is added to the infusion fluid to make blood and, in turn, urine alkaline. Potassium replacement becomes of utmost importance during the process because potassium is usually lost in urine. If blood levels of potassium are depleted below normal levels, then hypokalemia occurs, which promotes bicarbonate ion retention and prevents bicarbonate excretion, thus interfering with the alkalinization of the urine.

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

2,4-DB

Chemspider ID

Not Available

ChEBI ID

73173

PubChem Compound ID

1489

Kegg Compound ID

C14404

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

2,4-Dichlorophenoxybutyric acid (CHEM000715)

Structure for CHEM000715: 2,4-Dichlorophenoxybutyric acid