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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-13 11:39:50 UTC
Update Date2021-10-13 08:36:51 UTC
HMDB IDHMDB0041797
Secondary Accession Numbers
  • HMDB41797
Metabolite Identification
Common Name2,4-Dichlorophenoxyacetic acid
Description2,4-D is a member of the phenoxy family of herbicides, which include:; 2,4-D is a synthetic auxin, which is a class of plant hormones. It is absorbed through the leaves and is translocated to the meristems of the plant. Uncontrolled, unsustainable growth ensues, causing stem curl-over, leaf withering, and eventual plant death. 2,4-D is typically applied as an amine salt, but more potent ester versions exist as well. 2,4-Dichlorophenoxyacetic acid (usually referred to by its abbreviation, 2,4-D) is a common systemic pesticide/herbicide used in the control of broadleaf weeds. It is one of the most widely used herbicide in the world, and the third most commonly used in North America. 2,4-D is a synthetic auxin (plant hormone), and as such it is often used in laboratories for plant research and as a supplement in plant cell culture media such as MS medium. It was a major ingredient in Agent Orange alongside its chemically similar relative, 2,4,5-T (2,4,5-trichlorophenoxyacetic acid).
Structure
Thumb
Synonyms
Chemical FormulaC8H6Cl2O3
Average Molecular Weight221.037
Monoisotopic Molecular Weight219.969399472
IUPAC Name2-(2,4-dichlorophenoxy)acetic acid
Traditional Namerhodia
CAS Registry Number94-75-7
SMILES
OC(=O)COC1=C(Cl)C=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12)
InChI KeyOVSKIKFHRZPJSS-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentChlorophenoxyacetates
Alternative Parents
Substituents
  • Chlorophenoxyacetate
  • Phenoxy compound
  • 1,3-dichlorobenzene
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140.5 °CNot Available
Boiling Point345.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.68 mg/mL at 25 °CNot Available
LogP2.81Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000116 (0.0000962-0.000140) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.000165 (0.000127-0.000215) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111663
KNApSAcK IDNot Available
Chemspider ID1441
KEGG Compound IDC03664
BioCyc IDCPD-9009
BiGG IDNot Available
Wikipedia Link2,4-Dichlorophenoxyacetic_acid
METLIN IDNot Available
PubChem Compound1486
PDB IDCFA
ChEBI ID28854
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029790
Good Scents IDrw1163761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available