Dichloroacetic Acid (CHEM003648)

Record Information
Version1.0
Creation Date2014-09-11 02:05:05 UTC
Update Date2026-08-22 09:32:05 UTC
Accession NumberCHEM003648
Identification
Common NameDichloroacetic Acid
ClassSmall Molecule
Description
Dichloroacetic acid, often abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. The salts and esters of dichloroacetic acid are called dichloroacetates. Salts of DCA are used as drugs since they inhibit the enzyme pyruvate dehydrogenase kinase. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. A phase 1 study in 5 patients concluded that DCA was safe, but wasn't designed to establish effectiveness.
Contaminant Sources
  • Disinfection Byproducts
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Household Toxin
  • Human Neurotoxin
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,2-Dichloroacetic acidChEBI
Bichloracetic acidChEBI
Dichloracetic acidChEBI
DichloressigsaeureChEBI
DICHLORO-acetIC ACIDChEBI
DichloroacetateChEBI
2,2-DichloroacetateGenerator
BichloracetateGenerator
DichloracetateGenerator
DICHLORO-acetateGenerator
Bichloroacetic acidMeSH
Dichloroacetate, potassiumMeSH
Dichloroacetate, sodiumMeSH
Acid, bichloroaceticMeSH
Acid, dichloroaceticMeSH
Potassium dichloroacetateMeSH
Sodium dichloroacetateMeSH
Chemical FormulaC2H2Cl2O2
Average Molecular Mass128.942 g/mol
Monoisotopic Mass127.943 g/mol
CAS Registry Number79-43-6
IUPAC Name2,2-dichloroacetic acid
Traditional Namedichloroacetic acid
SMILESOC(=O)C(Cl)Cl
InChI IdentifierInChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
InChI KeyJXTHNDFMNIQAHM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point13.5°C
Boiling Point194°C
Solubility1E+006 mg/L (at 20°C)
Predicted Properties
PropertyValueSource
Water Solubility72.3 g/LALOGPS
logP0.99ALOGPS
logP1.06ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.62 m³·mol⁻¹ChemAxon
Polarizability9.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureIngestion
Mechanism of ToxicityThe dichloroacetate ion stimulates the activity of the enzyme pyruvate dehydrogenase by inhibiting the enzyme pyruvate dehydrogenase kinase. Thus, it decreases lactate production by shifting the metabolism of pyruvate from fermentation towards oxidation in the mitochondria. (Wikipedia)
MetabolismDichloroacetic acid is metabolized in the liver by oxidative dechlorination to yield glyoxylate, which can enter intermediary metabolism and either be oxidized to oxalate and excreted, converted to carbon dioxide, and/or incorporated into amino acids or other cellular molecules. (3)
Toxicity ValuesORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesDichloroacetic acid has shown promise as a potentially new class of anti-cancer medication, but has yet to complete clinical trials. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. As of October 2014, dichloroacetic acid was undergoing phase III clinical trials for cancer treatment (1) (Wikipedia). Dichloroacetic acid has undergone clinical trials for the treatment of lactic acidosis in humans, but the trials found no clinical benefit (Wikipedia). In 2014 Thomas E. Mallouk and colleagues published a new technique for the production of graphene by intercalation of graphite with non-oxidizing Brønsted acids including dichloroacetic acid, raising the prospect that dichloroacetic acid might be used in industrial graphene production in the future (2).
Minimum Risk LevelNot Available
Health EffectsMultiple independent studies demonstrate that DCA has the ability to alter normal carbohydrate metabolism. Dichloroacetic acid treatment results in a significant reduction in plasma levels of glucose, pyruvate, and lactate. Another consistent finding in DCA ingestion studies is a dose-related increase in liver size, generally accompanied (or caused) by an increase in glycogen deposition in the liver. There is an extensive and consistent data base demonstrating the reproductive toxicity of DCA in males and females. Neurologic symptoms and morphologic changes in the nervous system have been reported in humans, dogs, and rats. (3)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB08809
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-9674
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDichloroacetic_acid
Chemspider IDNot Available
ChEBI ID36386
PubChem Compound ID6597
Kegg Compound IDC11149
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Joanne D. Burger, William L. Howard, “Method for preparing pentachloroacetone and dichloroacetic acid from isopropyl ethers.” U.S. Patent US3996272, issued August, 1968.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24112699