ContaminantDB: Dichloroacetic Acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:05 UTC

Update Date

2016-10-28 10:01:07 UTC

Accession Number

CHEM003648

Identification

Common Name

Dichloroacetic Acid

Class

Small 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abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms.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
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dichloroacetic acid	ChEBI
Bichloracetic acid	ChEBI
Dichloracetic acid	ChEBI
Dichloressigsaeure	ChEBI
DICHLORO-acetIC ACID	ChEBI
Dichloroacetate	ChEBI
2,2-Dichloroacetate	Generator
Bichloracetate	Generator
Dichloracetate	Generator
DICHLORO-acetate	Generator
Bichloroacetic acid	MeSH
Dichloroacetate, potassium	MeSH
Dichloroacetate, sodium	MeSH
Acid, bichloroacetic	MeSH
Acid, dichloroacetic	MeSH
Potassium dichloroacetate	MeSH
Sodium dichloroacetate	MeSH

Chemical Formula

C₂H₂Cl₂O₂

Average Molecular Mass

128.942 g/mol

Monoisotopic Mass

127.943 g/mol

CAS Registry Number

79-43-6

IUPAC Name

2,2-dichloroacetic acid

Traditional Name

dichloroacetic acid

SMILES

OC(=O)C(Cl)Cl

InChI Identifier

InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)

InChI Key

JXTHNDFMNIQAHM-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-halocarboxylic acids and derivatives

Direct Parent

Alpha-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 Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:36386 )
organochlorine compound (CHEBI:36386 )
Halogenated fatty acids (LMFA01090070 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	13.5°C
Boiling Point	194°C
Solubility	1E+006 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	72.3 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.06	ChemAxon
logS	-0.25	ALOGPS
pKa (Strongest Acidic)	2.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	22.62 m³·mol⁻¹	ChemAxon
Polarizability	9.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-6900000000-9d33b2f109bd8208b818	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-cdde3faa793ecb51af1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-c1ded91474fde2787d95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0019-9000000000-cea4fe3c3f1653aa150d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-68d75216c4534c61a4b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0059-6900000000-55338ed4fe8335b6f8ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-d0c2081f59cf4a1d9bb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-aa8cfce9c157e8ce5c26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0019-9000000000-d0fd266005ba1e11af9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-67e8e2a12579c484a9d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2c591b536e9b1cdd5103	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-e235e740081767bebeb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ec-7900000000-19ec9f5725beb405a85f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-9824d7737d8edd5c640c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1900000000-047b42b607987ffb5cba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-d56ccde35fe241d821f6	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-5cc2c87638085fad9afc	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion

Mechanism of Toxicity

The 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)

Metabolism

Dichloroacetic 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 Values

ORAL (LD50): Acute: 2820 mg/kg [Rat]; DERMAL (LD50): Acute: 510 mg/kg [Rabbit]

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (4)

Uses/Sources

Dichloroacetic 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 Level

Not Available

Health Effects

Multiple 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)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB08809

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-9674

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dichloroacetic_acid

Chemspider ID

Not Available

ChEBI ID

36386

PubChem Compound ID

6597

Kegg Compound ID

C11149

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24112699

Dichloroacetic Acid (CHEM003648)

Structure for CHEM003648: Dichloroacetic Acid