Trichloroacetic acid (CED0000967)

Record Information
Version1.0
Creation Date2014-09-11 05:20:07 UTC
Update Date2026-08-22 10:01:57 UTC
Accession NumberCHEM003826
Identification
Common NameTrichloroacetic acid
ClassSmall Molecule
Description
Trichloroacetic acid (C2HCl3O2) is an exogenous organic compound with an average molecular weight of 163.39 g/mol. It exists as a solid at room temperature and is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Trichloroacetic acid belongs to the alpha-halocarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. Biologically, the compound is used as a herbicide (PMC10343502) and targets the oxysterols receptor LXR-alpha (NR1H3). Health effects associated with the compound include major depressive disorder (PMC11187323) and a decrease in cancer (PMC5297775). Trichloroacetic acid has been released from 44 recorded sources across several sectors. These include aquatic systems and sediments, such as seawater, freshwater, surface water, and groundwater; drinking water and water supply, including bottled, tap, and desalinated water; and wastewater, sanitation and biosolids, such as mine wastewater, industrial wastewater, and wastewater treatment effluent. It is also found in household cleaning and consumer products, including tobacco pipes, soap detergents, and perfumes within detergents and soaps. Additionally, it is linked to food, food processing and cookware, including food preservation, food contact materials, and fermentation processes for beer, as well as the preparation of vinegar and wine or sparkling wine. It is further associated with electrical and electronic equipment, such as contacts, electric switches, discharge lamps, conductors or conductive bodies characterised by the conductive materials, and antennas. Recorded exposure routes for the compound include touch, oral, and inhalation.
Contaminant Type
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • PMT
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
TCAChEBI
Trichloracetic acidChEBI
TrichloressigsaeureChEBI
Trichloroethanoic acidChEBI
TrichloroacetateKegg
Acido tricloroaceticoKegg
TrichloracetateGenerator
TrichloroethanoateGenerator
2,2,2-Trichloro-acetic acidHMDB
Acetic acid, trichloro- (solid)HMDB
Aceto-caustinHMDB
Acide trichloracetiqueHMDB
Amchem grass killerHMDB
CCL3coohHMDB
KonestaHMDB
Kyselina trichloroctovaHMDB
TKhUHMDB
TKhUKHMDB
TrichloorazijnzuurHMDB
TrichloressigsaureHMDB
Trichloro-acetic acidHMDB
Trichloroacetic acid (acd/name 4.0)HMDB
Trichloroacetic acid solid (dot)HMDB
Trichloroacetic acid solution (dot)HMDB
Trichloroacetate, rubidiumHMDB
Sodium trichloroacetateHMDB
Trichloracetique, acideHMDB
Rubidium trichloroacetateHMDB
Acid, trichloroaceticHMDB
Sanofi brand OF trichloroacetic acidHMDB
Trichloroacetate, sodiumHMDB
Chemical FormulaC2HCl3O2
Average Molecular Mass163.387 g/mol
Monoisotopic Mass161.904 g/mol
CAS Registry Number76-03-9
IUPAC Nametrichloroacetic acid
Traditional Nametrichloroacetic acid
SMILESOC(=O)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
InChI KeyYNJBWRMUSHSURL-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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point57.5 °C
Boiling Point195.5°C (383.9°F)
Solubility44 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility2.12 g/LALOGPS
logP1.17ALOGPS
logP1.53ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.16 m³·mol⁻¹ChemAxon
Polarizability11.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0296-4900000000-7ca41d8f0edd786c2b1cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00xr-9620000000-7ddd39e1ab7e71700aabNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-2a1f08f2f9f0958b82bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-63726390145b4934cc07Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0296-5900000000-c47c1239bda29fa232bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-3b15586f346ff06bc481Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-1fc541b5cac29990c848Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-4cf63adcb5470ed26fddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-37c55a7d3f64d0228a3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-37c55a7d3f64d0228a3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2900000000-7849c6c36f8a17868f0fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-4aa5094ff4be0f74cd97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-4aa5094ff4be0f74cd97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-4aa5094ff4be0f74cd97Not AvailableView Spectrum
MSMS Spectrumsplash10-001j-9000000000-b5749368152821947a2bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2545.0Log mg/kg[1400:4500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
cancerassociated_withdecreasePMC5297775
major depressive disorderassociated_withNot AvailablePMC11187323
cholangiocarcinomaelevated_in_blood_inincreasePMC7399932
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
233BrushesPersonal care & cosmeticsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureType IV secretion-like conjugative transfer relaxase protein TraIB1LRJ1Escherichia coli (strain SMS-3-5 / SECEC)Predicted (SEA)0.0778492
Click to view 3D structureFumarate hydratase, mitochondrialP10173Sus scrofaPredicted (SEA)0.544945
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)3004.2
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)4.43741
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)16.4262
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)19.7737
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)1873.36
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)4389.29
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)25.3788
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)518.32
Click to view 3D structureExcitatory amino acid transporter 3P51907Rattus norvegicusPredicted (SEA)33.9423
Click to view 3D structureInward rectifier potassium channel 2P35561Mus musculusPredicted (SEA)1012.74
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)6583.24
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)6038.45
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)6337.0
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)55.8179
Click to view 3D structureSodium- and chloride-dependent betaine transporterP48065HumansPredicted (SEA)34.0201
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)5798.29
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)5045.8
Metabotropic glutamate receptor 2 structureClick to view 3D structureMetabotropic glutamate receptor 2Q14416HumansPredicted (SEA)5355.33
Click to view 3D structureGlutamate receptor ionotropic, NMDA 1P35439Rattus norvegicusPredicted (SEA)919.399
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)5594.87
Metabotropic glutamate receptor 1 structureClick to view 3D structureMetabotropic glutamate receptor 1Q13255HumansPredicted (SEA)5087.45
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)5879.56
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)3836.41
Oxysterols receptor LXR-alpha structureClick to view 3D structureOxysterols receptor LXR-alphaQ13133HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDBSALT001528
HMDB IDHMDB0042048
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-9675
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrichloroacetic_Acid
Chemspider ID10772050
ChEBI ID30956
PubChem Compound ID6421
Kegg Compound IDC11150
YMDB IDNot Available
ECMDB IDM2MDB004925
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12573897
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16298895
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16815816
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16901594
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21269351
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21332915
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21457391
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21497335
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21523508
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21529453
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21549800
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21716542
13. Song Y, Chidan Kumar CS, Akkurt M, Chandraju S, Li H: 1-[(4-Chloro-phen-yl)(phen-yl)meth-yl]piperazine-1,4-diium bis-(trichloro-acetate)-trichloro-acetic acid (1/1). Acta Crystallogr Sect E Struct Rep Online. 2012 Sep 1;68(Pt 9):o2695-6. doi: 10.1107/S1600536812034794. Epub 2012 Aug 11.
14. Husek P, Svagera Z, Hanzlikova D, Simek P: Survey of several methods deproteinizing human plasma before and within the chloroformate-mediated treatment of amino/carboxylic acids quantitated by gas chromatography. J Pharm Biomed Anal. 2012 Aug-Sep;67-68:159-62. doi: 10.1016/j.jpba.2012.04.027. Epub 2012 May 7.
15. Arjunan V, Marchewka MK, Pietraszko A, Kalaivani M: X-ray diffraction, vibrational and quantum chemical investigations of 2-methyl-4-nitroanilinium trichloroacetate trichloroacetic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:625-38. doi: 10.1016/j.saa.2012.07.018. Epub 2012 Jul 16.
16. Valencia DP, Astudillo PD, Galano A, Gonzalez FJ: Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions. Org Biomol Chem. 2013 Jan 14;11(2):318-25. doi: 10.1039/c2ob26961a. Epub 2012 Nov 19.