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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:22 UTC
Update Date2018-03-12 22:08:18 UTC
HMDB IDHMDB0031331
Secondary Accession Numbers
  • HMDB31331
Metabolite Identification
Common NameChloroacetic acid
DescriptionProhibited from use in food Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. Like other chloroacetic acids and related halocarbons, it is a potentially dangerous alkylating agent
Structure
Thumb
Synonyms
ValueSource
2-chloro-Acetic acidChEBI
2-chloro-Ethanoic acidChEBI
2-Chloroacetic acidChEBI
Acide chloracetiqueChEBI
Acide chloroacetiqueChEBI
Acide monochloracetiqueChEBI
alpha-chloro-Acetic acidChEBI
CAAChEBI
Chloracetic acidChEBI
Chloroethanoic acidChEBI
MonochloressigsaeureChEBI
Monochloroacetic acidChEBI
Monochloroethanoic acidChEBI
2-chloro-AcetateGenerator
ChloroacetateGenerator
2-chloro-EthanoateGenerator
2-ChloroacetateGenerator
a-chloro-AcetateGenerator
a-chloro-Acetic acidGenerator
alpha-chloro-AcetateGenerator
α-chloro-acetateGenerator
α-chloro-acetic acidGenerator
ChloracetateGenerator
ChloroethanoateGenerator
MonochloroacetateGenerator
MonochloroethanoateGenerator
AcetocaustinHMDB
AcidomonocloroaceticoHMDB
alpha-Chloroacetic acidHMDB
CH2ClCOOHHMDB
chloro-Acetic acidHMDB
ChloroaceticHMDB
Chloroacetic acid (80% or less)HMDB
Chloroacetic acid crystallineHMDB
Chloroacetic acid, acsHMDB
Chloroacetic acid, liquidHMDB
Chloroacetic acid, moltenHMDB
Chloroacetic acid, solidHMDB
Chloroacetic acid, solid (dot)HMDB
Chloroacetic-acidHMDB
MCAHMDB
MonochloorazijnzuurHMDB
Monochloracetic acidHMDB
Monochloracetic acidacide monochloracetiqueHMDB
Sjphlqdiktp@HMDB
Chloroacetic acid, calcium saltMeSH
Chloroacetic acid, sodium (2:1) saltMeSH
Chloroacetic acid, sodium (5:2) saltMeSH
Chloroacetic acid, ammonium (2:1) saltMeSH
Chloroacetic acid, aluminum saltMeSH
Chloroacetic acid, ammonium saltMeSH
Chloroacetic acid, potassium (2:1) saltMeSH
Chloroacetic acid, silver saltMeSH
Chloroacetic acid, sodium saltMeSH
SODIUM chloroacetATEMeSH
Chloroacetic acid, calcium (3:1) saltMeSH
Chloroacetic acid, potassium saltMeSH
Chemical FormulaC2H3ClO2
Average Molecular Weight94.497
Monoisotopic Molecular Weight93.982157047
IUPAC Name2-chloroacetic acid
Traditional Namechloroacetic acid
CAS Registry Number79-11-8
SMILES
OC(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyFOCAUTSVDIKZOP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility858 mg/mL at 25 °CNot Available
LogP0.22Not Available
Predicted Properties
PropertyValueSource
Water Solubility280 g/LALOGPS
logP0.18ALOGPS
logP0.31ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.4 m³·mol⁻¹ChemAxon
Polarizability7.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-d7ad64391c96deb3de35View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9200000000-940fedbd6b6f8c55c5a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-aaf6edb2b5574f74bdcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-38b0717f7c29f1ea92eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-938f17816bbc5dcba3e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-326c23d93ef6d226df1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-fcac67e5e20790848ebdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-27e8aa335107dedd6cd7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003394
KNApSAcK IDNot Available
Chemspider ID10772140
KEGG Compound IDC06755
BioCyc IDCHLOROACETIC-ACID
BiGG IDNot Available
Wikipedia LinkChloroacetic acid
METLIN IDNot Available
PubChem Compound300
PDB IDR3W
ChEBI ID27869
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Horisaki T, Yoshida E, Sumiya K, Takemura T, Yamane H, Nojiri H: Isolation and characterization of monochloroacetic acid-degrading bacteria. J Gen Appl Microbiol. 2011;57(5):277-84. [PubMed:22139456 ]
  2. Gomha SM, Khalil KD: A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules. 2012 Aug 3;17(8):9335-47. doi: 10.3390/molecules17089335. [PubMed:22864241 ]
  3. Baldessari A: Lipases as catalysts in synthesis of fine chemicals. Methods Mol Biol. 2012;861:445-56. doi: 10.1007/978-1-61779-600-5_25. [PubMed:22426733 ]
  4. Zhang YK, Li W, Wu KY, Chen GG, Liang ZQ: Purification and characterization of an intracellular alpha-glucosidase with high transglycosylation activity from A. niger M-1. Prep Biochem Biotechnol. 2011;41(2):201-17. doi: 10.1080/10826068.2011.547384. [PubMed:21442555 ]
  5. Ahuja M, Singh S, Kumar A: Evaluation of carboxymethyl gellan gum as a mucoadhesive polymer. Int J Biol Macromol. 2013 Feb;53:114-21. doi: 10.1016/j.ijbiomac.2012.10.033. Epub 2012 Nov 21. [PubMed:23178342 ]
  6. Sa CS, Boaventura RA, Pereira IB: Analysis of haloacetic acids in water and air (aerosols) from indoor swimming pools using HS-SPME/GC/ECD. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2012;47(2):176-83. doi: 10.1080/10934529.2012.640246. [PubMed:22242869 ]
  7. Naderi M, Eshghi P, Cohan N, Miri-Moghaddam E, Yaghmaee M, Karimi M: Successful delivery in patients with FXIII deficiency receiving prophylaxis: report of 17 cases in Iran. Haemophilia. 2012 Sep;18(5):773-6. doi: 10.1111/j.1365-2516.2012.02785.x. Epub 2012 Mar 28. [PubMed:22458944 ]
  8. Fomina EI: [A gas-chromatographic method of analysis of monochloroacetic acid and its sodium salt in the air, skin washings, protective clothing extracts and urine]. Gig Tr Prof Zabol. 1991;(12):39-41. [PubMed:1840108 ]
  9. Tang S, Wang XM, Yang HW, Xie YF: Haloacetic acid removal by sequential zero-valent iron reduction and biologically active carbon degradation. Chemosphere. 2013 Jan;90(4):1563-7. doi: 10.1016/j.chemosphere.2012.09.046. Epub 2012 Oct 15. [PubMed:23079162 ]
  10. Viozquez SF, Banon-Caballero A, Guillena G, Najera C, Gomez-Bengoa E: Enantioselective direct aldol reaction of alpha-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions. Org Biomol Chem. 2012 May 28;10(20):4029-35. doi: 10.1039/c2ob25224d. Epub 2012 Apr 18. [PubMed:22514086 ]
  11. Chen CH, Chen SJ, Su CC, Yen CC, Tseng TJ, Jinn TR, Tang FC, Chen KL, Su YC, Lee kI, Hung DZ, Huang CF: Chloroacetic acid induced neuronal cells death through oxidative stress-mediated p38-MAPK activation pathway regulated mitochondria-dependent apoptotic signals. Toxicology. 2013 Jan 7;303:72-82. doi: 10.1016/j.tox.2012.10.008. Epub 2012 Oct 26. [PubMed:23103613 ]
  12. Vaghani SS, Patel MM, Satish CS, Patel KM, Jivani NP: Synthesis and characterization of carboxymethyl chitosan hydrogel: application as pH-sensitive delivery for nateglinide. Curr Drug Deliv. 2012 Nov;9(6):628-36. [PubMed:22452405 ]
  13. Mushtaque M, Avecilla F, Azam A: Synthesis, characterization and structure optimization of a series of thiazolidinone derivatives as Entamoeba histolytica inhibitors. Eur J Med Chem. 2012 Sep;55:439-48. doi: 10.1016/j.ejmech.2012.06.052. Epub 2012 Jul 4. [PubMed:22840694 ]
  14. Li X, Ma J, Liu G, Fang J, Yue S, Guan Y, Chen L, Liu X: Efficient reductive dechlorination of monochloroacetic acid by sulfite/UV process. Environ Sci Technol. 2012 Jul 3;46(13):7342-9. doi: 10.1021/es3008535. Epub 2012 Jun 22. [PubMed:22681542 ]
  15. Singh RK, Khatri OP: A scanning electron microscope based new method for determining degree of substitution of sodium carboxymethyl cellulose. J Microsc. 2012 Apr;246(1):43-52. doi: 10.1111/j.1365-2818.2011.03583.x. Epub 2011 Dec 12. [PubMed:22150298 ]
  16. Meng L, Wu S, Ma F, Jia A, Hu J: Trace determination of nine haloacetic acids in drinking water by liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr A. 2010 Jul 16;1217(29):4873-6. doi: 10.1016/j.chroma.2010.04.074. Epub 2010 May 24. [PubMed:20538280 ]
  17. Kurita Y, Isogai A: N-Alkylations of chitosan promoted with sodium hydrogen carbonate under aqueous conditions. Int J Biol Macromol. 2012 Apr 1;50(3):741-6. doi: 10.1016/j.ijbiomac.2011.12.004. Epub 2011 Dec 17. [PubMed:22197793 ]
  18. Iglesias E, Brandariz I: A further study of acetylacetone nitrosation. Org Biomol Chem. 2013 Feb 14;11(6):1059-64. doi: 10.1039/c2ob26073e. Epub 2013 Jan 3. [PubMed:23288218 ]
  19. Naik TR, Naik HS, Prabhakara MC: One-pot solvent free synthesis and DNA binding studies of thieno[2,3-b]-1,8-naphthyridines. Prep Biochem Biotechnol. 2008;38(1):115-28. [PubMed:18080916 ]
  20. Zhang B, Gong H, Lu S, Ni B, Liu M, Gao C, Huang Y, Han F: Synthesis and characterization of carboxymethyl potato starch and its application in reactive dye printing. Int J Biol Macromol. 2012 Nov;51(4):668-74. doi: 10.1016/j.ijbiomac.2012.07.003. Epub 2012 Jul 8. [PubMed:22782070 ]
  21. Chapman T, Mahadevan D, Mahajan A, Perez-Temprano A, McDiarmid J: Iatrogenic full-thickness chemical burns from monochloracetic acid. J Burn Care Res. 2006 Jul-Aug;27(4):545-7. [PubMed:16819363 ]
  22. Bruzzoniti MC, De Carlo RM, Sarzanini C, Caldarola D, Onida B: Novel insights in Al-MCM-41 precursor as adsorbent for regulated haloacetic acids and nitrate from water. Environ Sci Pollut Res Int. 2012 Nov;19(9):4176-83. doi: 10.1007/s11356-012-0900-6. Epub 2012 Apr 17. [PubMed:22529001 ]
  23. Xu Q, Xu B, Qin C, Xia SJ, Gao NY, Tian FX, Li DP: [Chlorination byproducts formation potentials of typical nitrogenous organic compounds in water]. Huan Jing Ke Xue. 2011 Jul;32(7):1967-73. [PubMed:21922816 ]
  24. Wang CX, Song QP: Removal of Cu(II) ions from aqueous solutions using N-carboxymethyl chitosan. Water Sci Technol. 2012;66(9):2027-32. doi: 10.2166/wst.2012.419. [PubMed:22925879 ]
  25. Singh AV, Singh A, Nath LK: Microwave assisted synthesis and evaluation of modified pea starch as tablet superdisintegrant. Curr Drug Deliv. 2011 Mar;8(2):203-7. [PubMed:21235480 ]
  26. Bidgoli H, Zamani A, Taherzadeh MJ: Effect of carboxymethylation conditions on the water-binding capacity of chitosan-based superabsorbents. Carbohydr Res. 2010 Dec 10;345(18):2683-9. doi: 10.1016/j.carres.2010.09.024. Epub 2010 Sep 25. [PubMed:20971451 ]
  27. Ahuja M, Kumar A, Singh K: Synthesis, characterization and in vitro release behavior of carboxymethyl xanthan. Int J Biol Macromol. 2012 Dec;51(5):1086-90. doi: 10.1016/j.ijbiomac.2012.08.023. Epub 2012 Aug 27. [PubMed:22947448 ]
  28. Gong P, Peng S, He J, Deng M, Jiang B, Wang K: One-step synthesis of glucose-branched galactomannan. Carbohydr Res. 2011 Sep 27;346(13):1973-7. doi: 10.1016/j.carres.2011.06.012. Epub 2011 Jun 16. [PubMed:21742317 ]
  29. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails