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3-Chloropropanoic acid

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(Redirected from 3-chloropropanoic acid) Chemical compound

Pharmaceutical compound
3-Chloropropanoic acid
Identifiers
IUPAC name
  • 3-chloropropionic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.003.214 Edit this at Wikidata
Chemical and physical data
FormulaC3H5ClO2
Molar mass108.52 g·mol
3D model (JSmol)
Melting point42 °C (108 °F)
Boiling point204 °C (399 °F) (decomp.)
SMILES
  • C(CCl)C(=O)O
InChI
  • InChI=1S/C3H5ClO2/c4-2-1-3(5)6/h1-2H2,(H,5,6)
  • Key:QEYMMOKECZBKAC-UHFFFAOYSA-N
  (verify)

3-Chloropropanoic acid (also known as 3-chloropropionic acid or UMB66) is the organic compound with the formula ClCH2CH2CO2H. A white or colorless solid, it is used as a drug and a synthetic intermediate. The compound is produced by the hydrochlorination of acrylic acid. In aqueous solution, it has a pKa value of 4.08.

This compound is used in scientific research. It is structurally related to GHB and binds to the GHB receptor, but has no affinity for GABA receptors. It is also an active ingredient in some herbicide blends. Overdose may cause unconsciousness and/or convulsions. It has been demonstrated that the substance can be broken down by both bacteria and fungi as a means of bioremediation.

References

  1. Samel U, Kohler W, Gamer AO, Keuser U (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
  2. Dixon SL, Jurs PC (December 1993). "Estimation of p K a for organic oxyacids using calculated atomic charges". Journal of Computational Chemistry. 14 (12): 1460–1467. doi:10.1002/jcc.540141208. ISSN 0192-8651.
  3. Macias AT, Hernandez RJ, Mehta AK, MacKerell AD, Ticku MK, Coop A (April 2004). "3-chloropropanoic acid (UMB66): a ligand for the gamma-hydroxybutyric acid receptor lacking a 4-hydroxyl group". Bioorganic & Medicinal Chemistry. 12 (7): 1643–1647. doi:10.1016/j.bmc.2004.01.025. PMID 15028257.
  4. ^ Ng HJ, Roswanira A, Ronald AC, Fahrul H (2005). "Degradation Of Herbicide (3-Chloropropionic Acid) By Bacterial Dehalogenases" (PDF). Proc. KUSTEM 4th Annual Seminar 2005: 586–590. Archived from the original (PDF) on 2016-03-05.
  5. "Chemical Data Sheet for 3-CHLOROPROPIONIC ACID". NOAA.
  6. Edbeib M (2020-04-15). "3-Chloropropionic Acid (3cp) Degradation and Production of Propionic Acid by Newly Isolated Fungus Trichoderma Sp. Mf1". International Journal of Life Sciences and Biotechnology. 3 (1): 41–50. doi:10.38001/ijlsb.677005. ISSN 2651-4621.
GHB receptor modulators
Receptor
(ligands)
GHBRTooltip GHB receptor
GABABTooltip γ-Aminobutyric acid B receptor
Transporter
(blockers)
MCTsTooltip Monocarboxylate transporters
SMCTsTooltip Sodium-coupled monocarboxylate transporters
VIATTTooltip Vesicular inhibitory amino acid transporter
Enzyme
(inhibitors)
SSRTooltip Succinic semialdehyde reductase
GHBDHTooltip 4-Hydroxybutyrate dehydrogenase
HOTTooltip Hydroxyacid-oxoacid transhydrogenase
ADHTooltip Alcohol dehydrogenase
ALDHTooltip Aldehyde dehydrogenase
See also
Receptor/signaling modulators
GABA receptor modulators
Glutamate receptor modulators
Glycine receptor modulators
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