2-Aminothiazoline-4-carboxylic acid

2-Aminothiazoline-4-carboxylic acid
Names
Preferred IUPAC name
2-Amino-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Other names
ACTA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.016.758 Edit this at Wikidata
EC Number
  • 218-433-0
UNII
  • InChI=1S/C4H6N2O2S/c5-4-6-2(1-9-4)3(7)8/h2H,1H2,(H2,5,6)(H,7,8)
    Key: VHPXSBIFWDAFMB-UHFFFAOYSA-N
  • C1C(N=C(S1)N)C(=O)O
Properties
C4H6N2O2S
Molar mass 146.16 g·mol−1
Appearance White solid
Melting point 212 °C (414 °F; 485 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Aminothiazoline-4-carboxylic acid (ACTA) is the organosulfur compound and a heterocycle with the formula HO2CCHCH2SCNH2N. This derivative of thiazoline is an intermediate in the industrial synthesis of L-cysteine, an amino acid. ACTA exists in equilibrium with its tautomer 2-iminothiazolidine-4-carboxylic acid.

It is produced by the reaction of methyl chloroacrylate with thiourea.[1] It is also a biomarker for cyanide poisoning, as it results from the condensation of cysteine and cyanide.[2]

References

  1. ^ Karlheinz Drauz; Ian Grayson; Axel Kleemann; Hans-Peter Krimmer; Wolfgang Leuchtenberger, Christoph Weckbecker (2006). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_057.pub2. ISBN 978-3527306732.
  2. ^ Logue, Brian A.; Kirschten, Nicholas P.; Petrikovics, Ilona; Moser, Matthew A.; Rockwood, Gary A.; Baskin, Steven I. (2005). "Determination of the cyanide metabolite 2-aminothiazoline-4-carboxylic acid in urine and plasma by gas chromatography-mass spectrometry". Journal of Chromatography B. 819 (2): 237–244. doi:10.1016/j.jchromb.2005.01.045. PMID 15833287.