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
CAS Number	2150-55-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:64777;
ChemSpider	15666;
ECHA InfoCard	100.016.758
EC Number	218-433-0;
PubChem CID	16526;
UNII	48431VN59G ;
CompTox Dashboard (EPA)	DTXSID9024510 ;
	InChI 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;
	SMILES C1C(N=C(S1)N)C(=O)O;
Properties
Chemical formula	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). Infobox references

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

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.
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.

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[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.

[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.