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 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:64777

ChemSpider |

* 15666

EC Number |

* 218-433-0

PubChem CID

* 16526

UNII |

* 48431VN59G Y

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

Tracking categories (test):

* SizeSet

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". 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. https://openprairie.sdstate.edu/chem_pubs/42.

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*[CID]: Compound ID