2-Thioxothiazolidine-4-carboxylic Acid - CAS 20933-67-9
Catalog number: 20933-67-9
Category: Main Product
Molecular Formula:
Molecular Weight:
Off-White Solid
TTCA; 2-Thioxo-4-thiazolidinecarboxylic Acid; 2-Thioxothiazolidine-4-carboxylic Acid; Thiazolidine-2-thione-4-carboxylic Acid; 2-THIOTHIAZOLIDINE-4-CARBOXYLICACID; TTCA (Thiram Metabolite)
A metabolite of Carbon Disulfide.
Boiling Point:
359.4ºC at 760 mmHg
Canonical SMILES:
1.Identification of a new urinary metabolite of carbon disulfide using an improved method for the determination of 2-thioxothiazolidine-4-carboxylic acid.
Amarnath V1, Amarnath K, Graham DG, Qi Q, Valentine H, Zhang J, Valentine WM. Chem Res Toxicol. 2001 Sep;14(9):1277-83.
A new method is reported for the analysis of 2-thioxothiazolidine-4-carboxylic acid (TTCA) in urine that is amenable to automation and provides greatly simplified chromatograms. The method comprises the addition of tetrahydro-2-thioxo-2H-1,3-thiazine-4-carboxylic acid, which is chemically similar to TTCA, as internal standard, purification on an Oasis HLB solid-phase extraction column, and analysis by HPLC with UV detection. The limit of detection for TTCA was 40 pmol/mL of urine, recovery was 79.3 +/- 1.0%, and detection was linear over at least 3 orders of magnitude. In addition, during the analysis of urine samples from workers exposed to CS(2), a novel urinary metabolite of CS(2) was recognized. The new metabolite demonstrated a dose response, was present at approximately 30% the level of TTCA, and was charaterized to be 2-thioxothiazolidin-4-ylcarbonylglycine (TTCG). Administration of TTCG to rats resulted in excretion of TTCA suggesting that TTCG is a likely precursor of TTCA.
2.Liquid chromatographic determination of 2-thioxothiazolidine-4-carboxylic acid isolated from urine by affinity chromatography on organomercurial agarose gel.
Thienpont LM1, Depourcq GC, Nelis HJ, De Leenheer AP. Anal Chem. 1990 Dec 15;62(24):2673-5.
Urinary 2-thioxothiazolidine-4-carboxylic acid is a useful indicator to assess the degree of occupational exposure to carbon disulfide. A new procedure is described for the isolation of this compound from urine prior to reversed-phase high-performance liquid chromatography. It is based on liquid-liquid extraction with methyl tert-butyl ether, followed by affinity chromatography on organomercurial agarose gel. 5-Carboxythiouracil is used as internal standard. The superior selectivity of affinity chromatography for the isolation of 2-thioxothiazolidine-4-carboxylic acid from urine permits an isocratic high-performance liquid chromatographic analysis. The total recovery of 2.5 mg of 2-thioxothiazolidine-4-carboxylic acid/g of creatinine in spiked urine by liquid-liquid extraction combined with affinity chromatography was 48.0% (SD 2.0%, n = 8). Within-run and within-day relative standard deviations averaged 4.0% (means = 2.48 mg/g of urinary creatinine, n = 9) and 6.
3.(4R)-(-)-2-thioxothiazolidine-4-carboxylic acid (raphanusamic acid).
Dobson AJ1, Gerkin RE. Acta Crystallogr C. 1998 Nov 15;54 ( Pt 11):1634-7.
The title acid, C4H5NO2S2, crystallized in the noncentrosymmetric space group P2(1)2(1)2(1) with one molecule as the asymmetric unit. Two hydrogen bonds occur, namely, N--H...O, with a donor-acceptor distance of 2.850 (2) A, and O-H...S (resonance induced), with a donor-acceptor distance of 3.318 (2) A; both H atoms involved are ordered. These two types of bonds link a given molecule to four neighbors, the molecules linked being of space-group symmetry types 1 and 3, or 2 and 4. These two subsets of molecules alternate in layers along c. Three significant C-H...O interactions occur, one of which crosslinks the subsets just described to produce a three-dimensional network of linked molecules. The absolute structure is determined.
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CAS 20933-67-9 2-Thioxothiazolidine-4-carboxylic Acid

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