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Merck
CN

467995

Thiazolidine-2-carboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2S
CAS Number:
65126-70-7
Molecular Weight:
133.17
NACRES:
NA.22
PubChem Substance ID:
24870454
UNSPSC Code:
12352100
MDL number:
MFCD00068005

Key Documents

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Product Name

Thiazolidine-2-carboxylic acid, 97%

InChI

1S/C4H7NO2S/c6-4(7)3-5-1-2-8-3/h3,5H,1-2H2,(H,6,7)

SMILES string

OC(=O)C1NCCS1

InChI key

ULSZVNJBVJWEJE-UHFFFAOYSA-N

assay

97%

mp

176 °C (lit.)

functional group

carboxylic acid
thioether

Quality Level

100

Related Categories

Application

Thiazolidine-2-carboxylic acid may be used in the synthesis of azabicycloadducts and 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates).

General description

Thiazolidine-2-carboxylic acid (β-thiaproline) is a proline analog. It is an important building block of β-lactam antibiotics. Its X-ray photoelectron spectra has been investigated. It has been reported as a physiological substrate of hog kidney D-amino acid oxidase. Thiazolidine-2-carboxylic acid can be synthesized from cysteamine and glyoxylate.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8414
MKCZ1825
MKCW4464
MKCS0311
MKCP5124

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C L Burns et al.
Biochemical and biophysical research communications, 125(3), 1039-1045 (1984-12-28)
Adducts of glyoxylate with L-cysteine or L-cysteinylglycine were found to be excellent substrates at low concentrations for beef kidney D-aspartate oxidase. Evidence is presented that cis-thiazolidine-2,4-dicarboxylate and its glycine amide are the actual substrates, and that both are converted in
V Busiello et al.
Biochimica et biophysica acta, 564(2), 311-321 (1979-09-27)
Thiazolidine-2-carboxylic acid, or beta-thiaproline, is a proline analog in which the beta methylene group of proline is substituted by a sulfur atom. It has been deomonstrated that beta-thiaproline is activated and transferred to tRNAPro by Escherichia coli and rat liver
L Włodek et al.
Biochemical pharmacology, 46(1), 190-193 (1993-07-06)
2-Substituted thiazolidine-4(R)-carboxylic acids (TD) were found to increase the concentration of non-protein sulphydryls (NPSH) and the activity of rhodanese (thiosulphate sulphurtransferase, EC 2.8.1.1) and 3-mercaptopyruvate sulphurtransferase (EC 2.8.1.2) in mouse liver. These properties suggest TDs are potentially hepatoprotective compounds. However
Synthesis and chromatographic properties of selenazolidine-2-carboxylic acid (beta-selenaproline).
C De Marco et al.
The Italian journal of biochemistry, 28(2), 104-110 (1979-03-01)
Fang Xie et al.
Journal of fluorescence, 28(1), 89-96 (2017-09-11)
Copper complexes with strong anticancer activity are promising new drugs for treatment of patients with metastatic cancer. Copper 8-hydroxyquinoline-2-carboxaldehyde-thiosemicarbazide (CuHQTS) and copper 8-hydroxyquinoline-2-carboxaldehyde-4,4-dimethyl-3-thiosemicarbazide (CuHQDMTS) were found to have strong anticancer activity against cisplatin-resistant neuroblastoma cells and prostate cancer cells. This
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Articles

Proline Derivatives and Analogs

Proline analogues are promising candidates for tuning the biological, pharmaceutical, or physicochemical properties of naturally occuring, as well as de novo designed, linear, and, cyclic peptides.

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