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467995

Sigma-Aldrich

Thiazolidine-2-carboxylic acid

97%

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About This Item

Fórmula empírica (notación de Hill):
C4H7NO2S
Número de CAS:
65126-70-7
Peso molecular:
133.17
MDL number:
MFCD00068005
UNSPSC Code:
12352100
PubChem Substance ID:
24870454
NACRES:
NA.22
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Quality Level

100

assay

97%

mp

176 °C (lit.)

functional group

carboxylic acid
thioether

SMILES string

OC(=O)C1NCCS1

InChI

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

InChI key

ULSZVNJBVJWEJE-UHFFFAOYSA-N

General description

Thiazolidine-2-carboxylic acid (β-thiaproline) is a proline analog.[1] It is an important building block of β-lactam antibiotics. Its X-ray photoelectron spectra has been investigated.[2] 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.[3]

Application

Thiazolidine-2-carboxylic acid may be used in the synthesis of azabicycloadducts[4] and 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates).[5]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCW4464
MKCS0311
MKCP5124
MKCL8352
MKCK4954

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Sonali Verma et al.
Organic and medicinal chemistry letters, 1(1), 6-6 (2012-03-01)
A facile synthesis of azabicycloadducts is described by 1,3-dipolar cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid in the presence of various electron rich and electron deficient dipolarophiles. Theoritical calculations have been performed to study the regioselectivity of products. The geometrical
P F Fitzpatrick et al.
The Journal of biological chemistry, 257(3), 1166-1171 (1982-02-10)
A mixture of cysteamine and glyoxylate, proposed by Hamilton et al. to form the physiological substrate of hog kidney D-amino acid oxidase (Hamilton, G. A., Buckthal, D. J., Mortensen, R. M., and Zerby, K. W. (1979) Proc. Natl. Acad. Sci.
I Lalezari et al.
Journal of medicinal chemistry, 31(7), 1427-1429 (1988-07-01)
A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia
W M Frederiks et al.
The Histochemical journal, 25(8), 578-582 (1993-08-01)
D-Amino acid oxidase activity was demonstrated in peroxisomes of rat liver using unfixed cryostat sections and a histochemical technique using cerium ions as capture reagent for hydrogen peroxide and diaminobenzidine, cobalt ions and exogenous hydrogen peroxide to visualize the final
C Foppoli et al.
The Italian journal of biochemistry, 30(5), 355-366 (1981-09-01)
Beta-DL-Thiaproline (thiazolidine 2-carboxylic acid) is a good substrate for hog kidney D-aminoacid oxidase. Unlike other known substrates, beta-thiaproline is better oxidized at neutral than at alkaline pH. At neutral pH beta-thiaproline is a better substrate than D-proline. Beta-DL-thiaproline is fully
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