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Sigma-Aldrich

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
MDL number:
MFCD00068005
UNSPSC Code:
12352100
PubChem Substance ID:
24870454
NACRES:
NA.22

Assay

97%

mp

176 °C (lit.)

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. 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.

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).

Pictograms

Exclamation mark
GHS07

Signal Word

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
Inhibition of dopamine beta-hydroxylase by thiazoline-2-carboxylate, a suspected physiological product of D-amino acid oxidase.
N Naber et al.
Biochemical and biophysical research communications, 107(1), 374-380 (1982-07-16)
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
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