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O6254

Sigma-Aldrich

(R)-(−)-2-Oxothiazolidine-4-carboxylic acid

≥98% (titration), suitable for plant cell culture

Synonym(s):

L-(−)-2-Oxothiazolidine-4-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C4H5NO3S
CAS Number:
19771-63-2
Molecular Weight:
147.15
Beilstein:
4179169
MDL number:
MFCD00066092
UNSPSC Code:
12352106
PubChem Substance ID:
24898032
NACRES:
NA.26

product name

(R)-(−)-2-Oxothiazolidine-4-carboxylic acid, ≥97% (TLC), ≥98% (titration)

Quality Level

200

Assay

≥97% (TLC)
≥98% (titration)

form

(powder to crystals)

technique(s)

cell culture | plant: suitable

color

white to off-white

SMILES string

OC(=O)[C@@H]1CSC(=O)N1

InChI

1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1

InChI key

BMLMGCPTLHPWPY-REOHCLBHSA-N

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Application


  • Artificial elevation of glutathione contents in salicylic acid-deficient tobacco (Nicotiana tabacum cv. Xanthi NahG) reduces susceptibility to the powdery mildew pathogen Euoidium longipes.: This study explores the impact of enhanced glutathione levels on resistance to powdery mildew in tobacco plants deficient in salicylic acid, indicating a potential application of R-(−)-2-Oxothiazolidine-4-carboxylic acid in managing plant diseases (Künstler et al., 2020).

Biochem/physiol Actions

2-Oxothiazolidine-4-carboxylic acid augments glutathione and cysteine production.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Leonardo F Ferreira et al.
Journal of applied physiology (Bethesda, Md. : 1985), 107(1), 211-216 (2009-05-02)
Fatiguing exercise promotes oxidation of intracellular thiols, notably glutathione. Interventions that oppose or reverse thiol oxidation can inhibit fatigue. The reduced cysteine donor l-2-oxothiazolidine-4-carboxylate (OTC) supports glutathione synthesis and is approved for use in humans but has not been evaluated
Meshal Al Moutaery et al.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, 64(3), 233-237 (2010-09-11)
Earlier studies have suggested an important role of glutathione (GSH) in cytoprotection against free radicals induced oxidative damage. This study reports gastroprotective effects of a cysteine precursor, L-2-oxothiazolidine-4-carboxylate (OTC), in experimental models of gastric secretion and ulceration. Acid secretion studies
Nghi Phung et al.
International journal of molecular medicine, 24(2), 171-180 (2009-07-07)
The mechanistic significance of oxidative stress to fibrogenesis in the methionine and choline-deficient (MCD) diet-induced model of steatohepatitis was evaluated by antioxidant intervention, using either vitamin E or L-2-oxothiazolidine-4-carboxylate (OTC), a cysteine precursor that promotes glutathione synthesis. Significant depletion of
Erik R Kline et al.
American journal of physiology. Heart and circulatory physiology, 294(6), H2792-H2804 (2008-05-06)
Human immunodeficiency virus (HIV)-infected patients have a higher incidence of oxidative stress, endothelial dysfunction, and cardiovascular disease than uninfected individuals. Recent reports have demonstrated that viral proteins upregulate reactive oxygen species, which may contribute to elevated cardiovascular risk in HIV-1
F-M Huang et al.
International endodontic journal, 43(12), 1091-1097 (2010-07-22)
To evaluate ex vivo the mechanisms of cytotoxicity of dentine bonding agents in human pulp cells in vitro. Human pulp cells were obtained from impacted third molars with informed consent and then cultured using an explant technique. Set specimens from
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