Oxothiazolidinecarboxylic acid

Names

[ CAS No. ]:
19771-63-2

[ Name ]:
Oxothiazolidinecarboxylic acid

[Synonym ]:
L-2-Oxothiazolidine-4-carboxylic Acid
2-oxothiazolidine-4(R)-carboxylic acid
4-Thiazolidinecarboxylic acid, 2-oxo-, (4R)-
4-Thiazolidinecarboxylic acid,2-oxo-,(R)-[]
OTCA
L-2-Oxothiazolidine-4-carboxylate
(4R)-2-Oxothiazolidine-4-carboxylic acid
(R)-(−)-2-Oxothiazolidine-4-carboxylic acid L-(−)-2-Oxothiazolidine-4-carboxylic acid
L-2-Oxo-4-thiazolidinecarboxylic acid
(R)-2-oxothiazolidine-4-carboxylic acid
L-(−)-2-Oxothiazolidine-4-carboxylic acid
(4R)-2-Oxo-1,3-thiazolidine-4-carboxylic acid
(−)-2-Oxo-4-thiazolidinecarboxylic acid
MFCD00066092
Procysteine
Oxothiazolidine carboxylate,L
(4R)-2-oxo-4-thiazolidine-carboxylic acid
4-Thiazolecarboxylic acid, 4,5-dihydro-2-hydroxy-, (4R)-
(4R)-2-Hydroxy-4,5-dihydro-1,3-thiazole-4-carboxylic acid
L-2-Thiazolidinone-4-carboxylic Acid
2-Oxothiazolidine-4-carboxylate,L
(R)-(−)-2-Oxothiazolidine-4-carboxylic acid

Biological Activity

[Description]:

Oxothiazolidinecarboxylic acid, an antioxidant, is a prodrug of cysteine that is inert until metabolized to cysteine intracellulary, thus stimulating glutathione synthesis[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vivo]

Oxothiazolidinecarboxylic acid treatment attenuates plantaris atrophy, restored glutathione levels, and increased catalase, Cu/Zn-SOD1, and Mn-SOD2 mRNA expression, but did not reduce other markers of oxidant stress or levels of these catabolic factors[1]. Animal Model: Male Sprague-Dawley rats (200-250 g, n= 6-7 rats/group)[1]. Dosage: 0.35% (w/v). Administration: Added to their diets at a concentration of 0.35% (w/v) for the final 12 wk. Result: Increased fiber CSAs compared to the non-supplemented, alcohol-fed group.

[References]

[1]. Jeffrey S Otis, et al. Procysteine Stimulates Expression of Key Anabolic Factors and Reduces Plantaris Atrophy in Alcohol-Fed Rats. Alcohol Clin Exp Res. 2009 Aug;33(8):1450-9.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Melting Point ]:
174 °C (dec.)(lit.)

[ Molecular Formula ]:
C₄H₅NO₃S

[ Molecular Weight ]:
147.152

[ Exact Mass ]:
146.999008

[ PSA ]:
91.70000

[ LogP ]:
-1.11

[ Index of Refraction ]:
1.595

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XJ5426650

CHEMICAL NAME :: 4-Thiazolidinecarboxylic acid, 2-oxo-, (R)-

CAS REGISTRY NUMBER :: 19771-63-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C4-H5-N-O3-S

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACTDZ Journal of the American College of Toxicology. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1-12, 1982-1993. Discontinued. Volume(issue)/page/year: 12,109,1993

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ATDAEI Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 1,164,1992

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ATDAEI Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 1,164,1992

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XJ5426650

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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