375004
2,4-Thiazolidinedione
technical grade, 90%
Synonym(s):
2,4(3H,5H)-Thiazoledione, 2,4-Dioxo-1,3-thiazolidine, 2,4-Dioxothiazolidine, 2-Hydroxy-4,5-dihydro-1,3-thiazol-4-one, Thiazole-2,4-dione, Thiazolidin-2,4-dione, Thiazolidinedione (6CI)
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About This Item
Empirical Formula (Hill Notation):
C3H3NO2S
CAS Number:
Molecular Weight:
117.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-941-2
Beilstein/REAXYS Number:
110700
MDL number:
Assay:
90%
InChI key
ZOBPZXTWZATXDG-UHFFFAOYSA-N
InChI
1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
SMILES string
O=C1CSC(=O)N1
grade
technical grade
assay
90%
mp
125-127 °C (lit.)
Quality Level
Related Categories
General description
2,4-Thiazolidinedione is a well-known peroxisome proliferator-activated receptors (PPAR) activator. Its effect on aging process using kidneys from Fischer 344 rats has been reported. A library of conjugates of 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C catalyst. Knoevenagel condensation of various aromatic aldehydes with 2,4-thiazolidinedione in polyethylene glycol-300 has been reported.
Application
2,4-Thiazolidinedione may be used in the synthesis of sixteen 5-arylidene-2,4-thiazolidinediones, via ultrasound-promoted aldol condensation reaction. It may be used as starting material for the synthesis of drugs with antihyperglycemic activity.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Tien-Jyun Chang et al.
Pharmacogenetics and genomics, 21(12), 829-836 (2011-09-22)
This study aimed to analyze the association of thiazolidinedione (TZD)-related edema with genetic and clinical variables and develop a simple points system to predict the risk of developing TZD-related edema. Fifty-eight (21.6%) of 268 individuals who received TZD for type
Suzanne V Arnold et al.
Circulation. Heart failure, 12(6), e005855-e005855 (2019-05-28)
Background Thiazolidinediones (rosiglitazone, pioglitazone) are oral insulin-sensitizing medications used in type 2 diabetes mellitus that reduce glucose with minimal risk of hypoglycemia and potential benefits on atherosclerosis. However, thiazolidinediones can cause fluid retention thereby increasing the risk of heart failure-a
A Koch et al.
British journal of pharmacology, 166(3), 1018-1032 (2012-01-10)
PPARγ agonists [thiazolidinediones (TZDs)] are known to exert anti-fibrotic effects in the kidney. In addition, we previously demonstrated that sphingosine kinase 1 (SK-1) and intracellular sphingosine-1-phosphate (S1P), by reducing the expression of connective tissue growth factor (CTGF), have a protective
A Zask et al.
Journal of medicinal chemistry, 33(5), 1418-1423 (1990-05-01)
A series of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2,4-thiazolidinedione with appropriate sulfonyl
Oscar Lamas Longarela et al.
PloS one, 8(3), e58340-e58340 (2013-03-19)
The hepatitis delta virus (HDV) is a small, defective RNA virus that requires the presence of the hepatitis B virus (HBV) for its life cycle. Worldwide more than 15 million people are co-infected with HBV and HDV. Although much effort
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