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Merck

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:
2295-31-0
Molecular Weight:
117.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863353
EC Number:
218-941-2
Beilstein/REAXYS Number:
110700
MDL number:
MFCD00005478
Assay:
90%

Key Documents

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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

100

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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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000443728
0000443728
BCCM2006
BCCK1446
0000173815

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K M Schoenberg et al.
Journal of dairy science, 94(11), 5523-5532 (2011-10-29)
Administration of peroxisome proliferator-activated receptor gamma (PPARγ) ligands, thiazolidinediones (TZD), to prepartum dairy cattle has been shown to improve dry matter intake and decrease circulating nonesterified fatty acids (NEFA) around the time of calving. The objective of this work was
Shana Jaaf et al.
Veterinary sciences, 6(2) (2019-05-22)
Background: In a prior experiment, treatment of goats with the putative PPARγ agonist 2,4-thiazolidinedione (2,4-TZD) did not affect milk fat or expression of milk-fat related genes. The lack of response was possibly due to deficiency of vitamin A and/or a
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
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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