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375004

Sigma-Aldrich

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
Beilstein/REAXYS Number:
110700
EC Number:
218-941-2
MDL number:
MFCD00005478
UNSPSC Code:
12352100
PubChem Substance ID:
24863353
NACRES:
NA.22

grade

technical grade

Quality Level

100

assay

90%

mp

125-127 °C (lit.)

SMILES string

O=C1CSC(=O)N1

InChI

1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)

InChI key

ZOBPZXTWZATXDG-UHFFFAOYSA-N

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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_germany

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
BCCM2006
BCCK1446
0000173815
BCCD4932
0000022092

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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
Ming-Chang Chiang et al.
Neurobiology of disease, 45(1), 322-328 (2011-09-13)
Huntington's disease (HD) is an autosomal dominant neurodegenerative disease caused by a CAG trinucleotide expansion in the Huntingtin (Htt) gene. The resultant mutant Htt protein (mHtt) forms aggregates in the brain (e.g., cortex and striatum), and causes devastating neuronal degeneration.
Bruna B Drawanz et al.
Ultrasonics sonochemistry, 21(5), 1615-1617 (2014-05-17)
The efficient synthesis of sixteen 5-arylidene-2,4-thiazolidinediones by aldol condensation reaction of 2,4-thiazolidinedione, mono- and di-substituted arenealdehydes and KOH using ultrasound irradiation is reported. The desired compounds were obtained in a few min (10-30 min) with moderate to good yields (25-81%).
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