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

grade

technical grade

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Sabrina Heng et al.
Bioorganic & medicinal chemistry, 19(24), 7453-7463 (2011-11-15)
We present a new class of inhibitors of pancreatic cholesterol esterase (CEase) based on 'priviledged' 5-benzylidenerhodanine and 5-benzylidene-2,4-thiazolidinedione structural scaffolds. The lead structures (5-benzylidenerhodanine 4a and 5-benzylidene-2,4-thiazolidinedione 4b) were identified in an in-house screening and these inhibited CEase with some
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%).
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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