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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

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 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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