Thiazolidinedione

HCID 5437CAS 2295-31-0
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1CSC(=O)N1
InChIKey
ZOBPZXTWZATXDG-UHFFFAOYSA-N
Molecular formula
C3H3NO2S
Average molar mass
117.13 g/mol
Monoisotopic mass
116.98844934

Overview

1,3-thiazolidine-2,4-dione is a thiazolidenedione carrying oxo substituents at positions 2 and 4. It derives from a hydride of a 1,3-thiazolidine.

Names & identifiers

Preferred name
Thiazolidinedione
IUPAC
1,3-thiazolidine-2,4-dione
English name
2,4-Thiazolidinedione
Molecular formula
C3H3NO2S
Molecular weight
117.13

Names & synonyms

2,4-THIAZOLIDINEDIONE2295-31-0Thiazolidinedione2,4-Dioxothiazolidine2,4(3H,5H)-ThiazoledioneNSC-6745AA68LXK93CDTXSID5040623RefChem:932950DTXCID3020623Thiazolidinedione Antidiabetic Agent218-941-2
Show more names
TZD2,4-ThiazolidindioneU 25560idinedioneusafek-54962,4-ThiazoLAURORA 23272
1,3-Thiazolidine-2,4-dionethiazolidine-2,4-dioneUSAF EK-5496MFCD00005478ThiazolidindioneC3H3NO2SNSC 67452,4thiazolidinedione

Database identifiers

CAS
2295-31-0
PubChem CID
5437
DTXSID
DTXSID5040623
ChEMBL
CHEMBL85398
ChEBI
CHEBI:50992
UNII
AA68LXK93C
EC Number
218-941-2
Nikkaji
J48.702C

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
71.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
7

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point
125 · 125-127 °C (lit.)
Boiling point
178 · 178-179 °C (19 mmHg)
Density
1.408 · 1.408 (estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.513 · 1.5130 (estimate)
Flash point
178 · 178-179°C/19mm

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 15.4% (2 of 13) of reports.

Warning

H302 (53.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 13 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Cease Manufacture Update: 01-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19571
Hazard Classes and CategoriesAcute Tox. 4 (53.8%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
XJ5775000
hs_code
29341000
risk_code
36/37/38

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.

Uses & manufacturing

General Manufacturing Information2,4-Thiazolidinedione: ACTIVE
Applications · 3 items

UsesInhibitor of enzyme

Uses2,4-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 Description2,4-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.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京京宇复瑞科技集团有限责任公司010-83694934 13671295325
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: A thiazolidenedione carrying oxo substituents at positions 2 and 4.

Related reactions

702 records
New reaction record

Linked notes

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