Thiazolidinedione
Basic information
- CAS
2295-31-0- Standard SMILES
O=C1CSC(=O)N1- InChIKey
ZOBPZXTWZATXDG-UHFFFAOYSA-N- Molecular formula
- C3H3NO2S
- Average molar mass
- 117.13 g/mol
- Monoisotopic mass
- 116.98844951
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-6745AA68LXK93CDTXSID5040623Thiazolidinedione Antidiabetic AgentRefChem:932950DTXCID3020623218-941-2
Show more names
TZD2,4-ThiazolidindioneU 25560idinedioneusafek-54962,4-ThiazoLAURORA 23272
1,3-Thiazolidine-2,4-dionethiazolidine-2,4-dioneThiazolidindioneUSAF EK-5496MFCD00005478Thiazolidinedione-2,4thiazolidin-2,4-dioneNSC 6745
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
- Formal charge
- 0
- Complexity
- 122
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
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 6.5 · 6.50±0.10(Predicted)
- color
- Slightly yellow
- Water Solubility
- Soluble in water (30 mg/ml at 3°C), methanol, DMSO, ethanol, and ethyl ether.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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 InformationREACH registered substance: Thiazolidine-2,4-dione (EC: 218-941-2)
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
- Signal word
- Warning
- Symbol(GHS)
- GHS06
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Uses & manufacturing
General Manufacturing Information2,4-Thiazolidinedione: ACTIVE
Applications
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
Downstream products
Related reactions
702 records
Compound notes
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