Thiazolidinedione
THIAZOLIDINE-2,4-DIONE · TZD · Thiazolidinedione · 2,4-Thiazolidindione · U 25560 · idinedione · usafek-5496 · 2,4-ThiazoL
Identifiers & Physical Properties
| CAS No. | 2295-31-0 |
|---|---|
| Molecular formula | C3H3NO2S |
| Average molar mass | 117.13 g/mol |
| Monoisotopic mass | 116.98844934 g/mol |
| SMILES | O=C1CSC(=O)N1 |
| InChIKey | ZOBPZXTWZATXDG-UHFFFAOYSA-N |
| PubChem CID | 5437 |
| ChEMBL | CHEMBL85398 |
| ChEBI | CHEBI:50992 |
| EC No. | 218-941-2 |
| DTXSID | DTXSID5040623 |
Chemical & Physical Properties
| XLogP | 0.1 |
|---|---|
| Topological polar surface area | 71.5 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 122 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Melting point | 125-127 °C (lit.) |
| Boiling point | 178-179 °C (19 mmHg) |
| Density | 1.408 (estimate) |
| Vapor pressure | 0Pa at 25℃ |
| Refractive index | 1.5130 (estimate) |
| Flash point | 178-179°C/19mm |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | DMSO (Slightly), Methanol (Slightly)Soluble in water (30 mg/ml at 3°C), methanol, DMSO, ethanol, and ethyl ether. |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | 6.50±0.10(Predicted) |
| Color | Slightly yellow |
| BRN | 110700 |
| InChI | 1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) |
| InChIKey | ZOBPZXTWZATXDG-UHFFFAOYSA-N |
| SMILES | O=C1CSC(=O)N1 |
| LogP (partition coefficient) | -0.29 at 25℃ |
| CAS DataBase Reference | 2295-31-0(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | AA68LXK93C |
| NIST Chemistry Reference | 2,4-Thiazolidinedione(2295-31-0) |
| EPA Substance Registry System | 2,4-Thiazolidinedione (2295-31-0) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS06 |
| Signal word | Warning |
| GHS hazard statements | H301 |
| GHS precautionary statements | P264-P270-P301+P310a-P321-P405-P501a |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 24/25-36-26 |
| Water hazard class (WGK) | 3 |
| RTECS number | XJ5775000 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANT |
| Customs code | 29341000 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Inactive |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 15.4% (2 of 13) of reports.WarningH302 (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. |
|---|---|
| Regulatory information | Status: Cease Manufacture Update: 01-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19571 |
| Hazard Classes and Categories | Acute Tox. 4 (53.8%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | XJ5775000 |
| Customs code | 29341000 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS06 |
| Hazard symbols | Xi |
| Safety statements (S) | 24/25-36-26 |
| Hazard class | IRRITANT |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H301 |
| REACH registrations | Inactive |
| GHS precautionary statements | P264-P270-P301+P310a-P321-P405-P501a |
Applications & Uses
Uses
Inhibitor of enzyme
Uses
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.
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.