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Pent-2-en-1,5-disaeure
GLUTACONIC ACID · pentene diacid · pentenedioic acid · (E)-glutaconic acid · 2-PENTENEDIOIC ACID · TRANS-GLUTACONIC ACID · pent-2-ene-1,5-dioic acid · Glutaconic acid >=97.0% (T)
Identifikatoren & physikalische Daten
| CAS No. | 1724-02-3 |
|---|---|
| Summenformel | C5H6O4 |
| Durchschnittliche Molmasse | 130,1 g/mol |
| Monoisotopische Masse | 130,02660867 g/mol |
| SMILES | O=C(O)C=CCC(=O)O |
| InChIKey | XVOUMQNXTGKGMA-UHFFFAOYSA-N |
| PubChem CID | 74406 |
| DTXSID | DTXSID40862740 |
| Lokaler Name | Pent-2-en-1,5-disaeure |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 74,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 147 |
| Schmelzpunkt | 137-139 °C(lit.) |
| Siedepunkt | 413.8±28.0 °C(Predicted) |
| Dichte | 1.384±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Amber Vial, Refrigerator |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly) |
| pKa (Säurekonstante) | 4.21±0.10(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Beige |
| BRN | 1759560 |
| Stabilität | Light Sensitive |
| InChI | InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9) |
| InChIKey | XVOUMQNXTGKGMA-UHFFFAOYSA-N |
| SMILES | C(O)(=O)C=CCC(O)=O |
| LogP (Verteilungskoeffizient) | 0.040 (est) |
| CAS Datenbank | 1724-02-3(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Gesundheitliche Auswirkungen | Chronically high levels of glutaconic acid are associated with Glutaric Aciduria Type I. |
|---|---|
| Toxizitätsübersicht | Accumulating trans-glutaconic (TG) acids has been proposed to be involved in the development of the striatal degeneration seen in children with glutaric acidemia type 1 (GA1) via an excitotoxic mechanism. TG is neurotoxic and neurotoxicity is thought to be caused by an excitotoxic mechanism in which TG overactivates N-methyl-D-aspartate (NMDA) receptors. (A15451) In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage. (Wikipedia) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2917198090 |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Glutaconic acid has been used in the preparation of CoA-substrate glutaconyl-CoA by reacting with acetyl-CoA. It may be used in the preparation of 6-chloro-2(2H)-pyranone by reacting with phosphorus pentachloride (PCl5).