HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
(+-)-2-Hydroxyglutaric acid
2-hydroxyglutarate · C02630 · α-Hydroxyglutaric Acid · alpha-hydroxyglutarate · a-Hydroxyglutaric Acid · 2,3-Dideoxypentaric Acid · DL-2-Hydroxyglutaric Acid
Identifikatoren & physikalische Daten
| CAS No. | 2889-31-8 |
|---|---|
| Summenformel | C5H8O5 |
| Durchschnittliche Molmasse | 148,11 g/mol |
| Monoisotopische Masse | 148,03717336 g/mol |
| SMILES | O=C(O)CCC(O)C(=O)O |
| InChIKey | HWXBTNAVRSUOJR-UHFFFAOYSA-N |
| PubChem CID | 43 |
| ChEMBL | CHEMBL4870693 |
| ChEBI | CHEBI:17084 |
| DTXSID | DTXSID40864360 |
Chemische & physikalische Eigenschaften
| XLogP | -1 |
|---|---|
| Polarare Oberfläche (TPSA) | 94,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 141 |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105] |
| Physical Description | Solid |
| Schmelzpunkt | 98-100 °C(Solv: ethyl acetate (141-78-6)) |
| Siedepunkt | 394.2±27.0 °C(Predicted) |
| Dichte | 1.508±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 3.67±0.10(Predicted) |
| Farbe | Colorless to light yellow |
Sicherheit & Vorschriften
| Gesundheitliche Auswirkungen | High 2-Hydroxyglutarate levels are associated with gliomas and acute myeloid leukemia. L-2-Hydroxyglutarate can reversibly promote leukemogenesis in vitro. Chronically high levels of L-2-hydroxyglutaric acid are associated with the inborn error of metabolism called: D-2-Hydroxyglutaric Aciduria. The D form is rare, with symptoms including macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. |
|---|---|
| Expositionspfade | Endogenous, Ingestion |
| Toxizitätsübersicht | 2-hydroxyglutarate is an oncometabolite. It is a competitive inhibitor of multiple α-ketoglutarate-dependent dioxygenases, including histone demethylases and the TET family of 5-methlycytosine (5mC) hydroxylases. As a result, high levels of 2-hydroxyglutarate lead to genome-wide histone and DNA methylation alterations, which in turn lead to mutations that ultimately cause cancer. High L-2-Hydroxyglutarate levels are associated with gliomas and acute myeloid leukemia. L-2-Hydroxyglutarate can reversibly promote leukemogenesis in vitro. D-2-hydroxyglutarate mediates its neurotoxicity through activation of N-methyl-D-aspartate receptors. D-2-hydroxyglutarate is structurally similar to the excitatory amino acid glutamate and stimulates neurodegeneration by mechanisms well-known for glutamate, NMDA or mitochondrial toxins (A15198). |
| Signs and Symptoms | Symptoms of chronic exposure to D-2-Hydroxyglutarate include macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. |
| Carcinogen Classification | Not listed by IARC. Has been implicated in oncogenesis (A15091, A15090, A15088). |
| Alarmwort | Achtung |
| Gefahrenhinweise | Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H225 |
Anwendungen & Verwendung
Verwenden
A potential inhibitor of glutamate carboxypeptidase.