3-(Indol-3-yl)propionsure
PROPAN-2-OL · INDOLE-3-PROPIONIC ACID · 3-(1H-INDOL-3-YL)PROPANOIC ACID · ISOPROPYL ALCOHO · ISOPROPANE · FEMA 2929 · ISOPROPANO · ISOPROPANOL ALCOHOL
Identifikatoren & physikalische Daten
| CAS No. | 830-96-6 |
|---|---|
| Summenformel | C11H11NO2 |
| Durchschnittliche Molmasse | 189,21 g/mol |
| Monoisotopische Masse | 189,07897859 g/mol |
| SMILES | O=C(O)CCc1c[nH]c2ccccc12 |
| InChIKey | GOLXRNDWAUTYKT-UHFFFAOYSA-N |
| PubChem CID | 3744 |
| ChEMBL | CHEMBL207225 |
| ChEBI | CHEBI:43580 |
| EC No. | 212-600-1 |
| DTXSID | DTXSID7061192 |
| Lokaler Name | 3-(Indol-3-yl)propionsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 53,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 217 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 1.75 |
| Schmelzpunkt | 134 - 135 °C~133 °C |
| Physical Description | Solid |
| Siedepunkt | 82 °C(lit.) |
| Dichte | 0.960 g/mL at 20 °C |
| Dampfdichte | 2.1 (vs air) |
| Dampfdruck | 33 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.377(lit.) |
| Flammpunkt | 53 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | ethanol: soluble50mg/mL, clear, yellow to orangeslightly soluble |
| pKa (Säurekonstante) | 4.77±0.10(Predicted) |
| Aggregatzustand | crystalline |
| Farbe | light yellow |
| BRN | 147733 |
| InChI | 1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14) |
| InChIKey | GOLXRNDWAUTYKT-UHFFFAOYSA-N |
| SMILES | OC(=O)CCc1c[nH]c2ccccc12 |
| CAS Datenbank | 830-96-6(CAS DataBase Reference) |
| NIST chemische Informationen | Indole-3-propionic acid(830-96-6) |
| EPA chemische Informationen | 1H-Indole-3-propanoic acid (830-96-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 18.2% (2 of 11) of reports.WarningH302 (18.2%): 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 11 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | 1H-Indole-3-propanoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (18.2%) |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29339990 |
| RTECS-Nr. | NM1329000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | LDLo intraperitoneal in mouse: 100mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-37/39 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
3-Indolepropionic acid is a bacterial metabolite that has antioxidant and neuroprotective activities. It scavenges ABTS radicals in a cell-free assay when used at concentrations ranging from 50 to 150 μM and decreases hydrogen peroxide-induced malondialdehyde (MDA) levels in rat striatal membranes (IC50 = 180 μM). Indole-3-propionic acid also decreases increases in MDA levels induced by amyloid β (1-42) in PC12 cells. It decreases ischemia-induced increases in cell death of pyramidal neurons and levels of 4-hydroxy nonenal (HNE; ) and glial fibrillary acidic protein (GFAP) in the hippocampal CA1 region in gerbils when administered at a dose of 10 mg/kg per day.
Verwenden
3-Indolepropionic acid is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland.