3-(Indol-3-yl)propionsure Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R11:Leichtentzündlich.
R36:Reizt die Augen.
R67:D?mpfe k?nnen Schl?frigkeit und Benommenheit verursachen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitssch?dlich beim Verschlucken.
R10:Entzündlich.
S-S?tze Betriebsanweisung:
S7:Beh?lter dicht geschlossen halten.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S22:Staub nicht einatmen.
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 (IC
50 = 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.
Chemische Eigenschaften
pale yellow to yellow crystalline powder
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.
Definition
ChEBI: An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.
Allgemeine Beschreibung
3-Indolepropionic acid is an effective inhibitor of aggregation of misfolded β-amyloid protein (Abeta). Three-component one-pot procedure has been reported to assemble 3-indolepropionic acids.
Synthese
3-Indolepropionic acid is mainly prepared by reacting indole with acrylic acid and acetic anhydride under heating and stirring conditions, first generating an intermediate of acetyl indole-3-propionic acid. Subsequently, this ester intermediate is subjected to alkaline hydrolysis (e.g., using an aqueous sodium hydroxide solution) to remove the acetyl group and hydrolyze the ester bond. Finally, an acidification step yields the target product, 3-indolepropionic acid.
l?uterung methode
Recrystallise it from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. The picrate has m 143-144o, and the methyl ester crystallises from *C6H6 or MeOH with m 81-83o. [Beilstein 22 III/IV 1113, 22/3 V 114.]
3-(Indol-3-yl)propionsure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
