3-(Indol-3-yl)propionsure
1H-Indole-3-propanoic acid
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Grundinformationen
- CAS
830-96-6- Standard-SMILES
O=C(O)CCc1c[nH]c2ccccc12- InChIKey
GOLXRNDWAUTYKT-UHFFFAOYSA-N- Summenformel
- C11H11NO2
- Durchschnittliche Molmasse
- 189,21 g/mol
- Monoisotopische Masse
- 189,07897859
Überblick
3-(1H-indol-3-yl)propanoic acid is an indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3. It has a role as an auxin, a plant metabolite and a human metabolite. It is functionally related to a propionic acid. It is a conjugate acid of a 3-(1H-indol-3-yl)propanoate.
Namen und Bezeichner
- Bevorzugter Name
- 1H-Indole-3-propanoic acid
- IUPAC
- 3-(1H-indol-3-yl)propanoic acid
- Lokaler Name
- 3-(Indol-3-yl)propionsure
- Englischer Name
- 3-Indolepropionic acid
- Summenformel
- C11H11NO2
- Molmasse
- 189.21
Namen und Synonyme
3-Indolepropionic acid830-96-6Indole-3-propionic acid1H-Indole-3-propanoic acidIndolepropionic acid3-(3-Indolyl)propionic acid3-(3-Indolyl)propanoic acidOxigon3-(Indol-3-yl)propionic acid1H-INDOLE-3-PROPIONIC ACID3-(3-Indole)propionic acidbeta-(3-Indolyl)propionic acid
Weitere Namen anzeigen
PROPAN-2-OL3-(1H-INDOL-3-YL)PROPANOIC ACIDISOPROPYL ALCOHOISOPROPANEFEMA 2929ISOPROPANOISOPROPANOL ALCOHOL2-PPROPANOL
3-Indolepropionicacidindole-3-propanoic acidJF49U1Q7KN1H-Indole-3-proponoic acidVP-20629NSC-3252NSC-47831SHP622
Datenbank-Bezeichner
- CAS
830-96-6- PubChem CID
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 53,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 217
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.75
Melting Point134 - 135 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 133 °C · ~133 °C
- Siedepunkt
- 82 °C · 82 °C(lit.)
- Dichte
- 0.96 g/mL · 0.960 g/mL at 20 °C
- Dampfdichte
- 2.1 · 2.1 (vs air)
- Dampfdruck
- 33 mm · 33 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.377(lit.)
- Flammpunkt
- 53 °F · 53 °F
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- 50 mg/mL, · ethanol: soluble50mg/mL, clear, yellow to orange
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 18.2% (2 of 11) of reports.
Warning
H302 (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.
Gefahrenhinweise
Regulatory Information1H-Indole-3-propanoic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (18.2%)
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339990
- RTECS-Nr.
- NM1329000
- risk_code
- 22-36/37/38
- Toxizität
- LDLo intraperitoneal in mouse: 100mg/kg
- hazard_code
- Xi
- safety_code
- 26-37/39
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsMembrane
Verwendung und Herstellung
General Manufacturing Information1H-Indole-3-propanoic acid: INACTIVE
Anwendungen
Beschreibung3-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.
Verwenden3-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.
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