| Identification | More | [Name]
3-Indolepropionic acid | [CAS]
830-96-6 | [Synonyms]
2-HYDROXYPROPANE
2-PPROPANOL
2-PROPANOL
3-(1H-INDOL-3-YL)PROPANOIC ACID
3-(1H-INDOL-3-YL)-PROPIONIC ACID
3-(3-INDOLYL)PROPANOIC ACID
3-(3-INDOLYL)-PROPIONIC ACID
3-INDOLEPROPIONIC ACID
AKOS BBS-00004245
AKOS BBS-00006584
DIMETHYLCARBINOL
FEMA 2929
INDOLE 3-PROPANOIC ACID
INDOLE-3-PROPIONIC ACID
INDOLEPROPIONIC ACID
IPA
ISOPROPANE
ISOPROPANO
ISOPROPANOL
ISOPROPANOL ALCOHOL | [EINECS(EC#)]
212-600-1 | [Molecular Formula]
C11H11NO2 | [MDL Number]
MFCD00005660 | [Molecular Weight]
189.21 | [MOL File]
830-96-6.mol |
| Chemical Properties | Back Directory | [Appearance]
pale yellow to yellow crystalline powder | [Melting point ]
~133 °C | [Boiling point ]
82 °C(lit.) | [density ]
0.960 g/mL at 20 °C
| [vapor density ]
2.1 (vs air)
| [vapor pressure ]
33 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.377(lit.)
| [Fp ]
53 °F
| [storage temp. ]
−20°C
| [solubility ]
ethanol: soluble50mg/mL, clear, yellow to orange | [form ]
crystalline
| [pka]
4.77±0.10(Predicted) | [color ]
light yellow
| [Water Solubility ]
slightly soluble | [Detection Methods]
T,NMR | [BRN ]
147733 | [CAS DataBase Reference]
830-96-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Indole-3-propionic acid(830-96-6) | [EPA Substance Registry System]
830-96-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R11:Highly Flammable.
R36:Irritating to the eyes.
R67:Vapors may cause drowsiness and dizziness.
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R10:Flammable. | [Safety Statements ]
S7:Keep container tightly closed .
S16:Keep away from sources of ignition-No smoking .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S37/39:Wear suitable gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
NM1329000 | [F ]
8-10-23 | [TSCA ]
Yes | [HS Code ]
29339990 | [Toxicity]
LDLo intraperitoneal in mouse: 100mg/kg |
| Hazard Information | Back Directory | [Description]
Indole-3-propionic acid is a bacterial metabolite that has antioxidant and neuroprotective activities.1,2,3 It scavenges ABTS (Item No. 27317) 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).2 Indole-3-propionic acid also decreases increases in MDA levels induced by amyloid β (1-42) (Item No. 20574) in PC12 cells.4 It decreases ischemia-induced increases in cell death of pyramidal neurons and levels of 4-hydroxy nonenal (HNE; Item No. 32100) and glial fibrillary acidic protein (GFAP) in the hippocampal CA1 region in gerbils when administered at a dose of 10 mg/kg per day.3 | [Chemical Properties]
pale yellow to yellow crystalline powder | [Uses]
Reactant for preparation of:
- Fluorescent analogues of strigolactones
- Anti-tumor agents
- Melanocortin receptors ligands
- Immunosuppressive agents
- Iinhibitors of hepatitis C virus
- Histamine H4 receptor agonists
- NR2B/NMDA receptor antagonists
- CB1 antagonist for the treatment of obesity
- Antibacterial agents
- Inhibitor of TGF-β receptor binding
Indole-3-propionic acid may be used in the synthesis of oxindole-3-propionic acid via reaction with N-bromosuccinimide in acetic acid followed by treatment with H2/Pd catalyst. | [Uses]
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. | [Synthesis Reference(s)]
Tetrahedron Letters, 25, p. 3159, 1984 DOI: 10.1016/S0040-4039(01)90997-9 | [General Description]
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. | [Biochem/physiol Actions]
Studied as an adjunct to improve perfusion after liver transplant. | [storage]
Store at -20°C | [Purification Methods]
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.] |
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