57410

Indole-3-propionic acid

≥97.0% (T)

• Synonym(s): NSC 3252, NSC 47831, 3-(3-Indolyl)propanoic acid, 3-(3-Indolyl)propionic acid, IPA
• Empirical Formula (Hill Notation): C₁₁H₁₁NO₂
• CAS Number: 830-96-6
• Molecular Weight: 189.21
• Beilstein/REAXYS Number: 147733
• EC Number: 212-600-1
• MDL number: MFCD00005660
• UNSPSC Code: 12352100
• PubChem Substance ID: 57651623
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: ≥97.0% (T)
• form: solid
• functional group: carboxylic acid
• SMILES string: OC(=O)CCc1c[nH]c2ccccc12
• 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)
• InChI key: GOLXRNDWAUTYKT-UHFFFAOYSA-N

Description

General description

Indole-3-propionic acid can be obtained from tryptophan by deamination reaction.

Application

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.

Biochem/physiol Actions

Studied as an adjunct to improve perfusion after liver transplant.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)