6639-06-1

Basic information

• Product Name: 1-INDOLEPROPIONIC ACID
• Synonyms: BETA-N-INDOLE PROPIONIC ACID;B-N-INDOLEPROPIONIC ACID;3-(1H-INDOL-1-YL)PROPANOIC ACID;1-INDOLEPROPIONIC ACID;1H-indole-1-propanoic acid;3-(1-indolyl)propanoic acid;3-indol-1-ylpropanoic acid;3-indol-1-ylpropionic acid
• CAS NO: 6639-06-1
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• EINECS: 229-643-7
• Mol File: 6639-06-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 396.5°C at 760 mmHg
• Flash Point: 193.6°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 5.34E-07mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-INDOLEPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-INDOLEPROPIONIC ACID(6639-06-1)
• EPA Substance Registry System: 1-INDOLEPROPIONIC ACID(6639-06-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6639-06-1(Hazardous Substances Data)

Usage

General Description

1-Indolepropionic acid is a molecule belonging to the class of indole derivatives. It is a natural compound found in the human body and in certain foods, such as cow's milk and fermented food products. Research has shown that 1-indolepropionic acid has potential health benefits, particularly in relation to its anti-inflammatory and anti-oxidative properties. It is also being investigated for its potential role in promoting gut health and supporting the immune system. Additionally, there is ongoing interest in studying its potential therapeutic effects on conditions such as diabetes, obesity, and neurodegenerative diseases. Overall, 1-indolepropionic acid shows promise as a bioactive compound with various potential health applications.

InChI:InChI=1/C11H11NO2/c13-11(14)6-8-12-7-5-9-3-1-2-4-10(9)12/h1-5,7H,6,8H2,(H,13,14)

Upstream product

• 120-72-9 indole 
• 79-10-7 acrylic acid 
• 109-78-4 3-Hydroxypropionitrile 
• 140-88-5 ethyl acrylate 
• 4414-79-3 3-(1H-indol-1-yl)propanenitrile 
• 76916-49-9 3-(indol-1-yl)propionic acid methyl ester 
• 221687-62-3 methyl 3-(1H-indol-1-yl)-2-methylpropanoate 
• 3395-91-3 Methyl 3-bromopropionate 
• 26585-38-6 3-(indol-1-yl)propionic acid ethyl ester 

Downstream Products

• 81250-90-0 3-(2,3-dioxoindolin-1-yl)propanoic acid 
• 351015-67-3 1-(3-hydroxypropyl)-1H-indole-3-carbaldehyde 

Relevant articles and documents

Computational and experimental studies of (2,2)-Bis(indol-1-yl- methyl)acetate suggest the importance of the hydrophobic effect in aromatic stacking interactions

To understand the driving forces of aromatic stacking interactions in water, we have performed conformational searches, molecular dynamics simulations, potential of mean force (PMF) and free energy perturbation (FEP) calculations, syntheses, and NMR studies on sodium (2,2)-bis(indol-1-yl- methyl)acetate (1), sodium 3-indol-1-yl-2-methyl-propionate (2), and sodium 3-indol-1-yl-propionate (3). The conformational searches on 1 revealed that the isobutyric acid linker of 1 allows the molecule to adopt the tilted T- shaped stacked, off-center stacked, face-to-face stacked, and nonstacked conformations in a vacuum. The PMF and FEP calculations suggested that the most thermodynamically stable conformers in water are the tilted T-shaped stacked and nonstacked conformers. Independent NMR spectroscopic studies of 1-3 revealed that both the tilted T-shaped stacked and nonstacked conformers are populated in D2O and in d6-DMSO, and they are in a rapid equilibrium. Furthermore, the NMR studies found (i) a larger population of the tilted T, shaped stacked conformation of 1 at 22 °C in D2O than in d6-DMSO and (ii) more different populated stacked conformations of 1 at 60 °C in D2O than in d6-DMSO. One would expect larger populations of the stacked conformations in d6-DMSO, whose dielectric constant is smaller than that of water, if the electrostatic interaction were the only driving force of the aromatic stacking interactions. The results, therefore, suggest that the hydrophobic effect plays an important role in the stacking interaction of 1 in water.

CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF

The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.

Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists

A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit 1. The dihydroindolyl glycinamide 10a significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide 12c also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both compounds 10a and 12c represent potential tools for further investigation into the biology of the NPY5 receptor.