83696-90-6

Basic information

• Product Name: 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID
• Synonyms: 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID;5-METHOXYINDOLE-3-BUTYRIC ACID;4-(5-methoxy-1H-indol-3-yl)butanoic acid;REF DUPL: 5-Methoxyindole-3-butyric acid;1H-Indole-3-butanoic acid, 5-methoxy-
• CAS NO: 83696-90-6
• Molecular Formula: C13H15NO3
• Molecular Weight: 233.26
• Product Categories: pharmacetical
• Mol File: 83696-90-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 458.9 °C at 760 mmHg
• Flash Point: 231.3 °C
• Appearance: /
• Density: 1.251 g/cm³
• Vapor Pressure: 3.24E-09mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID(83696-90-6)
• EPA Substance Registry System: 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID(83696-90-6)

Safety Data

• Hazardous Substances Data: 83696-90-6(Hazardous Substances Data)

Usage

General Description

4-(5-Methoxy-1H-indol-3-yl)-butyric acid, also known as 5-Methoxytryptophol or 5-Methoxyindole-3-butanoic acid, is a chemical compound that belongs to the class of indole alkaloids. It is derived from the amino acid tryptophan and is involved in various physiological functions, including the regulation of mood, sleep, appetite, and stress response. 4-(5-METHOXY-1H-INDOL-3-YL)-BUTYRIC ACID has been studied for its potential role in the treatment of depression, anxiety, and other mental health disorders. It is also a precursor to the hormone melatonin, which regulates the sleep-wake cycle. Additionally, 4-(5-Methoxy-1H-indol-3-yl)-butyric acid has been found to have antioxidant and anti-inflammatory properties, making it a subject of interest in the field of nutraceuticals and wellness products.

InChI:InChI=1/C13H15NO3/c1-17-10-5-6-12-11(7-10)9(8-14-12)3-2-4-13(15)16/h5-8,14H,2-4H2,1H3,(H,15,16)

Upstream product

• 83706-89-2 C₁₆H₂₀N₂O₄ 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 104-94-9 4-methoxy-aniline 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 27983-42-2 5-carboethoxypentanal 
• 83696-88-2 ethyl 4-(2-ethoxycarbonyl-5-methoxyindol-3-yl)butanoate 
• 83706-90-5 6-carboethoxy-6-p-methoxyphenylhydrazonohexanoic acid 
• 83706-89-2 ethyl 1-(4-methoxyphenylazo)-2-oxocyclohexanecarboxylate 
• 96-48-0 4-butanolide 
• 1006-94-6 5-methoxylindole 
• 83696-89-3 4-(2-carboxy-5-methoxyindol-3-yl)butanoic acid 

Downstream Products

• 13070-45-6 6-Methoxy-1,2,3,4-tetrahydrocarbazole 
• 143682-61-5 5-methoxy-3-[3-(1,2,3,6-tetrahydro-4-phenyl-1-pyridyl)butyl]indole 
• 112192-04-8 roxindole 
• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 

Relevant articles and documents

Deciphering DNA-based asymmetric catalysis through intramolecular Friedel-Crafts alkylations

We describe asymmetric intramolecular Friedel-Crafts alkylations with a DNA-based hybrid catalyst and propose a plausible binding model. This study shows promise for studying relationships between the helical chirality of DNA and enantioselectivity of the chemical reaction.

Electrophilic Substitution in Indoles. Part 11. The Mechanism of Substitution in 5-Methoxyindoles

Deuterium labelling experiments show that the boron trifluoride-catalysed cyclisation at 90 deg C of 4-(5-methoxyindole-3-yl)butanol (1e) to 6-methoxytetrahydrocarbazole (11a) occurs by two simultaneous pathways.The main route (83.5percent) involves initial cyclisation at the 3-position of (1e) to give an intermediate spirocyclic indolenine which then rearranges to the tetrahydrocarbazole.The minor pathway (16.5percent) involves direct attack at the 2-position.A similar duality of mechanism of substitution applies to the 6-methoxy-, 4,6-dimethoxy-, and 5,6-dimethoxy-indole analogues for which the extent of substitution at the 2-position can be correlated with the calculated change in ?-electron density at the 2- and 3-positions for a series of methoxy-substituted 3-methyl-indoles.These calculations do not, however, fit the experimental findings for the 5-methoxy-derivative which appears to be anomalous, showing an unexpectedly high percentage of direct substitution at the 2-position.A possible explanation of this result is advanced.