630392-83-5

Basic information

• Product Name: (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID
• Synonyms: (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID;(S)-2-AMINO-2-(1H-INDOL-3-YL)ACETIC ACID
• CAS NO: 630392-83-5
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• Product Categories: pharmacetical
• Mol File: 630392-83-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 438.6°C at 760 mmHg
• Flash Point: 219°C
• Appearance: /
• Density: 1.422g/cm³
• Vapor Pressure: 1.82E-08mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID(630392-83-5)
• EPA Substance Registry System: (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID(630392-83-5)

Safety Data

• Hazardous Substances Data: 630392-83-5(Hazardous Substances Data)

Usage

General Description

(S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID is a chemical compound that consists of an amino group attached to the carbon-3 of an indole ring and an acetic acid moiety. It is a derivative of the amino acid tryptophan and is commonly used in the synthesis of various pharmaceuticals and research chemicals. (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID has been studied for its potential role in regulating serotonin levels in the brain and has been investigated for its potential use in treating various mental health disorders such as depression and anxiety. Additionally, (S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID has been found to exhibit antioxidant and neuroprotective properties, making it a subject of interest in the field of neuropharmacology.

InChI:InChI=1/C10H10N2O2/c11-9(10(13)14)7-5-12-8-4-2-1-3-6(7)8/h1-5,9,12H,11H2,(H,13,14)/t9-/m0/s1

Upstream product

• 120-72-9 indole 
• 1031436-76-6 3-indolylglycine ethyl ester 

Downstream Products

• 1217312-32-7 C₂₀H₁₄N₂O₄ 

Relevant articles and documents

Indolylglycines Backbones in the Synthesis of Enantiopure 3,3-Spiroindolenines, Indolyl Tetracyclic Hemiaminals, and 3-Indolyl-maleimides Frameworks

This paper describes the synthesis of novel N-substituted 3-indolylglycines (3IGs), in high yields and optical purity via three-component Mannich reaction (3CR) of indole and free glyoxylic acid in the presence of primary and secondary aliphatic amines. By using this efficient approach, a series of racemic 3-indolylglycines (3IGs) as well as the optically pure (S)-3-indolylglycine ((S)-3IG) in multigram synthesis using (R-1-phenylethylamine ((R)-α-PEA) as chiral pool were synthetized. In parallel investigations, 3IGs were used as the starting material for the highly stereoselective synthesis of spiroindolenines bearing three controlled contiguous stereogenic centers. Despite our expectations, the N-chloroacetyl esters of 3IGs did not provide the expected spiroindolenine derivatives but led us to the discovery of a new methodology for the preparation of 3-indolylmaleimides (3IMs); compounds known for their broad range of important biological and fluorescence activities.

Lithium chloride-assisted selective hydrolysis of methyl esters under microwave irradiation

A rapid and mild method for the selective hydrolysis of methyl ester in lithium chloride-N,N-dimethylformamide (LiCl-DMF) system under microwave irradiation has been developed. The effects of substituent, metal salt, and solvent on the reactivity and selectivity of the hydrolysis reaction have been investigated. Microwave irradiation significantly improves the reaction yield within a short time in an LiCl-DMF system. Moreover, the chiral-carbon of methyl esters retained its configuration during the reaction. Finally, the catalytic mechanism of hydrolysis by LiCl salt has also been proposed.

Scope and limitations of sodium and potassium trimethylsilanolate as reagents for conversion of esters to carboxylic acids

Sodium or potassium trimethylsilanolate act as versatile and very powerful reagents for conversion of a wide variety of esters to carboxylic acids. The reactions were performed in tetrahydrofuran under mild reaction conditions with high to quantitative yields.