18070-61-6

Basic information

• Product Name: 1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid
• CAS NO: 18070-61-6
• Molecular Formula: C₁₄H₁₄N₂O₄
• Molecular Weight: 274.272
• Mol File: 18070-61-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 595.5°C at 760 mmHg
• Flash Point: 314°C
• Density: 1.461g/cm³
• Vapor Pressure: 4.97E-15mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid(18070-61-6)
• EPA Substance Registry System: 1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid(18070-61-6)

Safety Data

• Hazardous Substances Data: 18070-61-6(Hazardous Substances Data)

Usage

Chemical structure

1-Methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid is a beta-carboline derivative with a methyl group at the 1-position, and carboxylic acid groups at the 1 and 3 positions.

Derivation

The compound is derived from the tryptophan metabolism pathway.

Biological processes

It has been implicated in various biological processes, including neurotransmission, neurotoxicity, and the regulation of mood and behavior.

Neurodegenerative diseases

The compound has been studied for its potential role in the progression of neurodegenerative diseases such as Parkinson's and Alzheimer's.

Therapeutic applications

1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-1,3-dicarboxylic acid has been investigated for its potential therapeutic applications, particularly in the development of new drugs for the treatment of neurological disorders and psychiatric conditions.

Upstream product

• 73-22-3 L-tryptophan 
• 127-17-3 2-oxo-propionic acid 
• 73-22-3 L-Tryptophan 

Downstream Products

• 39537-10-5 (S)-6 
• 40678-46-4 (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 

Relevant articles and documents

HPLC-MS/MS Profiling of Tryptophan-Derived Alkaloids in Food: Identification of Tetrahydro-β-carbolinedicarboxylic Acids

A method for selective detection of 1,2,3,4-tetrahydro-β-carbolinecarboxylic acids (THCCs) was developed based on electrospray ionization-tandem mass spectrometry coupled to liquid chromatography (HPLC-ESI-MS/MS). Low-energy collision-induced dissociation (CID) led to characteristic fragment ions due to neutral loss of 73 amu. Subsequently, constant neutral loss scanning was used for substructure specific screening of THCCs in food samples. Detection limits for HPLC-ESI-MS/MS analysis of THCCs applying neutral loss experiments were established at 100 ng mL-1 (ca. 2.5 pmol on column). Application of this MS/MS method enabled us to detect THCC derivatives derived from Pictet-Spengler condensation of tryptophan with α-oxo acids. Subsequently, diastereomeric 1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid 3a/b, 1-methyl-1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid 4a/b, and 1-(2′-carboxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 5a/b were identified in alcoholic beverages, seasoning sauces, yeast extract, and fruit products for the first time. Most food samples under study contained 3a/b and 4a/b in significant amounts. 5a/b was identified in soy sauce, worcestershire sauce, seasoning sauce, and yeast extract. Due to the excellent selectivity of tandem mass spectrometry coeluting tetrahydroβ-carboline derivatives could be identified unequivocally by HPLC-ESI-MS/MS.

Electrochemistry of Natural Products. 7. Oxidative Decarboxylation of Some Tetrahydro-β-carbolinecarboxylic Acids

A series of 1,2,3,4-tetrahydro-β-carboline-1- and -3-carboxylic acids containing various substituents in positions 1, 2, and 3 were oxidized electrochemically.In general, the acids were decarboxylated, and unsaturation was introduced into the C ring.The oxidation appears to take place through the indole ring nitrogen, and possible mechanisms of the reactions are presented.Parallels between the observed reactions and early steps in indole alkaloid biosynthesis are discussed.The oxidative dimerization of tetrahydrocarbazole is reported.