252340-31-1

Basic information

• Product Name: cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• CAS NO: 252340-31-1
• Molecular Weight: 366.371
• Mol File: 252340-31-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(252340-31-1)
• EPA Substance Registry System: cis-(1R,3S)-1-(1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(252340-31-1)

Safety Data

• Hazardous Substances Data: 252340-31-1(Hazardous Substances Data)

Upstream product

• 50-99-7 D-glucose 
• 32450-62-7 sodium (2S)-2-amino-3-(1H-indol-3-yl)propanoate 
• 73-22-3 L-Tryptophan 

Relevant articles and documents

Formation of tetrahydro-β-carbolines and β-carbolines during the reaction of L-tryptophan with D-glucose

The reaction of L-tryptophan (Trp) with D-glucose under conditions that can occur during food processing and preparation was studied by high- performance liquid chromatography with diode array detection (HPLC/DAD). Besides the well-established glucose-tryptophan Amadori product (AP), (1R,3S)-1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-1,2,3,4-tetrahydro-β- carboline-3-carboxylic acid (PHP-THβC) was identified as an important product of this reaction. For preparation, PHPTHβC was obtained in high yields when Trp and D-glucose were reacted under strongly acidic conditions after heating in methanol. At elevated reaction temperatures (150 °C) 1- acetyl-β-carboline (acetyl-βC), was detected in significant concentrations. The mixtures were heated under variations of reaction time and temperature, and AP, PHP-THβC, and acetyl-βC were quantified. In the presence of air oxygen or mild, food relevant oxidants, such as L-dehydroascorbic acid, PHP- THβC was readily oxidized to a product that was identified as the previously unknown 1-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-β-carboline (PHP-βC). Formation of PHP-THβC and PHP-βC in foodstuffs would deserve particular interest because multiple physiological activity of THβC and βC derivatives has been shown previously.