Conversion of dehydroascorbic acid to a branched hexaric acid in neutral and alkaline aqueous solution

✍ Scribed by Lars Löwendahl; Göran Petersson

• Publisher: Elsevier Science
• Year: 1976
• Tongue: English
• Weight: 360 KB
• Volume: 72
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(76)90575-3

✦ Synopsis

Dehydroascorbic acid is shown to be converted to 2-(threo-1,2,3-trihydroxypropylkartronic acid in aqueous alkaline solutions. The structure of the acid was determined by mass spectrometry of its acyclic Me,Si derivative. Mass spectrometric and chromatographic data are compared with those of related compounds. The acid is formed by a benzilic acid rearrangement of the intermediate 2,3hexodiulosonic acid. The rate of formation at 38°C was studied quantitatively by glc. It increases at increased alkalinity but is significant even at physiological pH. The presence of oxygen does not substantially influence the reaction.