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

Göran Petersson (Institutionen för teknisk kemi)
Analytical Biochemistry Vol. 72 (1976), p. 623-628.
[Artikel, refereegranskad vetenskaplig]

Dehydroascorbic acid is shown to be converted to 2-(threo-1,2,3-trihydroxypropyl)tartronic acid in aqueous alkaline solutions. The structure of the acid was determined by mass spectrometry of its acyclic Me3Si 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 2,3-hexodiulosonic 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.


The study was made in parallel with technical alkaline treatments of various carbohydrates. This facilitated the determination of the degradation path and the new product from dehydroascorbic acid.

The renowned Nobel laureate Linus Pauling studied medical treatment with ascorbic acid by the time and thanked for the report in a personal letter.

More than 20 years later the author took up health aspects of antioxidants.



Denna post skapades 2010-01-21. Senast ändrad 2011-04-28.
CPL Pubid: 109937

 

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Institutioner (Chalmers)

Institutionen för teknisk kemi (1946-1998)

Ämnesområden

Analytisk kemi
Medicinsk bioteknologi (med inriktning mot cellbiologi)

Chalmers infrastruktur