The Oxidative Degradation of ʟ-Ascorbic Acid via an α-Ketoaldehyde

Open Access

1 December 1982

journal article
Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung C

Vol. 37 (11-12) , 1064-1069
https://doi.org/10.1515/znc-1982-11-1203

Abstract

Dehydro-ʟ-ascorbic acid, the oxidation product of L-ascorbic acid, is unstable in aqueous solution and decomposed by a hydrolytic disruption of its ring structure to 2,3-diketo-ʟ-gulonic acid. It is shown by means of UV, ¹H-, and ¹³C-NMR spectroscopy that after decarboxylation 3,4,5-trihydroxy-2-keto-ʟ-valeraldehyde, an α-ketoaldehyde, is formed. This substance is oxidized further to ʟ-erythroascorbic acid, coupled with a reduction of 2,3-diketo-ʟ-gulonic acid to L-ascorbic acid.

Keywords

ʟ-ASCORBIC ACID
DEHYDRO-ʟ-ASCORBIC ACID
Α-KETOALDEHYDE
ʟ-ERYTHROASCORBIC ACID
NMR

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