SUMMARY 1. It is shown by means of filter-paper chromatograms prepared at intervals during the oxidation of quinic acid by hydrogen peroxide that at least six acids appear in the reaction liquid. 2. One of these acids is shown to be citric acid, and the oxidation of citric acid is shown to account for a further two of the acids resulting from the oxidation of quinic acid. 3. After prolonged oxidation (by H2O2) of both quinic and citric acids one acid predominates. This acid is proved by isolation and characterization to be malonic acid. 4. Evidence is produced which suggests that acetonedicarboxylic acid is an intermediate in the oxidation of citric acid (and, therefore, of quinic acid) to malonic acid. IN the course of the isolation and identification of quinic acid from the young fruits of the Worcester Pearmain apple, filter-paper chromatograms were run at intervals during the oxidation of the quinic acid with hot H2O2 (Hulme, 1951). These chromatograms showed that, while the reaction as a whole is a complex one involving at least six acids in addition to the original quinic acid, two acids emerged as the main products of the reaction. One of these was found to be citric acid, which was the acid obtained by Fischer and Dangschat (1934) on oxidation of quinic acid by periodic acid followed by bromine water. The work described in the present paper was carried out primarily to identify the second acid. The results also illustrate the value of paper chromatography in following the course of a complex series of reactions. The large amount of quinic acid present in young apples—recent work has shown that young Worcester Pearmain apples (average weight 15 g.) contain rather more quinic than malic acid—poses the question of its function in the metabolism of the fruit as indeed in other plant tissues where it is known to exist. For this reason a more complete knowledge of its chemistry is desirable than at present exists. Small-scale oxidations (~ 20 mg. quinic acid and 1 ml. 100 vol. H2O2) yield, as oxidation proceeds, chromatograms having the patterns shown in Fig. 1. Fig. 2 (upper portion) is a photograph of a chromatogram taken after 25-30 hours' oxidation in the large-scale preparative experiment to be described later; it is included to show the streaking effect produced by the continuous state of flux of the system. Although it does not follow that the acid-reacting spots on the chromatogram represent a sequence of events commencing at the acid of lowest RF—during
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