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An anhydroisosaccharinic acid obtained in large amounts by end-wise degradation of cellulose in alkaline media, and in small amounts in hydrolysates of cellulose, has been identified as a 1,4-anhydro-3-deoxypentitol-2-carboxylic acid (3-hydroxy-5-(hydroxymethyl)oxolane-3-carboxylic acid). Structural evidence was obtained by GC-MS studies of the compounds (as Me3Si derivatives) obtained on degradation of the acid to 1,4-anhydro-3-deoxypentitol by reduction of the methyl ester followed by periodate oxidation and borohydride reduction. In aqueous alkali, the acid is likely to be formed from a dicarbonyl precursor by benzilic acid rearrangement.

acta chemica scandinavica/acta chemica scandinavica. b, organic chemistry and biochemistry/acta chemica scandinavica. a, physical and inorganic chemistry/acta chemica scandinavica. series b. organic chemistry and biochemistry/acta chemica scandinavica. series a, physical and inorganic chemistry

Formation of 1,4-Anhydro-3-deoxypentitol-2-carboxylic Acids by Alkaline Degradation of Cellulose.