Formation of 1,4-anhydro-3-deoxypentitol-2-carboxylic acids by alkaline degradation of cellulose
Artikel i vetenskaplig tidskrift, 1976

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.

structure determination by mass spectrometry


Göran Petersson

Institutionen för teknisk kemi

Olof Samuelson

Institutionen för teknisk kemi

Acta Chemica Scandinavica B

Vol. 30 27-30


Analytisk kemi

Organisk kemi

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