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Formation of 1,4-anhydro-3-deoxypentitol-2-carboxylic acids by alkaline degradation of cellulose

Göran Petersson (Institutionen för teknisk kemi) ; Olof Samuelson (Institutionen för teknisk kemi)
Acta Chemica Scandinavica B Vol. 30 (1976), p. 27-30.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: structure determination by mass spectrometry

The acid had been observed as a degradation product from carbohydrates in many studies during several years. It was known as Alfredo´s acid at the department before this assessment of its structure.

Denna post skapades 2010-02-10. Senast ändrad 2010-10-31.
CPL Pubid: 111866


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