Xyloisosaccharinic acid

Xyloisosaccharinic acid [2,4-dihydroxy-2-(hydroxymethyl)butanoic acid] is one of the major, alkaline-degradation products of wood xylan, in particular, that of birch. The disaccharide, 2-O-D-xylopyranosyl-L-arabinose, which was isolated as a hydrolysis product of corn-cob hemicellulose, is readily degraded at 100° in 15 mM Ca(OH)2 to acidic products, primarily saccharinic acids. Xylan oligosaccharides from corn-cob hemicellulose produced 2,4-dihydroxy-2-(hydroxymethyl)buta-noic acid when exposed to 0.02 M Ca(OH)2 at 25°. However, it was noted that the xylan, itself, was stable at 100° in Af NaOH. The major acidic component of the hemicellulose fraction of slash pine Pinus el-liotti) after acid hydrolysis was identified as 4-O-methyl-D-glucuronic... 

R. Alen, Oxidation of xyloisosaccharinic acid by nitric acid, Carbohydr. Res., 154 (1986) 301-304. 

Fig. 7 -31. Peeling and stopping reactions of polysaccharides (Sjostrom, 1977). R = polysaccharide chain and R = CH2OH (cellulose and glucomannans) or H (xylan). Cellulose and glucomannans (R = CH2OH) (1) 3-Deoxyhexonic acid end groups (metasaccharinic acid), (2) 2-C-methylglyceric acid end groups, (3) 3-deoxy-2-C-hydroxymethylpentonic acid (glucoisosaccharinic acid), (4) 2-hydroxypropanoic acid (lactic acid), and (5) 3,4-dideoxypentonic acid (2,5-dihydroxypentanoic acid). Xylan (R = H) (3) 3-Deoxy-2-C-hydroxymethyltetronic acid (xyloisosaccharinic acid), (4) 2-hydroxypropanoic acid (lactic acid), and (5) 2-hydroxybutanoic acid. 1977. TAPPI. Reprinted from Tappi 60(9), p. 152, with permission.

Nitric acid oxidation of xyloisosaccharinic acid gives mainly... 

Lactone Dihydro-3-hydroxy-3-(hydroxymethyl)-2 (3Yi)-furanone. 3-Deoxy-2-C-hydroxymethyltetrono-1,4-lactone. Xyloisosaccharinic acid lactone [19444-86-1]... 

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