8726. Sorbose

Nomenclature

CAS number: 87-79-6
l-Sorbose; sorbin; sorbinose.
C6H12O6; mol wt 180.16.
C 40.00%, H 6.71%, O 53.28%.

Description and references

From sorbitol by fermentation with Acetobacter suboxydans: Perlman, J. Chem. Educ. 36, 60 (1959); Lockwood, Methods Carbohydr. Chem. 1, 151 (Academic Press, New York, 1962).

Chemical structure

Properties

Orthorhombic, bisphenoidal crystals. About as sweet as sucrose. d15 1.65. mp 165°. [α]D30 42.7° (c = 5). pKa (17.5° ): 11.55. Freely sol in water; almost insol in alcohol. Reduces Fehling's soln.

Use

In the manuf of vitamin C (accounts for nearly 1000 tons of ascorbic acid produced every year). For conversion of l-sorbose to 2-keto-l-gulonic acid see Reichstein, Grüssner, Helv. Chim. Acta 17, 311 (1934).