4273. Fructose
Nomenclature
Description and references
Occurs in a large number of fruits, honey, and as the sole sugar in bull and human semen: Auerbach, Bodlander, Angew. Chem. 36, 602 (1923); Mann, Nature 157, 79 (1946); Pryde, ibid. 660. Prepd by adding abs alcohol to the syrup obtained from the acid hydrolysis of inulin: Bates et al., Natl. Bur. Stand. Circ. C440, 399 (1942). Prepn from dextrose: Cantor, Hobbs, US 2354664 (1944 to Corn Prod. Refining). From sucrose by enzymatic conversion: Koepsell et al., US 2729587 (1956 to U.S.A.). Crystal and molecular structure: J. A. Kanters et al., Acta Crystallogr. B33, 665 (1977). Review: Barry, Honeyman, Adv. Carbohydr. Chem. 7, 53-98 (1952); M. Chen, R. L. Whistler, ibid. 34, 285-343 (1977). Occurs in both the furanose and pyranose forms. An aq soln at 20° contains about 20% of the furanose form.
Properties
Orthorhombic, bisphenoidal prisms from alc, dec 103-105°. Sweetest of the sugars. Shows mutarotation. [α]D20 132° to 92° (c = 2). Rapid and anomalous mutarotation involves pyranose-furanose interconversion. The final value is obtained instantly in the presence of hydroxyl ions. pKa (18°): 12.06. Freely sol in water. One gram dissolves in 15 ml alc, in 14 ml methanol. Slightly sol in cold, freely in hot acetone; sol in pyridine, ethylamine, methylamine.Derivative
Ferric Form.Nomenclature
Description and references
Prepn: Stitt et al., Proc. Soc. Exp. Biol. Med. 110, 70 (1962); Saltman, Charley, US 3074927 and US 3275514 (1966).
Use
To prevent sandiness in ice cream.Therapeutic Category
Fluid and nutrient replenisher, and ferric form as hematinic.
Therapeutic Category (Veterinary)
For bovine ketosis.Keywords
Ferric Fructose: Hematinic