5745. Mannitol
Nomenclature
Description and references
Widespread in plants and plant exudates; obtained from manna and seaweeds: The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) pp 249-250. Forms a stable, equimolar compound with H2O2: S. Tanatar, J. Russ. Phys. Chem. Soc. 40, 376, C.A. 3, 883 (1909). Prepd by electrolytic reduction of glucose: Creighton, Can. Chem. Process Ind. 26, 690 (1942), C.A. 37, 10885 (1943); Wolfrom et al., J. Am. Chem. Soc. 68, 578 (1946). Prepn from seaweed: Sorensen, Kristensen, US 2516350 (1950); by hydrogenation of invert sugar, monosaccharides, and sucrose: Kasehagen, and Kasehagen, Luskin, US 2642462, US 2749371, and US 2759024 (1953, 1956, and 1956, all to Atlas Powder). Review of prepn: Pigman, loc. cit. Novel synthesis: M. Makkee et al., Chem. Commun. 1980, 930.
Properties
Orthorhombic needles from alc, mp 166-168°. Sweetish taste. d20 1.52. bp3.5 290-295°. Is inactive or very slightly levorotatory in distilled water. Forms sodium mannitoborate on addition of borax giving a greater rotation: [α]D20 +23° → +24° after 1 hr in a soln of 10 g mannitol +12.8 g borax + sufficient H2O to make 100 ml. One gram dissolves in ≈5.5 ml water, 83 ml alcohol; more sol in hot water. Insol in ether. Sol in pyridine, aniline, aq solns of alkalies. One gram dissolves in 18 ml glycerol (d 1.24). Soly tables: Creighton, Klauder, J. Franklin Inst. 195, 687 (1923). pKa (18°): 13.50.Use
Used with boric acid in the manuf of dry electrolytic condensers for radio applications; in making artificial resins and plasticizers; in pharmacy as excipient and diluent for solids and liqs. In analytical chemistry for boron determn; titrimetric determn of boric acid. In the manuf of mannitol hexanitrate. Used in the food industry as anticaking and free-flow agent, flavoring agent, lubricant and release agent, stabilizer and thickener and nutritive sweetener.Therapeutic Category
Diuretic. Diagnostic aid (renal function).
Keywords
Diagnostic Aid; Diuretic