9030. d-Tagatose
Nomenclature
Description and references
Uncommon, but naturally occurring ketohexose. Isoln from Sterculia setigera gum: E. L. Hirst et al., J. Chem. Soc. 1949, 3145. Prepn from d-galactose: C. A. L. De Bruyn, W. A. Van Ekenstein, Rec. Trav. Chim. 16, 262 (1897); T. Reichstein, W. Bosshard, Helv. Chim. Acta 17, 753 (1934); by biochemical oxidation of d-talitol: E. L. Totton, H. A. Lardy, J. Am. Chem. Soc. 71, 3076 (1949); from lactose in heated milk: S. Adachi, Nature 181, 840 (1958). Synthesis: M. L. Wolfrom, R. B. Bennett, J. Org. Chem. 30, 1284 (1965); A. A. H. Al-Jobore et al., Carbohydr. Res. 16, 474 (1971). Crystal structure: S. Takagi, R. D. Rosenstein, ibid. 11, 156 (1969). Manuf process from whey: J. R. Beadle et al., US 5002612 (1991 to Biospherics). Stability and sweetening properties in toothpaste: Y. Lu, Int. J. Cosmet. Sci. 23, 175 (2001). Review of use as bulk sugar substitute: G. V. Levin et al., Am. J. Clin. Nutr. 62, Suppl., 1161S-1168S (1995). Series of articles on toxicology and gastrointestinal tolerance: Regul. Toxicol. Pharmacol. 29, S1-S93 (1999).
Properties
Crystals from aq ethanol, mp 131-133°. [α]D25 5° (c = 1 in water). Sucrose-like taste, approx 92% as sweet as sucrose.Derivative
l-Tagatose.Nomenclature
Description and references
Prepn: C. Glatthaar, T. Reichstein, Helv. Chim. Acta 20, 1537 (1937). Stereoselective synthesis: T. Mukaiyama et al., Chem. Lett. 1982, 1169.