Hexitols

Hexitols

 

hexahydric acyclic alcohols, HOCH2(CHOH)4-CH2OH; colorless crystalline substances with a sweet taste. Readily soluble in water and alcohol; insoluble in ether. The hexitols contain four asymmetric carbon atoms and exist as ten stereoisomers that may be obtained by reduction of hexoses. Hexitols are easily esterified; oxidation leads to hexoses and sugar acids. Some hexitols (D-mannitol, D-sorbitol, dulcitol, and D-iditol) are encountered in nature.

D-mannitol (I). Melting point, 166°C; boiling point, 276°-280° C/133.322 newtons per sq m (that is, 1 mm Hg); specific rotation [α]Hexitols = -0.244° (water). It is found in the solidified sap of the Transcaucasian ash (so-called manna), as well as in marine algae, fungi, olives, and other plants. In industry, D-mannitol is produced from marine brown algae or catalytic hydrogenation of saccharose. It is the starting material in the production of surface-active agents, drying oils, resins, and lacquer and is also used in the foodstuffs and pharmaceutical industries and in perfume manufacture.

D-sorbitol (II). Melting point, 110°-111°C (anhydrous); [α]Hexitols = − 1.73° (water); it is found in large quantities in algae, mountain ash, and other plants. D-sorbitol is obtained by catalytic or electrolytic reduction of D-glucose.

D-sorbitol is a major intermediate product in the production of ascorbic acid; it is also used as a substitute for sugar for persons suffering from sugar diabetes.

Dulcitol. Melting point, 188.5° C. Found in marine algae and in yeast. It can be produced synthetically by reduction of D-galactose by sodium amalgam. Dulcitol is a component of mediums used in bacteriological studies.

D-iditol. Melting point, 73° C. Found in the berries of the mountain ash together with sorbitol.

References in periodicals archive ?
Investigation on the mechanism by fructose, hexitols and other compounds regulate the translocation of glucokinase in rat hepatocytes.
Recently, it has been proposed that hexitols present in sugarless chewing gums might also be playing a role in the amelioration of POI because these are known to cause gastrointestinal symptoms such as gas, bloating, and abdominal cramps in a dose-dependent manner.
The patent is named 'Method of Synthesis of Substituted Hexitols Such as Dianydrogalactitol' and has a patent term that lasts until 2030.
In addition, sugar free chewing gum that contains the artificial sweetener sorbitol and other hexitols might be having side effects such as bloating, gas, and abdominal cramps.
Because it is difficult to exclude the presence of other six-carbon polyols solely on the retention times on the HPLC column, we used 1H- and 13C-NMR, which together can distinguish the isomeric hexitols, to further analyze the ethanol-soluble fraction.
74] Chewing gum also increases secretion of saliva and pancreatic juices, and a recent study proposed that sorbitol and hexitol found in sugar-free gum may also play a role in the reduction of postoperative ileus.