1,4:3,6-Dianhydrohexites

Abstract

It is known that derivatives of isosorbide and isomannide can impart a sweet taste, for example, dimethyl ether of isosorbide is used as an ingredient in the production of chewing gums, hard sweets [1], isosorbide dipropanoate is widely used in the production of bakery products [1]. Mixed isohexite esters and esters (especially isosorbide) are used as flavor enhancers. Currently, isosorbide is proposed to be used as a component of the mixture used for the water-base ink pigment. This component has excellent dispersion stability, which is necessary for printing [1]. All production methods leading to isohexites use the corresponding hexitol as the starting material. To obtain isohexites with a quantitative yield, and in order to avoid adverse reactions, a number of techniques have been developed. The rate of the dehydration sequence in reactions using as the starting compound: 1,4-anhydro derivatives of D-iditol, D-gulitol, D-glucitol, and D-mannitol (from which 1,4:3,6-dianhydro compounds of isoidide (5) and isomannide (4) are obtained) depends on the location of the hydroxyl group (with5 endo as in D-mannitol and D-glucitol, or exo as in D-iditol and D-glucitol). All three isohexites (3-5) were studied by mass spectrometry, especially D-isomannide and their O-deuterated isomers, and 5-nitroisosorbide [1]. The isomannide cation formed as a result of dehydration reactions was also detected in the mass spectra of some isomannide derivatives [1]. Mass spectrometric analysis is used to determine isosorbide and its 5-nitro derivative in human urine and blood plasma.