Cereal Chem 38:207 - 220.  |  VIEW ARTICLE

Preparation and Properties of Galactosylisomaltol and Isomaltol.

J. E. Hodge and E. C. Nelson. Copyright 1961 by the American Association of Cereal Chemists, Inc. 

Isomaltol, an enolic compound (C6H6O[3]), first isolated in trace amounts by Backe in 1910 from a steam distillate of bread, is now prepared from lactose in 25% over-all yield. Dehydration of the glucose moiety of lactose by reaction with secondary amine salt in tertiary amine-buffered alcoholic medium yields the new compound, isomaltol beta-D-galactoside, which is hydrolyzed or pyrolyzed to produce Backe's isomaltol. Reaction of maltose with piperidine acetate under the same conditions yields 1-deoxy-1-piperidino- maltulose. This new Amadori compound does not dehydrate to a glucoside of isomaltol analogous to the lactose reaction. Comparison of the properties of isomaltol with those of maltol under identical conditions shows that isomaltol is not a pyrone but probably a furan derivative. Isomaltol and maltol probably are formed in bread by Maillard-type browning reactions, and not by fermentation, as Backe assumed.