Cereal Chem 52:166 - 172.  |  VIEW ARTICLE
Studies on the Mechanism of Color Formation in Glucose Syrups.

S. Ramchander and M. S. Feather. Copyright 1975 by the American Association of Cereal Chemists, Inc. 

Two furans, 5-(hydroxymethyl)-2-furaldehyde (HMF) and 2-(2-hydroxyacetyl)-furan (HAF), were identified among the products produced during the heat-decomposition and coloring of a glucose syrup. The yields of both compounds increased with the rate of color formation in the syrup. The mechanism by which these furans are produced (that is, via a nitrogenous Amadori product or via an acid-catalyzed dehydration, both without fission of the carbon chain) was studied by producing HMF and HAF from a syrup which was adjusted to pH 2.5 and which contained D-glucose-2-H3. It is known that when D-glucose-2-H3 is converted to HMF and HAF via amine condensation and the Amadori rearrangement, radiochemically inert furans are formed; whereas in an acid-catalyzed dehydration reaction of the unsubstituted sugar, the resulting HMF is tritium labeled on the aldehyde carbon and HAF on the hydroxymethyl carbon. The resulting HMF and HAF produced in the syrup were essentially radiochemically inert, thus indicating that these compounds were not produced via an acid-catalyzed non-nitrogenous reaction. They are most likely produced via an Amadori compound in Maillard-type reactions.