Effects of Sulfur Dioxide on Food Quality - Food Shelf Life Stability: Chemical, Biochemical, and Microbiological Changes - page 272

Hodge in 1953. 45 The reaction is initiated by the formation of a glycosylamine which
undergoes an irreversible rearrangement to a ketoseamine shown below for the
reaction of glucose with an amino acid:

At the pH of most foods, the 1,2-enolamine precursor of the ketoseamine decom-
poses to give a key

-dicarbonyl nitrogen-free intermediate, 3-deoxyhexosulose
(DH), 46,47 which is present in a variety of cyclic and acyclic isomeric forms; essen-
tially, this molecule consists of glucose with one molecule of water removed and
for this reason the term “amine-assisted dehydration” has been coined for the overall
process of the conversion of glucose to DH. 48 This, in turn, dehydrates to cis - and
trans -3,4-dideoxyhexosulos-3-ene (DDH) which are by far the most reactive known
intermediates in browning. 49,50 The structures of these important intermediates in
browning are as follows:

α

DDH is converted to other intermediates in the route to color. It behaves as an
α -dicarbonyl compound in the Strecker degradation of amino acids while a proportion