The Dreywood Anthrone Reaction as Affected by Carbohydrate Structure

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Abstract
Anthrone in sulfuric acid is a general reagent for carbohydrates. However, the phenylosa-zones of glucose and galactose and the phenylosotriazole of glucose do not give this test, whereas mannose phenylhydraz-one gives a positive reaction. These facts are connected with the structure of these compounds. The osazones and osotria-zoles differ from the other compounds by yielding osones with strong acids, while the hydrazones are reconverted to the original sugars. Their chemical transformations are substantiated by the anthrone reaction. The anthrone reaction seems to need the presence of a furfural structure. It is thought that melanoidins may be produced in 2 ways. The 1st is through formation of 3-C fragments which polymerize and react with amino acid. The 2d way requires higher temps. and, under these conditions, hydroxymethylfurfural is formed, which then yields melanoidins by reacting with amino acid.

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