Formation of Hydrazones and Osazones

  • Another property of the hexoses which is due to the presence of an aldehyde group in the molecule, is that of forming addition products with phenyl hydrazine, known as "hydrazones" and "osazones." For example, glucose reacts with phenyl hydrazine in acetic acid solution, in two stages.

    The hydrazones of the common sugars, with the exception of the one from mannose, are colorless compounds, easily soluble in water. Hence, they do not serve for the separation or identification of the individual sugars. But if the solution in which they are formed contains an excess of phenyl hydrazine and is heated to the temperature of boiling water for some time, the alcoholic group next to the aldehyde group (the terminal alcohol group in ketoses) is first oxidized to an aldehyde and then a second molecule of phenyl hydrazine is added on, as illustrated above, forming a di-addition-product, known as an "osazone." The osazones are generally more or less soluble in hot water, but on cooling they crystallize out in yellow crystalline masses each with definite melting point and crystalline form. All sugars which have active aldehyde groups in the molecule form osazones. These afford excellent means of identification of unknown sugars, or of distinguishing between sugars of different origin and type.