Osazone

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Template:Short description

File:D-glucose-osazone-3D-balls.png
Ball-and-stick model of glucosazone

Osazone are a class of carbohydrate derivatives found in organic chemistry formed when reducing sugars are reacted with excess of phenylhydrazine at boiling temperatures.[1][2]

Formation

Osazone formation was developed by Emil Fischer,[3] who used the reaction as a test to identify monosaccharides.

The formation of a pair of hydrazone functionalities involves both oxidation and condensation reactions.[4] Since the reaction requires a free carbonyl group, only "reducing sugars" participate. Sucrose, which is nonreducing, does not form an osazone.

File:Osazone-Formation.png
A typical reaction showing the formation of an osazone. D-glucose reacts with phenylhydrazine to give glucosazone. The same product is obtained from fructose and mannose.
File:Osazone.svg
General steps in osazone formation

Appearance

Osazones are highly coloured and crystalline compounds. Osazones are readily distinguished.[5]

  • Maltosazone (from maltose) forms petal-shaped crystals.
  • Lactosazone (from lactose) forms powder puff-shaped crystals.
  • Galactosazone (from galactose) forms rhombic-plate shaped crystals.
  • Glucosazone (from glucose, fructose or mannose) forms broomstick or needle-shaped crystals.

Historic references

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References

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