Osazone

Ball-and-stick model of glucose osazone

Osazones are a class of carbohydrate

derivatives found in organic chemistry
formed when sugars are reacted with
excess of phenylhydrazine.[1]
The famous German chemist Emil
Fischer[2] developed and used the
reaction to identify sugars whose
stereochemistry differed by only one
chiral carbon.[3][4] Glucosazone and
fructosazone are identical.[5]

Osazones formation test involves the

reaction of a reducing sugar (free
carbonyl group) with excess of
phenylhydrazine when kept at boiling
temperature. All reducing sugars form
osazones. Therefore, sucrose, for
example, does not form osazone crystals
because it is a non reducing sugar as it
has no free carbonyl group.
The reaction involves formation of a pair
of phenylhydrazone functionalities,
concomitant with the oxidation of the
hydroxymethyl group in alpha carbon
(carbon atom adjacent to the carbonyl
center).

The reaction can be used to identify

monosaccharides. It involves two
reactions. Firstly glucose with
phenylhydrazine gives
glucosephenylhydrazone by elimination
of a water molecule from the functional
group. The next step involves reaction of
one equivalent of
glucosephenylhydrazone with two
equivalents of phenylhydrazine (excess).
First phenylhydrazine is involved in
oxidizing the alpha carbon to a carbonyl
group, and the second phenylhydrazine
involves in removal of one water
molecule with the new-formed carbonyl
group of that oxidized carbon and
forming the similar carbon nitrogen
bond.[6] The alpha carbon is attacked
here because it is more reactive than the
others.

Osazones are highly coloured and

crystalline compounds and can be easily
detected. Each sugar has a characteristic
crystal form of osazones.

Maltose forms petal-shaped crystals.

 Lactose forms powder puff-shaped
crystals.
Galactose forms rhombic-plate shaped
crystals.
Glucose, fructose and mannose form
broomstick or needle-shaped crystals.

A general reaction showing the formation of an

osazone. D-glucose reacts with phenylhydrazine to
give glucose osazone. The same product is obtained
from mannose.

References
1. Mester, L.; El Khadem, H.; Horton, D.
(1970). "Structure of saccharide
osazones". Journal of the Chemical
Society C: Organic (18): 2567.
doi:10.1039/J39700002567 .
2. Helferich, B. (1953). "Emil Fischer
zum 100. Geburtstag". Angewandte
Chemie. 65 (2): 45.
doi:10.1002/ange.19530650202 .
3. Fischer, Emil (1908). "Schmelzpunkt
des Phenylhydrazins und einiger
Osazone". Berichte der deutschen
chemischen Gesellschaft. 41: 73.
doi:10.1002/cber.19080410120 .
4. Fischer, Emil (1894). "Ueber einige
Osazone und Hydrazone der
 Zuckergruppe". Berichte der
deutschen chemischen Gesellschaft.
27 (2): 2486.
doi:10.1002/cber.189402702249 .
5. Ramakrishnan, S. (2004). Textbook
of Medical Biochemistry . Orient
Blackswan. ISBN 9788125020714.
6. Barry, VINCENT C.; Mitchell, PW
(1955). "Mechanism of Osazone
Formation". Nature. 175 (4448): 220.
Bibcode:1955Natur.175..220B .
doi:10.1038/175220a0 .
PMID 13235861 .

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