Dedicated to my parents and my research supervisor Dr. Bagher Eftekhari-Sis.
Introduction
Phenylglyoxal is a yellow liquid that polymerized on standing which stored as monohydrate
form (PhCOCHO·H2O), a white crystalline solid with a melting point of 77 °C. It can be prepared via
different procedures,[1]
[2] but the most popular method for synthesis of phenylglyoxal is the oxidation of acetophenone
with selenium dioxide[
3
] (Scheme [1]). Because phenylglyoxal contains both an aldehyde and ketone functional group it
is useful in both organic and biological chemistry. As a versatile reagent, it has
been used extensively in synthesizing a broad range of N-heterocyclic compounds with
biological and pharmaceutical activities. The aldehyde and ketone functional group
of phenylglyoxal can be converted into other useful groups such as hydroxyl, carboxylic
acid and ester which are more attractive groups in organic synthetic chemistry. Phenylglyoxal
has also many indispensible roles in biological chemistry. As a reagent, it is useful
for the chemical modification of arginine residues in proteins. It reacts with the
guanidino group of the arginine residue under mild conditions.[
4
]
Scheme 1 Preparation of phenylglyoxal monohydrate
