Phenylglyoxal

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

• References

• 1 von Pechmann H. Chem. Ber. 1887; 20: 2904
• 2 Mikol GJ, Russell GA. Org. Synth. Coll. Vol. V. Wiley & Sons; New York: 1973
• 3 Riley HA, Gray AR. Org. Synth. Coll. Vol. II. Wiley & Sons; New York: 1943
• 4 Takahashi K. J. Biol. Chem. 1968; 243: 6171
• 5 Eftekhari-Sis B, Zirak M, Akbari A, Hashemi MM. J. Heterocycl. Chem. 2010; 47: 463
• 6 Eftekhari-Sis B, Akbari A, Amirabedi M. Chem. Heterocycl. Compd. 2011; 46: 1330
• 7 Rimaz M, Khalafy J. ARKIVOC 2010; (ii): 110
• 8 Husain A, Drabu S, Kumar N. Acta Pol. Pharm. 2009; 66: 243
• 9 Ayaz M, Dietrich J, Hulme C. Tetrahedron Lett. 2011; 52: 4821
• 10 Quiroga J, Acosta PA, Cruz S, Abonia R, Insuasty B, Nogueras M, Cobo J. Tetrahedron Lett. 2010; 51: 5443
• 11 Yang M.-L, Kuo P.-C, Damu AG, Chang R.-J, Chiou W.-F, Wu T.-S. Tetrahedron 2006; 62: 10900
• 12 Ishihara K, Yano T, Fushimi M. J. Fluorine Chem. 2008; 129: 994