Antimicrobial Properties of α-Dicarbonyl and Related Compounds

Abstract

By surface plating on plate count agar, 0.005 M (430 ppm) of the α-dicarbonyl compound, diacetyl, inhibited 28 of 40 organisms with the medium at pH 6 but only 11 at pH 8. Diacetyl was more effective against gram-negative bacteria and yeasts than non-lactic gram-positive bacteria and least effective against lactic acid bacteria. Acetoin, butanedioldiacetate and five butanediol isomers were considerably less effective than diacetyl, although all were more effective at pH 6 than 8. Diacetylmonoxime and diacetyldioxime were more effective than the diols and were less affected by pH of medium than diacetyl. Phenylglyoxal (PG) and 1,2-cyclohexanedione (CHD) ranked closest to diacetyl but, unlike the latter, they were more effective against gram-positive bacteria and less so against fungi and gram-negative bacteria. All 12 compounds were more effective against selected organisms by pour plating and in broth culture than by surface plating. Like diacetyl, CHD and PG are α, α-dicarbonyls and are widely used as arginine reactive agents resulting in the blockage of enzyme-substrate reactions. Although their antimicrobial activity may be due to this property, they apparently affect different enzymes than diacetyl because their antimicrobial spectra were different. The possibility of a class of food-use antimicrobial agents bearing α-dicarbonyl groups is suggested by the findings of this study.