Chemical conversion of alpha-keto acids in relation to flavor formation in fermented foods.
Formation of flavor compounds from branched-chain alpha-keto acids in fermented foods such as cheese is believed to be mainly an enzymatic process, while the conversion of phenyl pyruvic acid, which is derived from phenylalanine, also proceeds chemically. In this research, the chemical conversion of alpha-keto acids to aldehydes with strong flavor characteristics was studied, with the main focus on the conversion of alpha-ketoisocaproic acid to the aldehyde 2-methylpropanal, and a manganese-catalyzed reaction mechanism is proposed for this conversion. The mechanism involves keto-enol tautomerism, enabling molecular oxygen to react with the beta-carbon atom of the alpha-keto acid, resulting in a peroxide. This peroxide can react in several ways, leading to unstable dioxylactone or noncyclic intermediates. These intermediates will break down into an aldehyde and oxalate or carbon oxides (CO and CO(2)). All the alpha-keto acids tested were converted at pH 5.5 and in the presence of manganese, although their conversion rates were rather diverse. This chemical reaction might provide new ways for controlling cheese flavor formation with the aim of acceleration of the ripening process or diversification of the flavor characteristics.
Smit
Bart A
BA
NIZO Food Research, Department of Flavor, Nutrition, and Ingredients, P.O. Box 20, 6710 BA Ede, The Netherlands.
Engels
Wim J M
WJ
Alewijn
Martin
M
Lommerse
Gijs T C A
GT
Kippersluijs
Erwin A H
EA
Wouters
Jan T M
JT
Smit
Gerrit
G
D000447:Aldehydes / Q000737:chemistry; D043302:Cultured Milk Products / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007651:Keto Acids / Q000737:chemistry*; D008345:Manganese / Q000737:chemistry; D013649:Taste
D000447:Aldehydes; D007651:Keto Acids; D008345:Manganese; C013082:alpha-ketoisocaproic acid; C017439:isobutyraldehyde