Quantitative model studies on the formation of aroma-active aldehydes and acids by strecker-type reactions.
Application of aroma extract dilution analysis on the volatiles formed by reacting glucose and L-phenylalanine (30 min, 100 degrees C) revealed the Strecker aldehyde, phenylacetaldehyde (PA), and, in addition, phenylacetic acid (PAA) as the two key odorants among the volatiles formed. Quantitative measurements on alpha-dicarbonyl formation revealed that the 3-deoxyosone and glyoxal were formed as the first prominent sugar degradation products, whereas 2-oxopropanal became predominant after approximately 4 h at 100 degrees C. Among the four alpha-dicarbonyls analyzed, 2-oxopropanal proved to be the most effective in generating PA as well as PAA from phenylalanine, but the reaction parameters significantly influenced the ratio of both odorants; for example, at pH 3.0 the ratio of PA to PAA was 3:1, whereas at pH 9.0 the ratio was 1:5. Furthermore, in the presence of oxygen and copper ions the formation of the acid was further increased. 3-Deoxyosone and glucosone were found to be effective precursors of phenylacetaldehyde, but neither was very effective in acid generation. On the basis of the results, a new oxygen-dependent formation pathway of the Strecker reaction is proposed.
Hofmann
T
T
Deutsche Forschungsanstalt für Lebensmittelchemie, Lichtenbergstrasse 4, D-85748 Garching, Germany.
Münch
P
P
Schieberle
P
P
D000079:Acetaldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D008956:Models, Chemical; D009812:Odorants; D010648:Phenylacetates / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry
D000143:Acids; D000447:Aldehydes; D002241:Carbohydrates; D010648:Phenylacetates; D010649:Phenylalanine; C032251:isovalerylaldehyde; C025136:phenylacetic acid; D000079:Acetaldehyde; D005947:Glucose; C013192:phenylacetaldehyde