On the Hodge mechanism of the formation of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine from proline and sugars

• Published in: Journal of agricultural and food chemistry Vol. 42; no. 8; pp. 1739 - 1742
• Main Authors: De Kimpe, Norbert G, Dhooge, Willem S, Shi, Youzhong, Keppens, Marian A, Boelens, Mark M
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-08-1994
• Subjects: Biological and medical sciences; Cereal and baking product industries; Food industries; Fundamental and applied biological sciences. Psychology; Carbonyl compounds; Intermediate product; Nitrogen heterocycle; Proline; Maillard reaction; NMR spectrometry; Bread; Pyridine derivatives; Hydrolysis; Aminoaldehyde; Reaction mechanism; Carbohydrate; Aroma; Mass spectrometry
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf00044a031

The so-called Hodge mechanism for the generation of 6-acetyl-1,2,3,4-tetrahydropyridine, a major Maillard flavor compound in processed foods, from proline and 1,2-propanedione most probably does not involve the intermediacy of N-acetonyl-4-aminobutanal. This finding is based on model experiments in which suitably and doubly protected N-acetonyl-4-aminobutanal was hydrolyzed into the parent compound and in which no trace of the flavor compound could be detected.