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Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

1996; American Chemical Society; Volume: 44; Issue: 6 Linguagem: Inglês

10.1021/jf950728c

1520-5118

Norbert De Kimpe, Marian Keppens,

Food composition and properties

A new synthetic pathway toward the Maillard flavor compounds 6-acyl-1,2,3,4-tetrahydropyridines and 2-acetyl-1-pyrroline is presented. The reaction sequence involves deprotonation of a vicinal diimine and subsequent alkylation with an N,N-diprotected ω-bromoalkylamine, followed by deprotection and intramolecular transimination of the functionalized intermediate. Acidic workup affords the above-mentioned heterocycles, which are principal flavor constituents of bread and cooked rice, respectively. In addition, the synthesis of the more stable diethyl acetal of 2-acetyl-1-pyrroline is described. Keywords: Rice flavor; bread flavor; 2-acetyl-1-pyrroline; 6-acetyl-1,2,3,4-tetrahydropyridine; Maillard