Norbert G. De Kimpe, Christian V. Stevens, Marian A. Keppens
Sep 1, 1993
Citations
1
Influential Citations
56
Citations
Journal
Journal of Agricultural and Food Chemistry
Abstract
A new straightforward synthesis of 2-acetyl-1-pyrroline, the principal rice flavor component with a cracker-like flavor, is reported. The reaction sequence involves the conversion of pyrrolidine into tripyrroline, subsequent hydrocyanation of the latter into 2-cyanopyrrolidine, oxidation into 2-cyano-1-pyrroline, and Grignard addition of methylmagnesium iodide, affording an overall yield of 16-19% from pyrrolidine. In similar way, 2-propionyl-1-pyrroline, a recently discovered flavor component of popcorn, was prepared in addition to several higher analogues, i.e., 2-acyl-1-pyrrolines. Also, the synthesis of 2-(acetyl-d 3 )-1-pyrroline, a deuterated derivative of the rice flavor compound which is useful for the stable isotope dilution assay, is described