The synthesis of 2-(2-pentenyl) furans and their relationship to the reversion flavor of soybean oil
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- Smagula, M.S., Ho, CT. & Chang, S.S. J Am Oil Chem Soc (1979) 56: 516. doi:10.1007/BF02680192
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cis- andtrans-2-(2-Pentenyl)furans were synthesized and structures were confirmed by infrared, nuclear magnetic resonance and mass spectroscopy. Preliminary organoleptic evaluation of oil solutions of the compounds indicated that thecis isomer had a flavor threshold of ca. 0.25 ppm. with odor and flavor descriptions of beany, grassy and buttery at 0.50 ppm; and that thetrans isomer had a flavor threshold of ca. 0.50 ppm with odor and flavor descriptions of beany, grassy and buttery at 1 ppm and strong painty and metallic at 4 ppm. These compounds, if found in soybean oil through the autoxidation of linolenate, may contribute to the characteristic reversion flavor.