Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism |
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Authors: | Yaguchi Yoshihiro Nakahashi Atsufumi Miura Nobuaki Sugimoto Daisuke Monde Kenji Emura Makoto |
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Affiliation: | Corporate Research and Development Division, Takasago International Corporation, 4-11, 1-Chome, Nishi-yawata, Hiratsuka city, Kanagawa 254-0073, Japan. |
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Abstract: | 2-Substituted-3(2H)-furanone derivatives are industrially significant aroma compounds possessing a unique keto-enol tautomeric feature causing their racemization. Absolute configurations of two flavorous furanones, which have remained unclear for the past 40 years since their discovery, were clarified by the vibrational circular dichroism technique as well as chemical relay reactions. Odor evaluation of each enantiomer revealed relationships between their configurations and their odor activities. |
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