Synthesis and Sensory Studies of Umami-Active Scaffolds

• Published in: Chemistry & biodiversity Vol. 11; no. 11; pp. 1782 - 1797
• Main Authors: Backes, Michael, Paetz, Susanne, Vössing, Tobias, Ley, Jakob Peter
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01.11.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Amides - chemical synthesis; Amides - chemistry; Bridged Bicyclo Compounds - chemical synthesis; Bridged Bicyclo Compounds - chemistry; Carboxamides; Fractional crystallization; Menthol - chemistry; Molecular Conformation; Sensory evaluation; Taste; Umami; Fractional crystallization; Umami; Sensory evaluation; Carboxamides
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201400113

The class of 2‐isopropyl‐5‐methylbicyclo[4.1.0]heptane‐7‐carboxamides, 1–4, has been identified as potent umami‐tasting molecules. A scalable synthesis of this challenging scaffold and new sensory insights will be presented. Interestingly, the umami characteristics differ remarkably, depending on constitutional and stereochemical features of the parent scaffold. During our studies, we could identify the carboxamide moiety as a crucial factor to influence the umami intensity of these scaffolds. In addition, the configuration of the cyclopropyl moiety exerts some influence, whereas the absolute configuration of the menthyl scaffold, at least the tested D‐ and L‐configuration, is less important.