| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345400 | Tetrahedron: Asymmetry | 2015 | 7 Pages |
Abstract
The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(−)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The racemate (±)-1 made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(2E,4R,5R)-trans-4,5-Epoxy-(E)-2-decenalC10H16O2ee 97.2% (chiral GC)[α]D24 = +26.2 (c 2.24, hexane)Source of chirality: Sharpless asymmetric epoxidation [(−)-DET]Absolute configuration: (4R,5R)
Related Topics
Physical Sciences and Engineering
Chemistry
Inorganic Chemistry
Authors
Kenji Mori, Kazumi Osada, Masayasu Amaike,