Stereoselective synthesis of (6Z,8E)-undeca-6,8,10-trien-3-one (yuzunone) for its characterization in yuzu and various citrus essential oils.

(6Z,8E)-Undeca-6,8,10-trien-3-one (yuzunone) is reported to be one of the main olfactory contributors of the specific fruity-green-balsamic odor of yuzu peel oil. Using an original stereoselective synthesis, we prepared a pure sample of yuzunone, which was used as a reference compound to check its presence by GC-MS and GC-O in 5 commercial samples of yuzu and citrus essential oils. Surprisingly, we could not detect yuzunone by GC-MS in any of our samples. However, it could be detected by a small part of the panelists involved in GC-O/AEDA experiments in a yuzu commercial oil, but its olfactory contribution proved to be very limited.