期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 11, 页码 5666-5672出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014609
关键词
2-epi-ziza-6(13)en-3-one; asymmetric Mukaiyama– Michael addition; enantioselective synthesis; smelling principle; vetiver oil
资金
- Max Planck Society
- Deutsche Forschungsgemeinschaft (Leibniz Award)
- European Research Council (Advanced Grant C-H Acids for Organic Synthesis, CHAOS)
- Projekt DEAL
Vetiver oil, produced from the roots of vetiver grass, is a popular perfumery material with a complex mixture of molecules. Its main odorant, (+)-2-epi-ziza-6(13)en-3-one, has a remarkably low odor threshold, giving perfumes a special sensuous aura.
Vetiver oil, produced on a multiton-scale from the roots of vetiver grass, is one of the finest and most popular perfumery materials, appearing in over a third of all fragrances. It is a complex mixture of hundreds of molecules and the specific odorant, responsible for its characteristic suave and sweet transparent, woody-ambery smell, has remained a mystery until today. Herein, we prove by an eleven-step chemical synthesis, employing a novel asymmetric organocatalytic Mukaiyama-Michael addition, that (+)-2-epi-ziza-6(13)en-3-one is the active smelling principle of vetiver oil. Its olfactory evaluation reveals a remarkable odor threshold of 29 picograms per liter air, responsible for the special sensuous aura it lends to perfumes and the quasi-pheromone-like effect it has on perfumers and consumers alike.
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