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The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis

MPS-Authors
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Ouyang,  Jie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Dao,  Quang Minh
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Dehn,  Stefanie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lingnau,  Julia B.
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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De,  Chandra Kanta
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Ouyang, J., Bae, H., Jordi, S., Dao, Q. M., Dossenbach, S., Dehn, S., et al. (2021). The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis. Angewandte Chemie International Edition, 60(11), 5666-5672. doi:10.1002/anie.202014609.


Cite as: http://hdl.handle.net/21.11116/0000-0008-1DBB-6
Abstract
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.