| Title: | "The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis" |
| Author(s): | Ouyang J; Bae H; Jordi S; Dao QM; Dossenbach S; Dehn S; Lingnau JB; Kanta De C; Kraft P; List B; |
| Address: | "Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mulheim an der Ruhr, Germany. Department of Chemistry, Sungkyunkwan University, 2066, Seobu-ro, Jangan-gu, Suwon, 16419, Republic of Korea. Givaudan Schweiz AG, Fragrances S&T, Ingredients Research, Kemptpark 50, 8310, Kemptthal, Switzerland" |
| ISSN/ISBN: | 1521-3773 (Electronic) 1433-7851 (Print) 1433-7851 (Linking) |
| 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" |
| Keywords: | 2-epi-ziza-6(13)en-3-one asymmetric Mukaiyama-Michael addition enantioselective synthesis smelling principle vetiver oil; |
| Notes: | "PubMed-not-MEDLINEOuyang, Jie Bae, Hanyong Jordi, Samuel Dao, Quang Minh Dossenbach, Sandro Dehn, Stefanie Lingnau, Julia B Kanta De, Chandra Kraft, Philip List, Benjamin eng Research Support, Non-U.S. Gov't Germany 2020/12/15 Angew Chem Int Ed Engl. 2021 Mar 8; 60(11):5666-5672. doi: 10.1002/anie.202014609. Epub 2021 Feb 9" |
