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Angew Chem Int Ed Engl


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"
Journal Title:Angew Chem Int Ed Engl
Year:2021
Volume:20210209
Issue:11
Page Number:5666 - 5672
DOI: 10.1002/anie.202014609
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"

 
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Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <http://www.pherobase.com>.
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