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  The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis

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.

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 Creators:
Ouyang, Jie1, Author              
Bae, Hanyong2, Author
Jordi, Samuel3, Author
Dao, Quang Minh4, Author              
Dossenbach, Sandro3, Author
Dehn, Stefanie1, Author              
Lingnau, Julia B.5, Author              
De, Chandra Kanta1, Author              
Kraft, Philip3, Author
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Department of Chemistry, Sungkyunkwan University, 2066, Seobu-ro, Jangan-gu, Suwon, 16419 Republic of Korea, ou_persistent22              
3Givaudan Schweiz AG, Fragrances S&T, Ingredients Research, Kemptpark 50, 8310 Kemptthal, Switzerland, ou_persistent22              
4Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
5Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: 2-epi-ziza-6(13)en-3-one; asymmetric Mukaiyama-Michael addition; enantioselective synthesis; smelling principle; vetiver oil
 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.

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Language(s): eng - English
 Dates: 2020-11-012020-12-102020-12-142021-03-08
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202014609
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (11) Sequence Number: - Start / End Page: 5666 - 5672 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851