Conformational Flexibility Of Musks

Lead Research Organisation: King's College London
Department Name: Chemistry

Abstract

Musk odorants represent a class of fragrances which exhibit a warm, sensual, animalistic and natural scent, and were introduced into the perfume industry at the beginning of 20th century. Structurally, musk odorants are remarkably diverse, including macrocyclic molecules, polycyclic benzene derivatives, nitro arenes, and linear aliphatic compounds, and therefore there is lack of knowledge of the molecular determinants that lead to musk odour. Moreover, some classes of musks such as nitro musks have been proved to be toxic, while other such as polycyclic musks resulted in bioaccumulation and biomagnification through the food chain. Macrocyclic musks, which are biodegradable and exhibit strong olfactory and fixative properties, have an expensive and complex synthesis. There is interest in the perfume industry to develop new musks, but these molecules are conformationally rich and there is very limited knowledge of their active conformations. This project aims to study the conformations of prototypical musks and gain an understanding of the interactions that determine them. This is essential for understanding odorant identification and, more broadly, for rational design and development of new odorants. To achieve our goals, we will use a cutting-edge structural technique, broadband rotational spectroscopy, which allows unambiguous identification of the different conformations present in a sample, in combination with molecular modelling.

Publications

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Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/N509498/1 30/09/2016 29/09/2021
1976229 Studentship EP/N509498/1 30/09/2017 30/11/2021 Ecaterina Burevschi
EP/R513064/1 30/09/2018 29/09/2023
1976229 Studentship EP/R513064/1 30/09/2017 30/11/2021 Ecaterina Burevschi
 
Description Musk odorants are known for their warm, sensual, animalistic and natural scent. Structurally, musk odorants are very diverse, including macrocyclic molecules, polycyclic benzene derivatives, nitro arenes, and linear aliphatic compounds, and therefore there is lack of knowledge of the molecular determinants that lead to musk odour. Moreover, some classes of musks such as nitro and polycyclic musks have been proved toxic and non-biodegradable and hence removed form the fragrance industry. Macrocyclic musks, which are biodegradable and exhibit strong olfactory and fixative properties, have an expensive and complex synthesis. There is interest in the perfume industry to develop new musks, but these molecules are conformationally rich and there is very limited knowledge of their active conformations. My project is focused on studying the conformational landscape of musks belonging to different classes and understanding of the interactions that determine them. To achieve our goals, we are using a cutting-edge structural technique, broadband rotational spectroscopy, which allows unambiguous identification of the different conformations present in a sample, in combination with molecular modelling. So far a few musk odorants belonging to the acyclic and macrocyclic classes have been characterised. The analysis of the results is on-going, however the outcome looks promising.
Exploitation Route The outcome of this project will be relevant to perfume industry, where there is an interest in understanding the structure-odor relationship in musk odorants. It will be useful for rational design and development of new odorants.
Sectors Chemicals,Other

 
Description Accurate spectroscopic characterization and benchmarking study of styrene-water 
Organisation Chongqing University
Country China 
Sector Academic/University 
PI Contribution This collaboration involves looking at complexes of styrene with water in gas phase using two complementary techniques.
Collaborator Contribution This collaboration involves looking at complexes of styrene with water in gas phase using two complementary techniques. The group in Chongqing University have initiated the project, contributing with experimental and theoretical work. The group in Shanghai University has performed theoretical analysis.
Impact This collaboration has been a success, the results will be submitted for a publication.
Start Year 2018
 
Description Accurate spectroscopic characterization and benchmarking study of styrene-water 
Organisation Shanghai University
Country China 
Sector Academic/University 
PI Contribution This collaboration involves looking at complexes of styrene with water in gas phase using two complementary techniques.
Collaborator Contribution This collaboration involves looking at complexes of styrene with water in gas phase using two complementary techniques. The group in Chongqing University have initiated the project, contributing with experimental and theoretical work. The group in Shanghai University has performed theoretical analysis.
Impact This collaboration has been a success, the results will be submitted for a publication.
Start Year 2018
 
Description Complexes of fenchone with water by rotational spectroscopy 
Organisation University of Lille
Country France 
Sector Academic/University 
PI Contribution In this collaboration we looking at complexes of fenchone with water in gas phase using MW spectroscopy, where two complementary techniques are used.
Collaborator Contribution Our collaborators have contributed with experimental and theoretical data.
Impact The work on this collaboration is ongoing. So far we have successful outcomes, which will be submitted for a publication.
Start Year 2018
 
Description Firmenich 
Organisation Firmenich
Country Switzerland 
Sector Private 
PI Contribution I have benefitted from the industrial perspective and from presenting my research to a wider audience that includes analytical and synthetic industrial chemists.
Collaborator Contribution Firmenich is a private company in the fragrance and flavour industry. They have synthesised and patented two of the musk compounds I am studying in my PhD project. These compounds are widely used in the perfume industry. Firmenich supplied all the compounds we have investigated, with high purity, and had provided advice throughout the analysis. Our group and Firmenich share an interest in musk odorants, specifically how their structures relate to the musk scent.
Impact The outcomes of this collaboration will be published.
Start Year 2017
 
Description James Allen's Girls' School Outreach Talk 
Form Of Engagement Activity A talk or presentation
Part Of Official Scheme? No
Geographic Reach Regional
Primary Audience Schools
Results and Impact Around 30 girls, aged 15-18 years, attended the talk, where I have presented briefly my project and my experience as a PhD student. I have also spoken about my university degree and university life in general. Additionally, we discussed about possible career paths in science, which seemed a topic of interest for the audience. The talk was followed by interesting questions and discussions. Feedback from the school organiser showed that my talk was very well received and inspired some of the Year 12's students to consider Chemistry and King's for university (they attended an Explore King's event on 28 Nov 2018).
Year(s) Of Engagement Activity 2018