Effect of Fluorination on Skin Sensitization Potential and Fragrant Properties of Cinnamyl Compounds

  • Chem Biodivers. 2018 Apr;15(4):e1800013. doi: 10.1002/cbdv.201800013.
Julie Charpentier  1 ,  Roger Emter  1 ,  Heinz Koch  1 ,  Dominique Lelièvre  1 ,  Xavier Pannecoucke  2 ,  Samuel Couve-Bonnaire  2 ,  Andreas Natsch  1 ,  Agnes Bombrun  1
Affiliations
  • 1. Ingredients Research, Givaudan International SA, Überlandstrasse 138, 8600, Dübendorf, Switzerland.
  • 2. Normandie Université, COBRA, UMR 6014 et FR 3038, Université Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821, Mont Saint-Aignan Cedex, France.
PMID: 29476591 DOI: 10.1002/cbdv.201800013
Abstract

A series of three α- and three β-fluorinated representatives of the family of cinnamate-derived odorants (cinnamaldehyde (1), cinnamyl alcohol (2), and ethyl cinnamate (3)) as used as fragrance ingredients is described. Olfactive evaluation shows that the fluorinated compounds exhibit a similar odor profile to their parent compounds, but the olfactive detection thresholds are clearly higher. In vitro evaluation of the skin sensitizing properties with three different assays indicates that α-fluorination of Michael acceptor systems 1 and 3 slightly improves the skin sensitization profile. α-Fluorocinnamyl alcohol 2b is a weaker skin sensitizer than cinnamyl alcohol 2a by in vitro tests and the fluorinated product drops below the sensitization threshold of the KeratinoSens® assay. On the Other hand, β-fluorination of compounds 1 - 3 results in highly reactive products which display a worsened in vitro skin sensitization profile.

Keywords
KeratinoSens ®; cinnamyl derivatives; fluoroalkenes; fragrance ingredients; skin sensitization.
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