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Effect of Fluorination on Skin Sensitization Potential and Fragrant Properties of Cinnamyl Compounds
Author(s) -
Charpentier Julie,
Emter Roger,
Koch Heinz,
Lelièvre Dominique,
Pannecoucke Xavier,
CouveBonnaire Samuel,
Natsch Andreas,
Bombrun Agnes
Publication year - 2018
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800013
Subject(s) - cinnamyl alcohol , cinnamaldehyde , skin sensitization , chemistry , sensitization , alcohol , in vitro , odor , organic chemistry , ethanol , biochemistry , medicine , immunology , catalysis
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.