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Essential‐oil inspired synthetic libraries: synthesis, spectral and gas‐chromatographic properties of new fenchyl esters
Author(s) -
Blagojević Polina D.,
Pešić Marko S.,
Radulović Niko S.
Publication year - 2017
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3380
Subject(s) - chemistry , chemical shift , proton nmr , organic chemistry , combinatorial chemistry , computational chemistry
Herein, the design, synthesis, and gas‐chromatographic and spectral characterization of a library of endo ‐ and exo ‐fenchyl esters (formate, acetate, propanoate, butanoate, isobutanoate, pentanoate, isopentanoate, 2‐methylbutanoate, hexanoate, heptanoate, octanoate, nonanoate, tiglate, angelate, senecioate and benzoate; 32 compounds in total) were described. 1D‐ and 2D–NMR experiments combined with 1 H iterative full spin analysis and GIAO (gauge invariant atomic orbitals) computation of NMR chemical shifts and coupling constants for DFT‐calculated minimum energy conformations enabled a complete 1 H–NMR assignment of the higher‐order signals of the fenchyl‐core protons. Library members, derivatives of a well‐known monoterpenol of economical importance, often encountered in essential oils (EOs), might potentially represent new (up to now undiscovered), or be classified as rare, natural products. The data summarized in this work should facilitate future EO analyses, especially those studies dealing with minor constituents. The benefits of the usage of (untargeted) metabolome‐inspired synthetic libraries in the analysis of EOs were discussed.