Premium
Synthesis, odour characteristics and antibacterial activities of the stereoisomeric forms of whisky lactone and its thiono analogues
Author(s) -
Shimotori Yasutaka,
Hoshi Masayuki,
Okabe Hayato,
Miyakoshi Tetsuo,
Kanamoto Taisei,
Nakashima Hideki
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.3341
Subject(s) - chemistry , lactone , enantiomer , stereochemistry , organic chemistry
Four stereoisomers of whisky lactone were selectively synthesized in over 99% enantiomeric excess using an amino acid derivative as a resolving agent. Cbz‐L‐proline was the most effective resolving agent, and both trans ‐ and cis ‐stereoisomers were comparatively easily separated. Odour characteristics of whisky thionolactone were different among four stereomeric isomers, and only (3 S ,4 R )‐whisky thionolactone had mushroom and cis ‐jasmone like note. Among all isomers, only (3 R ,4 S )‐whisky lactone showed antibacterial activities against Staphylococcus aureus . Whisky thionolactone had higher activities than whisky lactone, and (3 R ,4 S )‐whisky thionolactone showed the strongest activities of all tested samples. Copyright © 2016 John Wiley & Sons, Ltd.