In:
Flavour and Fragrance Journal, Wiley, Vol. 36, No. 5 ( 2021-09), p. 584-592
Abstract:
In this study, all stereoisomers of cognac lactone ( 1 ) were synthesized with over 99% enantiomeric excess via diastereomeric resolution using N ‐benzyloxycarbonyl‐ l ‐proline ( N ‐Cbz‐ l ‐proline) as a resolving agent. N ‐Cbz‐ l ‐proline could be applied for the diastereomeric resolution of both syn ‐ and anti ‐forms and yielded all diastereomers in over 99% diastereomeric excess. The odour properties of racemic and optically active 1 were evaluated for their orthonasal aromas. All the stereoisomers had different odour characteristics and thresholds. In general, the (3 S )‐ and (3 R )‐forms had fruity and herbal notes, respectively, and (3 R ,4 S )‐ 1 had the lowest odour threshold at 0.01 ppm. All stereoisomers, except (3 R ,4 S )‐ 1 , showed antibacterial activity against Staphylococcus aureus . Moreover, (3 S ,4 S )‐ 1 showed high antibacterial activity against both S aureus and Escherichia coli .
Type of Medium:
Online Resource
ISSN:
0882-5734
,
1099-1026
Language:
English
Publisher:
Wiley
Publication Date:
2021
detail.hit.zdb_id:
1483463-7
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