Paper number 37 in this series was published as: A. Grudniewska, K. Dancewicz, A. Białońska, Z. Ciunik, B. Gabryś and C. Wawrzeńczyk, Lactones 37. Synthesis of piperitone derived halogenated lactones and their effect on aphid probing, feeding and settling behavior, RSC Advances2011, 1, 498.
Lactones 38: Synthesis and odoriferous properties of p-menthane lactones†
Version of Record online: 27 MAR 2012
Copyright © 2012 John Wiley & Sons, Ltd.
Flavour and Fragrance Journal
Volume 27, Issue 3, pages 237–243, May 2012
How to Cite
Dams, I., Białońska, A., Ciunik, Z. and Wawrzeńczyk, C. (2012), Lactones 38: Synthesis and odoriferous properties of p-menthane lactones. Flavour Fragr. J., 27: 237–243. doi: 10.1002/ffj.3085
- Issue online: 19 APR 2012
- Version of Record online: 27 MAR 2012
- Manuscript Accepted: 6 DEC 2011
- Manuscript Revised: 10 NOV 2011
- Manuscript Received: 10 JUN 2011
- terpenoid lactones; p-menthanolides; isopulegol; odorous compounds; lactonization
An enantiomeric pair of bicyclic δ-lactones with the p-menthane system was obtained from enantiomerically pure isomers of (1R,2S,5R)-(–) and (1S,2R,5S)-(+)-isopulegol. The Horner–Wadsworth–Emmons olefination of isopulegones followed by hydrolysis of esters and lactonization of acids were the key steps of the syntheses presented. The structures of the compounds were determined by both spectroscopic and crystallographic methods. Enantiomeric p-menthane esters and δ-lactones are characterized by interesting odoriferous properties. Copyright © 2012 John Wiley & Sons, Ltd.