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Lactones 31. Synthetic odoriferous unsaturated γ-lactones

✍ Scribed by Robert Obara; Antoni Szumny; Alicja Wzorek; Maia Szmigiel-Pieczewska; Agata Białońska; Zbigniew Ciunik; Czesław Wawrzeńczyk

Book ID
102203593
Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
280 KB
Volume
23
Category
Article
ISSN
0882-5734

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✦ Synopsis

Abstract

Starting from γ, __δ‐unsaturated terpenoid acids, the corresponding δ‐iodo‐γ‐__lactones and __γ‐iodo‐δ‐__lactones were obtained. Dehydrohalogenation of __δ‐iodo‐γ‐__lactones with DBU gave unsaturated __γ‐__lactones with an exocyclic or alkyl chain double bond. Both types of double bonds possessed the E configuration. The composition of product mixture of dehydrohalogenation strongly depended on the conditions (solvent, temperature) of the process. Odour evaluation of the lactones obtained showed that lactones with two double bonds in the molecule (
11 and
12) possess intensive, well‐marked, fresh mushroom odours. Lactones with one double bond and one methyl group at C‐4 (
5a,
6a,
6b and
5d,
6d,
6e) are characterized, in general, by milky, coconut and creamy odours with different notes. Lactones with two methyl groups at C‐4 possess herbal (
5c,
5f) or woody (
6c) odours. Copyright © 2008 John Wiley & Sons, Ltd.

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