A Chemical Study of Burley Tobacco Flavour (Nicotiana tabacum L.). III. Structure Determination and Synthesis of 5-(4-Methyl-2-furyl)-6-methylheptan-2-one (“Solanofuran”) and of 3,4,7-Trimethyl-1,6- dioxa-spiro[4.5]dec-3-en-2-one (“Spiroxabovolide”), Two New Flavour Components of Burley Tobacco
✍ Scribed by E. Demole; Mrs C. Demole; D. Berthet
- Publisher
- John Wiley and Sons
- Year
- 1973
- Tongue
- German
- Weight
- 396 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Two novel constituents of Burley tobacco condensate were shown to be 5‐(4‐methyl‐2‐furyl)‐6‐methylheptan‐2‐one (solanofuran, 4) and 3,4,7‐trimethyl‐1,6‐dioxa‐spiro[4.5]‐dec‐3‐en‐2‐one (spiroxabovolide, 6). These structures were deduced from spectral data and confirmed by synthesis.
Solanofuran (4) was prepared via the dye‐sensitized photo‐oxygenation of solanone (1). This type of reaction involving the uncommon ‘diene‐addition’ of ^1^O~2~ to a conjugated acyclic diene system was thus applied for the first time to the synthesis of a terpenoid furan, a route that might have some biogenetic significance.
Both solanofuran (4) and spiroxabovolide (6) display interesting organoleptic properties. Identification of these compounds increases to 210 the total number of Burley tobacco flavour constituents so far characterized in this laboratory.