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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
Author(s) -
Demole E.,
Demole C.,
Berthet D.
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560116
Subject(s) - chemistry , nicotiana tabacum , organoleptic , flavour , conjugated system , furan , stereochemistry , conjugated diene , terpenoid , organic chemistry , polymer , food science , monomer , biochemistry , gene
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.