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Megastigma‐5,8‐dien‐4‐on, ein Aromastoff der gelben Passionsfrucht und des Virginia ‐Tabaks
Author(s) -
Demole Edouard,
Enggist Paul,
Winter Max,
Furrer Anton,
SchulteElte Karl H.,
Egger Bernard,
Ohloff Günther
Publication year - 1979
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.19790620111
Subject(s) - chemistry , passion fruit , aroma , flavor , dehydration , stereochemistry , alcohol , organic chemistry , food science , biochemistry
Megastigma‐5,8‐dien‐4‐one, an aroma constituent of the yellow passion fruit and Virginia tobacco Preparative gas chromatography allowed isolation of megastigma‐5, 8 ( E )‐dien‐4‐one ( 3 ) from small subfractions of both yellow passion fruit and Virginia tobacco condensates. Along with 3 , the Z‐isomer 4 occurs in the aroma of the yellow passion fruit. Both these novel flavor compounds were synthesized by a two‐step, non‐biomimetic route starting from 2, 6, 6‐trimethylcyclohex‐2‐en‐1‐one. The E ‐isomer 3 was also formed by acid‐catalyzed dehydration/rearrangements of ionol‐ and damascol monoepoxides 5, 6, 7, 8 and hydroxy‐ionols and ‐damascol 9, 10 and 11 . Such a biomimetic conversion indirectly supports the assumption that 3 and 4 might originate from the oxidative degradation of carotenoid precursors possibly related to canthaxanthine.