(Z)-4,7-Octadiensäure-äthylester und (Z)-Buttersäure-3,5-hexadienylester, zwei neue Aromastoffe der roten Passionsfrucht
✍ Scribed by Max Winter; Ferdinand Näf; Anton Furrer; Wilhelm Pickenhagen; Wolfgang Giersch; Alain Meister; Bruno Willhalm; Walter Thommen; Günther Ohloff
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- German
- Weight
- 342 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Ethyl (Z)‐4,7‐Octadienoate and (Z)‐3,5‐Hexadienyl Butyrate, two New Aroma Components of the Purple Passionfruit
The isolation of ethyl (Z)‐4,7‐octadienoate (1) and (Z)‐3,5‐hexadienyl butyrate (2), two new and important aroma constituents of the purple passionfruit (Passiflora edulis SIMS) is reported.
Ester 1 was synthesized by two different routes: (1) via a Wittig reaction between the known 4‐oxobutyrate 4 and 3‐butenylidenephosphorane, and (2) by thermolysis of (Z)‐8‐acetoxy‐4‐octenoate 7 which was readily accessible from (Z,Z)‐1,5‐cyclooctadiene.
Ester 2 was prepared from the known hex‐3‐yn‐5‐en‐1‐ol (8) by a stereoselective (Z)‐reduction of the triple bond to 9, using Rieke's active metallic zinc, followed by esterification.
The organoleptic properties and the taste threshold values of 1 and 2 are given.