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- Title
Über die Biosynthese von γ-Dodecanolacton in reifenden Früchten: Aroma-Komponenten der Erdbeere ( Fragaria ananassa) und des Pfirsichs ( Prunus persica).
- Authors
Schöttler, Michael; Boland, Wilhelm
- Abstract
On the Biosynthesis of γ-Dodecanolactone in Ripening Fruits: Flavor Constituents from Strawberries ( Fragaria ananassa) and Peaches ( Prunus persica) Administration of deuterium-labelled 9,10-expoxy[8,8-2H2]heptadecanoic acid 8a/ b and 9,10-dihydroxy-[8,8-2H2]methylheptadecanoate 9 as lower analogues of oleic acid 1 to ripening fruits of strawberries ( Fragaria ananassa) and peaches ( Prunus persica) results in the emission of labelled γ-undecanolactone ( 5) as the lower analog of γ-dodecanolactone ( 2). The transformation proceeds with loss of a single D-atom from C(8) of the precursors. Early precursors, like the C17-epoxy-acids 8a/ b yield (4 R)-γ-undecanolactone ( 5) of high enantiomeric purity, while later intermediates results in (4 R)-γ-undecanolactone ( 5) of low purity. The data support a biosynthetic sequence involving the consecutive action of an epoxide hydrolase and β-oxidation to generate the correct chain length of the lactone percursor. The final steps proceed via cyclization of the 3,4-dihydroxyundecanoic acid 13 to the 3-hydroxy-γ-undecanolactone 14. Elimination of H2O and reduction of the intermediate γ-undec-2-enolactone 15 terminate the biosynthesis of 5. The sequence is representative for the biosynthesis of naturally occurring γ-dodecanolactone ( 2).
- Publication
Helvetica Chimica Acta, 1995, Vol 78, Issue 4, p847
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19950780406