Stereoisomeric Flavor Compounds LXXXI: Dill Ether and Itscis-Stereoisomers: Synthesis and Enantioselective Analysis

Submerged Cultivation of Pleurotus sapidus with Molasses: Aroma Dilution Analyses by Means of Solid Phase Microextraction and Stir Bar Sorptive Extraction

“…Among the formed reaction products, two peaks were identified as 3,9-epoxy- p -menth-1-ene isomers with identical RI and MS spectra as 37 and 47 in the PSA-IM samples on polar and nonpolar GC columns. Furthermore, dried dill leaves were analyzed by HS-SPME-GC-MS-O, in which only enantiopure (3 S ,3a S ,7a R )-dill ether occurs as its key aroma compound. − This enantiomer was identified in the dill sample by sniffing and MS at the same retention indices on both columns as 37 from PSA-IM. In conclusion, 3,9-epoxy- p -menth-1-ene ( 37 ) identified at RI WAX 1512 and RI DB‑5 1187 in PSA-IM may presumably be attributed to the dill ether (3 S ,3a S ,7a R ) and/or its enantiomer (3 R ,3a R ,7a S ).…”

Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus

“…The trans isomers with an anti-ring connection are considered less favorable from a stereochemical point of view , and are thus not expected to be formed via natural pathways. Among the cis isomers, compounds 1B – 1D are assigned to rather unspecific fruity, herbaceous, flowery, or tarragon-like odor impressions, whereas compound 1A imparts a characteristic dill-like odor. ,− The latter isomer was also identified as a key aroma compound in dill, herein occurring in enantiopure form. , Other natural sources of dill ether isomers are e.g. certain honey varieties. , With respect to potential biosynthetic pathways, an acid-catalyzed degradation of 8-hydroxygeraniol resulting in isomers of compound 1 was demonstrated .…”

“…The chemical syntheses of stereoisomers of compounds 1 and 2 comprise elaborate multistep reactions, and some of these require toxic compounds, such as pyridinium dichromate. ,,,, A biotechnological alternative based on an edible basidiomycete would thus be highly attractive. The objective of this study was to investigate the formation of the isomers of compounds 1 and 2 detected in submerged PSA cultures.…”

Formation of Diastereomeric Dihydromenthofurolactones by Cystostereum murrayi and Aroma Dilution Analysis Based on Dynamic Headspace Extraction

“…33 The odor impressions of the four cis-stereoisomers vary from a characteristic dill-like odor (3a) to rather herbal, flowery, tarragon-like, sweet, and minty odors (3b, 7c, and 7d). 4,34 Natural sources for dill ethers are dill for enantiopure 3a and different honey varieties for all four cis-isomers. 35−37 Based on this occurrence, n-pentane/diethyl ether extracts of these natural sources were used as references for the analysis via MDGC.…”

“…However, the stereoisomers with a trans -connection in the tetrahydrofuran ring system are unlikely to be biosynthesized via natural pathways due to the resulting ring strain . The odor impressions of the four cis -stereoisomers vary from a characteristic dill-like odor ( 3a ) to rather herbal, flowery, tarragon-like, sweet, and minty odors ( 3b , 7c , and 7d ). , Natural sources for dill ethers are dill for enantiopure 3a and different honey varieties for all four cis -isomers. − Based on this occurrence, n -pentane/diethyl ether extracts of these natural sources were used as references for the analysis via MDGC. In addition, an organic extract of submerged cultivated PSA was used for enantioselective analysis (cf.…”