Stereoisomeric Flavor Compounds. 72. Stereoisomeric Distribution of Some Chiral Sulfur-Containing Trace Components of Yellow Passion Fruits

Combinatorial Synthesis by Nature: Volatile Organic Sulfur-Containing Constituents ofRuta chalepensis L.

“…Our findings are in line with previous results. Thus, preference for enantiomers resulting from apparent Si-face addition has been observed for 3-sulfanyl compounds isolated from natural sources other than Ruta (e.g., clary sage [1], passion fruit [19], human axillary sweat [40]), and considerable variations of enantiomer ratios within the same basic structures have been measured [41]. The (S)-configuration at C(4) of 5 suggests that a presumed precursor, namely 4-methylhex-2-enal (or a biological equivalent thereof), is derived from l-isoleucine with retention of the configuration at the center in question.…”

γ(δ)-Thionolactones - Enantioselective Capillary GC and Sensory Characteristics of Enantiomers

“…On the other hand, c(d)-dodecathionolactones show only a slight change in their odor impressions compared with the corresponding lactones. The introduction of the sulfur atom does not increase or generate a tropical fruit note, which is characteristic for some sulfur containing flavor compounds, for example 2-methyl-4-propyl-1,3-oxathiane or 3-(methylthio)hexanol and its esters [7,8,13]. The pure enantiomers of the c(d)-thionolactones exhibit distinct sensorial characteristics, comparable with the lactone enantiomers.…”

“…On the other hand chiral sulfur containing volatiles are among the most important flavor compounds. (4S)-Configured 1,3-oxathianes and (S)-configured 3-mercaptohexyl alkanoates of high enantiomeric purity were detected among the most potent components responsible for the typical tropical-fruity notes of the yellow passion fruit [7,8]. So far, the substitution of oxygen of lactones by sulfur is expected to be of profound influence on flavor quality and potency.…”

Can food quality be enhanced by chromatography?

“…With the help of enantiospecific capillary GC many flavours like that of butter with its content of enantiomeric y(8)-lactones [6] or new flavours like the odour of orchids [7] or of passionfruits like maracuja [8] can now be characterized. This plays an important role in quality control in the aroma industry.…”