2-Methyl-4-propyl-1,3-oxathiane

Trade Names. Applinal (Quest), Fructone (IFF), Jasmaprunat (FI R). cis-2-Methyl-4-propyl-l, 3-oxathiane [59323- 76-1]... 

The impact of commercial yeast strains on wine fermentation leads to the formation of metabolites of yellow passion fruit (Passiflora edulis Sims) 2-methyl-4-propyl-l,3-oxathian 79 (10MI282,98JAFC1076,98MI53). This oxathian exists in four enantiomeric forms, 79a-d, and there are pronounced sensory differences between them (06CRV4099) for their enan-tioselective synthesis, cf. (84HCA947, 85LA1185). It should be mentioned that most of the aforementioned sulfur heterocycles are sold worldwide as fragrances and flavors. 

Oxathian-3-oxid 2-Methyl-4-propyl- E14/1, 829 (S-oxid-Bild.)... 

CIC Green, fruity, fatty esters like (Z)-3-hexenyl butyrate, (Z)-3-hexenyl hexanoate, 2-ethyl hexenoate, 2-ethyl-octenoate form the basic fruity body. Nerol oxide and edulan add an ethereal, fresh, green, sharp, floral topnote. The floral note (mainly in the purple variety) is represented by linalool with a complex of ionone derivatives, mainly beta-ionone, dihydro-beta-ionone, theaspirone, damascenone. The key components for the green, exotic, sulfury topnote of the yellow variety are 2-methyl-4-propyl-l,3-oxathiane and 3-methylthio-l-hexanol. 

Methylthiohexanol and cis/trans-2-methy -4-pvopy -1,3-oxathiane have been reported by Winter et al. [71] to play important roles in the delicate flavour of the yellow passionfruit, in spite of their occurrence in the extreme trace levels. Using complexation GC, the stereoselective analysis of all the four stereoisomers of 2-methyl-4-propyl-l,3-oxathiane was achieved. This was the first direct stereochemical... 

G. Singer, G. Heusinger, O. Frbhlich, P. Schreier and A. Mosandl. Chirality evaluation of 2-methyl-4-propyl-l,3-oxathiane from the yellow passion fruit. J. Agric. Food Chem., 34, 1029-1033 (1986). 

The following S-containing aroma substances have been isolated from the yellow fruit 3-methylthiohexane-l-ol which probably gives rise to 2-methyl-4-propyl-l,3-oxathianes (cis/trans isomers in the ratio of 10 1) (Xa, b Formula 18.39). Of the two cis isomers, only the 2R,4S-isomer (Xb), which has a sulfurous herb-like odor (threshold = 4 pg/kg water), has been found in the fruit. However, the aroma note more typical of passion fruit is exhibited by the 2S,4R-isomer (Xa). 

Additionally, aroma components of some foods are six-membered heterocycles containing an oxygen atom and sulfur in the molecule. An example of such a compound is (2J ,4S)-2-methyl-4-propyl-l,3-oxathiane (8-168), also known as ds-tropathiane, which occurs in the yellow passion fruit Passiflora edulis, f. flavicarpa, Passifloraceae), pineapple Ananas comosus, Bromeliaceae), whisky and white wines. 

The tropical category is one of the most important areas for new discoveries of key impact flavor compounds. Analyses of passion fruit and durian flavors have produced identifications of many potent sulfur aroma compounds (18). Among these is fropathiane, 2-methyl-4-propyl-l,3-oxathiane, which has an odor threshold of 3 ppb (15). For pineapple, 2-propenyl hexanoate (allyl caproate) exhibits a typical pineapple character (11) however, Furaneol, ethyl 3-methyl-thiopropionate, and ethyl-2-methylbutyrate are important supporting character impact compounds (31). The latter ester contributes the background apple note to pineapple flavor. Another character impact compound, allyl 3-cyclohexyl-... 

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