Furaneol, aroma, pineapple

Re, L., Maurer, B., Ohloff, G. A simple synthesis of 4-hydroxy-2,5-dimethyl-3(2//)-fiiranone (Furaneol), an important aroma compound of pineapple and strawberry. Helv. Chim. Acta 1973, 26, 1882-1894. 

Furaneol and norfuraneol are significant sensorially active substances with low threshold concentrations. They are synthesised and added to numerous aroma compositions with a pleasant sugary, jammy, fruity and caramel flavour reminiscent of cooked strawberries and pineapple, which is where furaneol was identified for the first time (see Section 8.2.11.1.1). 

Pineapple Ananas comosus, Bromeliaceae) aroma consists of about 200 alcohols, esters, lactones, aldehydes, ketones, monoterpenes, sesquiterpenes and other volatiles. About 80% of the total volatile substances are esters. The main components in the green fruit are ethyl acetate, ethyl 3-(methylthio)propionate (8-189) with a distinctive pineapple aroma and ethyl 3-(acetoxy)hexanoate (8-190). The ripe fruit contains, as the main esters, ethyl acetate, (2J ,3i )-butane-2,3-diol diacetate (8-191) and ketone 3-hydroxy-butan-2-one. An important compound for the typical character of pineapple aroma, as in strawberry aroma, is 2,5-dimethyl-4-hydroxy-2//-furan-3-one (furaneol), present as a glycoside, and 2,5-dimethyl-4-methoxy-2H-furan-3-one. 

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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See also in sourсe #XX -- [ , ]

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