Furaneol, or strawberry furanone, is an
organic compound used in the flavor and perfume industry. It is formally a derivative of
furan. It is a white or colorless solid that is soluble in water and organic solvents.[2]
Odor and occurrence
Although malodorous at high concentrations, it exhibits a sweet
strawberry aroma when dilute.[2] It is found in strawberries[3] and a variety of other fruits and it is partly responsible for the smell of fresh
pineapple.[4]
It is also an important component of the odours of
buckwheat,[5] and
tomato.[6] Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.[7]
Stereoisomerism
Furaneol has two
enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[8]
Stereoisomers of furaneol
(S)-configuration
(R)-configuration
Biosynthesis
It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the
glucoside, derived from dehydration of sucrose.[2]
^
abcZabetakis, I.; Gramshaw, J. W.; Robinson, D. S. (1999). "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry. 65: 139–151.
doi:
10.1016/S0308-8146(98)00203-9.
^Janes D, Kantar D, Kreft S, Prosen H (2008). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112: 120–124.
doi:
10.1016/j.foodchem.2008.05.048.
^Buttery, Ron G.; Takeoka, Gary R.; Naim, Michael; Rabinowitch, Haim; Nam, Youngla (2001). "Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate". Journal of Agricultural and Food Chemistry. 49 (9): 4349–4351.
doi:
10.1021/jf0105236.
PMID11559136.
^Pérez, A. G. (2008). Fruit and Vegetable Flavour. Woodhead Publishing.
ISBN978-1-84569-183-7.