Furaneol Explained

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.^[1]

Odor and occurrence

Although malodorous at high concentrations, it exhibits a sweet strawberry aroma when dilute.^[1] It is found in strawberries^[2] and a variety of other fruits and it is partly responsible for the smell of fresh pineapple.^[3] It is also an important component of the odours of buckwheat,^[4] and tomato.^[5] Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.^[6]

Stereoisomerism

Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.^[7]

Biosynthesis

It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the glucoside, derived from dehydration of sucrose.^[1]

Notes and References

1. 10.1016/S0308-8146(98)00203-9. 2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review . Zabetakis, I. . Gramshaw, J. W. . Robinson, D. S. . Food Chemistry. 1999. 65. 139–151.
2. Ulrich. D.. Hoberg. Edelgard. Rapp. Adolf. Kecke. Steffen. Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds. Zeitschrift für Lebensmittel-Untersuchung und -Forschung A. 205. 3. 1997. 218–223. 10.1007/s002170050154. 96680333.
3. Tokitomo Y, Steinhaus M, Büttner A, Schieberle P . Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation . Biosci. Biotechnol. Biochem. . 69 . 7 . 1323–30 . 2005 . 16041138 . 10.1271/bbb.69.1323. free .
4. Janes D, Kantar D, Kreft S, Prosen H . Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS. Food Chemistry. 112. 120–124. 2008. 10.1016/j.foodchem.2008.05.048.
5. Buttery. Ron G.. Takeoka. Gary R.. Naim. Michael. Rabinowitch. Haim. Nam. Youngla. Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate. Journal of Agricultural and Food Chemistry. 49. 9. 2001. 4349–4351. 11559136. 10.1021/jf0105236.
6. Book: Pérez , A. G. . Fruit and Vegetable Flavour . 2008 . Woodhead Publishing . en . 978-1-84569-183-7.
7. Leffingwell,:John C. Chirality & Odour Perception – The Furaneols.