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Furaneol

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.

Odor and occurrence

Although possessed of a caramel-like odor at high concentrations, it exhibits a sweet strawberry aroma when dilute. and a variety of other fruits and it is partly responsible for the smell of fresh pineapple. It is also an important component of the odours of buckwheat,{{cite journal

Furaneol acetate

The acetate ester of furaneol, also known as caramel acetate and strawberry acetate, is also popular with flavorists to achieve a fatty toffee taste and it is used in traces in perfumery to add a sweet gourmand note.

Stereoisomerism

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

[[File:(S)-Furanol V1.svg150px*(S)*-Furaneol]]
(*S*)-configuration[[File:(R)-Furanol V1.svg150px*(R)*-Furaneol]]
(*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.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W317403 4-Hydroxy-2,5-dimethyl-3(2H)-furanone] at [[Sigma-Aldrich]]
  2. Zabetakis, I.. (1999). "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry.
  3. (1997). "Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds". Zeitschrift für Lebensmittel-Untersuchung und -Forschung A.
  4. (2005). "Odor-active constituents in fresh pineapple (''Ananas comosus'' [L.] Merr.) by quantitative and sensory evaluation". Biosci. Biotechnol. Biochem..
  5. (2001). "Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate". Journal of Agricultural and Food Chemistry.
  6. "Strawberry furanone acetate".
  7. Leffingwell,:John C. [http://www.leffingwell.com/chirality/furaneol.htm Chirality & Odour Perception – The Furaneols].
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

flavors enones enols dihydrofurans sweet-smelling-chemicals
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