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.[2]

Furaneol[1]
Names
IUPAC name
4-Hydroxy-2,5-dimethyl-3-furanone
Other names
  • 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
  • Alletone
  • Pineapple ketone
  • Strawberry furanone
  • Dimethylhydroxy furanone
Identifiers
3D model (JSmol)
Abbreviations DMHF
ChEBI
ChemSpider
ECHA InfoCard 100.020.826
UNII
Properties
C6H8O3
Molar mass 128.127 g·mol−1
Melting point 73 to 77 °C (163 to 171 °F; 346 to 350 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 important for odour of buckwheat,[5] and tomato.[6]

Stereoisomerism

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

Furaneol
(2 stereoisomers)

(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]

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References
  1. 4-Hydroxy-2,5-dimethyl-3(2H)-furanone at Sigma-Aldrich
  2. Zabetakis, 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.
  3. Ulrich, D. et al. 1995. Analysis of strawberry flavour - Quantification of the volatile components of varieties of cultivated and wild strawberries. Z. Lebensm. UNters. Forsch. 200:217-220
  4. Tokitomo Y, Steinhaus M, Büttner A, Schieberle P (2005). "Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation". Biosci. Biotechnol. Biochem. 69 (7): 1323–30. doi:10.1271/bbb.69.1323. PMID 16041138.
  5. Janes D, Kantar D, Kreft S, Prosen H (2008). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112: 120. doi:10.1016/j.foodchem.2008.05.048.
  6. Buttery, R.G. et al. 2001. Analysis of furaneol in tomato using dynamic headspace sampling with sodium sulfate. J. Agric. Food Chem. 49:4349-4351
  7. John C. Leffingwell: Chirality & Odour Perception - The Furaneols.
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