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Furaneol

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Furaneol
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
CAS Number
3D model (JSmol)
Abbreviations DMHF
ChEBI
ChemSpider
ECHA InfoCard 100.020.826 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3Key: INAXVXBDKKUCGI-UHFFFAOYSA-N
  • InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3Key: INAXVXBDKKUCGI-UHFFFAOYAH
SMILES
  • O=C1C(\O)=C(/OC1C)C
Properties
Chemical formula C6H8O3
Molar mass 128.127 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 malodorous at high concentrations, it exhibits a sweet strawberry aroma when dilute. It is found in strawberries 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, and tomato. Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.

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.

Stereoisomers of furaneol
(S)-Furaneol
(S)-configuration 		(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

  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.; Hoberg, Edelgard; Rapp, Adolf; Kecke, Steffen (1997). "Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds". Zeitschrift für Lebensmittel-Untersuchung und -Forschung A. 205 (3): 218–223. doi:10.1007/s002170050154. S2CID 96680333.
  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: 120–124. doi:10.1016/j.foodchem.2008.05.048.
  6. 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. PMID 11559136.
  7. Pérez, A. G. (2008). Fruit and Vegetable Flavour. Woodhead Publishing. ISBN 978-1-84569-183-7.
  8. "Strawberry furanone acetate". thegoodscentscompany.com/.
  9. Leffingwell,:John C. Chirality & Odour Perception – The Furaneols.
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