Furaneol

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 Edit this at Wikidata
UNII
  • InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3 checkY
    Key: INAXVXBDKKUCGI-UHFFFAOYSA-N checkY
  • InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
    Key: INAXVXBDKKUCGI-UHFFFAOYAH
  • O=C1C(\O)=C(/OC1C)C
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).
☒N verify (what is checkY☒N ?)

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]

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.[8]

Stereoisomerism

Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[9]

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.[2]

References

  1. ^ 4-Hydroxy-2,5-dimethyl-3(2H)-furanone at Sigma-Aldrich
  2. ^ a b c 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.