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Furaneol





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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

    CAS Number

  • 131222-82-7 (R)-(+)
  • 131222-81-6 (S)-(−)
  • 3D model (JSmol)

    Abbreviations DMHF
    ChEBI
    ChemSpider
    ECHA InfoCard 100.020.826 Edit this at Wikidata

    PubChem CID

    UNII

    CompTox Dashboard (EPA)

    • 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

    Chemical formula

    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 ?)

    Infobox references

    Odor and occurrence

    edit

    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]

    Stereoisomerism

    edit

    Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[8]

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

    Biosynthesis

    edit

    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

    edit
  • ^ 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.
  • ^ 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.
  • ^ 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.
  • ^ 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.
  • ^ 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.
  • ^ Pérez, A. G. (2008). Fruit and Vegetable Flavour. Woodhead Publishing. ISBN 978-1-84569-183-7.
  • ^ Leffingwell,:John C. Chirality & Odour Perception – The Furaneols.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Furaneol&oldid=1215081882"
     



    Last edited on 23 March 2024, at 00:02  





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    This page was last edited on 23 March 2024, at 00:02 (UTC).

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