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
CAS Number	3658-77-3  Y 131222-82-7 (R)-(+) 131222-81-6 (S)-(−)
3D model (JSmol)	Interactive image
Abbreviations	DMHF
ChEBI	CHEBI:76247  N
ChemSpider	18218  Y
ECHA InfoCard	100.020.826
PubChem CID	19309
UNII	20PI8YZP7A  Y
CompTox Dashboard (EPA)	DTXSID0041517
InChI InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3 Y Key: INAXVXBDKKUCGI-UHFFFAOYSA-N Y InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3 Key: INAXVXBDKKUCGI-UHFFFAOYAH
SMILES 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  YN ?) Infobox references

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 possessed of a caramel-like odor 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)-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]

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.