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 ; 131222-82-7 (R)-(+); 131222-81-6 (S)-(−);
3D model (JSmol)	Interactive image;
Abbreviations	DMHF
ChEBI	CHEBI:76247 ;
ChemSpider	18218 ;
ECHA InfoCard	100.020.826
PubChem CID	19309;
UNII	20PI8YZP7A ;
CompTox Dashboard (EPA)	DTXSID0041517 ;
	InChI InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3 Key: INAXVXBDKKUCGI-UHFFFAOYSA-N ; 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). verify (what is ?) 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 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]

References

^ 4-Hydroxy-2,5-dimethyl-3(2H)-furanone at Sigma-Aldrich
^ ^a ^b ^c "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry. 65: 139–151. 1999. doi:10.1016/S0308-8146(98)00203-9. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ 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
^ 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. {{cite journal}}: URL–wikilink conflict (help)
^ 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.
^ 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
^ John C. Leffingwell: Chirality & Odour Perception - The Furaneols.

[1] 4-Hydroxy-2,5-dimethyl-3(2H)-furanone at Sigma-Aldrich

[Zabetakis-2] "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry. 65: 139–151. 1999. doi:10.1016/S0308-8146(98)00203-9. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[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. {{cite journal}}: URL–wikilink conflict (help)

[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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