Furaneol

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	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

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)-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]