Furaneol, or strawberry furanone, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

used in the flavor and perfume industry. It is formally a derivative of

furan Furan is a Heterocyclic compound, heterocyclic organic compound, consisting of a five-membered aromatic Ring (chemistry), ring with four carbon Atom, atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as f ...

. It is a white or colorless solid that is soluble in water and organic solvents.

Odor and occurrence

Although malodorous at high concentrations, it exhibits a sweet

strawberry The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown Hybrid (biology), hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit ...

aroma when dilute. It is found in strawberries and a variety of other fruits and it is partly responsible for the smell of fresh

pineapple The pineapple (''Ananas comosus'') is a Tropical vegetation, tropical plant with an edible fruit; it is the most economically significant plant in the family Bromeliaceae. The pineapple is indigenous to South America, where it has been culti ...

. It is also an important component of the odours of

buckwheat Buckwheat (''Fagopyrum esculentum'') or common buckwheat is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. Buckwheat originated around the 6th millennium BCE in the region of what ...

, and

tomato The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible Berry (botany), berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originate ...

. Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.

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.

Stereoisomerism

Furaneol has two

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s, (''R'')-(+)-furaneol and (''S'')-(−)-furaneol. The (''R'')-form is mainly responsible for the smell.Leffingwell,:John C
Chirality & Odour Perception – The Furaneols

Biosynthesis

It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the

glucoside A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. Th ...

, derived from dehydration of sucrose.

References

{{Reflist Flavors Enones Enols Dihydrofurans Sweet-smelling chemicals