Furaneol

• 4 -hydroxy-2 ,5-dimethyl- 3 (2H) -furanone
• Strawberry furanone
• Alleton
• HD3F

White to pale yellow solid

Fixed

73-77 ° C

Attention

1608 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Furaneol is a naturally occurring chemical compound from the group of furanones. The name is a registered trademark of Firmenich SA Geneva, the chemical name is 4- hydroxy-2 ,5- dimethylfuran - 3-one.

Occurrence

Furaneol occurs naturally in strawberries and a variety of other fruits. So it is partly responsible for the smell of fresh pineapple. It is also important for the smell of buckwheat and tomatoes.

Production and representation

For the synthesis of furaneol various reactions are known.

It was first in 1963 by Hodge et. al. synthesized by a Maillard reaction of rhamnose with piperidine and 1965 demonstrated by Rodin in pineapple.

It can also be obtained by a five-step reaction starting from tartaric acid in low yield. The crucial step is the intermediate formation of ( 4R, 5R ) -4,5- diacetyl -2 ,2-dimethyl- 1 ,3-dioxolane by reacting methyl magnesium chloride with the corresponding 4,5 -bis ( dimethylamide ).

It is likewise possible synthesis by Elektrohalogenierung a protected Hexindiols ( for example, 3 -hexyne -2 ,5 -diol) in a three-step reaction with 39 -percent yield or the cyclization of Hexadionsystemen (for example, hexane -3 ,4- dione).

Also possible biotechnological representation starting from fructose-1 ,6 -bisphosphate, which is a reaction scheme based, which is very similar to glycolysis.

The biosynthesis in strawberries begins at 6 - over Deoxyfructose Furaneol -glycoside to Furaneol.

Properties

The substance is a white to pale yellow oxidation and heat- sensitive solid. Its flavor is diverse and varies from fruity to strong dilution over caramel- to röstartig in higher concentrations. It comes in two isomeric forms as ( ) - ( 2R)- furaneol and (- ) - ( 2S)- Furaneol before, the odor emanating primarily from the R- form.

Use

Furaneol is used as the flavoring agent. His low odor threshold (nasal: 150 ug / kg, retronasal: 30 mcg / kg water) owes Furaneol its use in the food industry as a flavor component and flavor enhancers for baked products.