Ethylvanillin

• 3 -ethoxy -4-hydroxybenzaldehyde
• Bourbonal
• FEMA 2464

Colorless flakes with sweet and creamy, flowery smell

Fixed

• 77-78 ° C
• 74-77 ° C

Hardly soluble in water, soluble in ethanol and ether

Attention

Template: Infobox chemical / molecular formula search available

Ethyl vanillin (3- ethoxy -4-hydroxybenzaldehyde, Bourbonal, FEMA 2464 ) is an organic chemical compound with the molecular formula C9H10O3. It is a derivative of benzaldehyde having an additional hydroxyl and an ethoxy group. It differs from vanillin by replacing the methyl group with an ethyl group.

Representation

One common way is the substitution reaction of o- ethoxyphenol (1) with glyoxylic acid, followed by oxidation of the acid ( 2) formed of 4 - hydroxy-3- ethoxyphenylglyoxylsäure (3), which is decarboxylated to ethylvanillin (4).

Properties

Ethyl vanillin occurs as colorless flakes with sweet and creamy, flowery smell and melts at 77-78 ° C. It is poorly soluble in water but soluble in ethanol and ether. Vanillin and ethyl vanillin also have a similar odor, ethyl vanillin is 2-4 times more intense. Vanillin and ethyl vanillin can be separated by thin-layer chromatography well with mixtures of n- hexane and ethyl acetate.

Isomers and structural Related

Isoethylvanillin (3- hydroxy-4- ethoxybenzaldehyde ) is an isomer and differs from the position of the ethoxy ethyl vanillin. Rather than at position 3 is this to be found here at position 4. Hydroxy and ethoxy groups change places compared to ethyl vanillin. The structure corresponds to the analogy. Between vanillin and isovanillin

Ortho ethylvanillin ( Novovanillin, 2- hydroxy-3- ethoxybenzaldehyde ) and is also an isomer different from ethylvanillin by the position of the hydroxy group. The prefix ortho identifies here the position of the hydroxyl group with respect to the aldehyde group; ethyl vanillin in these two groups are in the para position. The structure corresponds to the analogy. Between vanillin and ortho- vanillin

Use

Today ethyl vanillin is used as artificial flavoring instead of the more expensive vanillin. As flavor additive, it is mainly used in ice cream, showers, distributed confectionery and baked goods. According Aromenverordnung it may be added at a maximum of 250 mg / kg certain foods.

For the synthesis of isovanillin is, inter alia, ethyl vanillin (1 ), which is methylated with dimethyl sulfate to the 3- ethoxy -4-methoxybenzaldehyde (2). Of ethyl ether is then selectively cleaved with sulfuric acid.