Ethyl methylphenylglycidate

• 2,3- epoxy-3- phenylbutyrate
• Erdbeeraldehyd
• Aldehyde C16
• Ethyl methylphenylglycidat
• Methylphenylglycidsäureethylester

• 77-83-8
• 19464-95-0 (2R, 3S)
• 70774-46-8 (2S, 3R)
• 33530-46-0 (2S, 3S)

Colorless to yellowish liquid with a smell of strawberries

Liquid

1.092 g · cm -3

272-275 ° C

Practically insoluble in water

1.505 at 20 ° C.

Attention

5470 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Ethyl-2 ,3- epoxy-3- phenylbutyrate (usually called Erdbeeraldehyd ) is a chemical compound selected from the group of carboxylic acid esters. The somewhat confusing, because false, suffix, the aldehyde is because in the hydrolysis of the ester a glycidic ( the unstable carboxylic acids of the oxirane ) is formed, which rearranges with decarboxylation to an aldehyde.

Production and representation

The compound can be obtained by a two step reaction. First, chloroacetic acid is converted by an acid-catalyzed esterification to ethyl chloroacetate. Then, by a glycidyl ester condensation after GA Darzens obtained from acetophenone and ethyl chloroacetate ester.

Properties

Is a combustible, moisture-sensitive yellow liquid, which is practically insoluble in water. It occurs in two isomeric forms (cis and trans ), which have a different smell. The commercial form represents a mixture of isomers with smell of strawberries

Use

Ethyl -2 ,3 -epoxy- 3- phenylbutyrate is as an approved food preparation and flavoring used in small quantities in perfumery.