Ethyl 2,3-epoxy-3-methyl-3-phenylpropanoate

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Structural formula
Structural formula of 2,3-epoxy-3-methyl-3-phenylpropanoic acid ethyl ester
Simplified structural formula without stereochemistry
General
Surname Ethyl 2,3-epoxy-3-methyl-3-phenylpropanoate
other names
  • 2,3-epoxy-3-phenylbutyric acid ethyl ester
  • Ethyl 2,3-epoxy-3-phenyl butyrate
  • Strawberry aldehyde
  • Aldehyde C 16
  • Ethyl methylphenyl glycidate
  • Methylphenylglycidic acid ethyl ester
Molecular formula C 12 H 14 O 3
Brief description

colorless to yellowish liquid with a smell of strawberries

External identifiers / databases
CAS number
  • 77-83-8
  • 19464-95-0 (2 R , 3 S )
  • 70774-46-8 (2 S , 3 R )
  • 33530-46-0 (2 S , 3 S )
EC number 201-061-8
ECHA InfoCard 100,000,966
PubChem 6501
Wikidata Q411450
properties
Molar mass 206.24 g mol −1
Physical state

liquid

density

1.092 g cm −3

boiling point

272-275 ° C

solubility

practically insoluble in water

Refractive index

1.505 (20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-411
P: 261-272-273-280-333 + 313-362-391-501
Toxicological data

5470 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethyl 2,3-epoxy-3-methyl-3-phenylpropanoate (usually called strawberry aldehyde ) is a chemical compound from the group of carboxylic acid esters . The somewhat confusing, because incorrect, name ending aldehyde comes from the fact that the hydrolysis of the ester produces a glycidic acid (the unstable carboxylic acids of oxirane ), which rearranges to form an aldehyde under decarboxylation .

Extraction and presentation

The compound can be obtained by a two-step reaction. First, chloroacetic acid by an acid catalyzed esterification to chloroacetate implemented. The ester is then obtained from acetophenone and ethyl chloroacetate by a glycidate condensation according to GA Darzens .

properties

It is a flammable, moisture-sensitive, yellowish liquid that is practically insoluble in water. It occurs in two isomeric forms ( cis - and trans -), which have a different odor. The commercial form is a mixture of isomers with a strawberry smell.

use

The compound is used as a flavoring substance approved for food preparation and in small quantities in perfumery.

Individual evidence

  1. ↑ a b c d e f g Entry on ethyl 2,3-epoxy-3-phenylbutyrate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  2. ↑ a b c Data sheet Ethyl 3-methyl-3-phenylglycidate, ≥ 98%, FCC from Sigma-Aldrich , accessed on April 16, 2012 ( PDF ).
  3. ↑ Jürgen Nelles: Ethyl 2,3-epoxy-3-phenylbutyrate Preparation of 2,3-epoxy-3-phenylbutyric acid ethyl ester (PDF; 227 kB)
  4. ^ A b Dieter Martinetz, Roland Hartwig: Taschenbuch der Riechstoffe . Harri Deutsch, 1998, ISBN 978-3-8171-1539-6 , pp. 29 ( limited preview in Google Book search).
  5. ↑ Prof. Blum's educational server for chemistry: What the smell of strawberries