Ethyl methylphenylglycidate on dilution has a strong fruity odor suggestive of strawberry. It has a characteristic, slightly
acid taste reminiscent of strawberry.
Perennial, herbaceous plant; grows wild or cultivated in central–southern Europe, North America and Asia. The plant grows 10 to 20 cm (4 to 8 in.) in height and has thick rhizomes; radical leaves with long, small, white flowers blossoming from April to July; and fleshy, ovoidal, red berries covered with numerous achenes. The only part used is the berries. Strawberry has a sweet–sour taste and a characteristic odor.
Ethyl 3-Methyl-3-phenylglycidate exists as two optically
active pairs of cis- and trans-isomers; each isomer has a characteristic odor
. The commercial product is a racemic mixture of all four isomers and has
a strong, sweetish, strawberry odor. The cis/trans ratio obtained in the Darzens
condensation of acetophenone (R==CH3) and ethyl chloroacetate depends on the
base used in the reaction.
Has apparently not been reported to occur in nature.
Ethyl 3-Methyl-3-phenylglycidate, also known as “strawberry aldehyde”, is commonly used in the flavor industry for artificial fruit flavors, in particular strawberry.
Ethyl 3-methyl-3-phenylglycidate is a synthetic flavoring agent that is a glycidic acid ester. It is a colorless to pale yellow liquid with a strong fruit odor suggestive of strawberries. It is unstable to alkali and moderately stable to weak organic acids. It should be stored in glass, tin, or aluminum containers. It is soluble in fixed oils and in propylene glycol. It is used in flavors for strawberry note and has application in candy, beverages, and ice cream at 6–20 ppm. It is also termed aldehyde c-16.
ChEBI: Phenylmethylglycidic ester is a carboxylic acid and an epoxide.
By reaction of acetophenone and the ethyl ester of monochloroacetic acid in the presence of an alkaline condensing agent.
Strawberry aroma has been the subject of extensive investigation. Several components have been identified, of which only 7% appear to be responsible for the aroma. Strawberry aroma varies widely with the strawberry variety. The most valuable part, aroma, is from wild strawberry.
Taste characteristics at 1 and 5% sucrose: sweet, ripe, strawberry jam and preserve notes.
Taste characteristics at 50 ppm: sweet, berry, strawberry, fruity, tutti-frutti and floral nuances
Clear, colorless to yellowish liquid with a strawberry-like odor.
Esters, such as Ethyl 3-methyl-3-phenylglycidate, react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Ethyl 3-methyl-3-phenylglycidate is probably combustible.
Strawberry pure (Givaudan)
Mddly toxic by
ingestion. Mutation data reported.
Combustible liquid. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALDEHYDES.
Ethyl 3-methyl-3-phenylglycidate is synthesized by Acetophenone by condensation with Ethyl monochloroacetate in an alkaline solution, using sodium as a condensing agent.
Poorly soluble in Propylene glycol, Glycerin and mineral oil, soluble in alcohol, miscible with most perfume and flavor oils.
