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Ethyl 3-methyl-3-phenylglycidate

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Ethyl 3-methyl-3-phenylglycidate Basic information
Ethyl 3-methyl-3-phenylglycidate Chemical Properties
Safety Information
Ethyl 3-methyl-3-phenylglycidate Usage And Synthesis
  • Chemical Propertiesclear yellow liquid
  • Chemical PropertiesEthyl 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.
  • Chemical PropertiesEthyl methylphenylglycidate on dilution has a strong fruity odor suggestive of strawberry. It has a characteristic, slightly acid taste reminiscent of strawberry.
  • Chemical PropertiesPerennial, 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.
  • OccurrenceHas apparently not been reported to occur in nature.
  • UsesEthyl 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.
  • UsesPerfumery, flavors.
  • PreparationBy reaction of acetophenone and the ethyl ester of monochloroacetic acid in the presence of an alkaline condensing agent.
  • CompositionStrawberry 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.
  • Aroma threshold valuesDetection: 2 ppm
  • Taste threshold valuesTaste characteristics at 1 and 5% sucrose: sweet, ripe, strawberry jam and preserve notes.
  • Taste threshold valuesTaste characteristics at 50 ppm: sweet, berry, strawberry, fruity, tutti-frutti and floral nuances
  • General DescriptionClear, colorless to yellowish liquid with a strawberry-like odor.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileEsters, 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.
  • Fire HazardEthyl 3-methyl-3-phenylglycidate is probably combustible.
  • Trade nameStrawberry pure (Givaudan)
  • Safety ProfileMddly 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 Preparation Products And Raw materials
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