Ethyl methylphenylglycidate

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Ethyl methylphenylglycidate
Strawberry aldehyde.png
Names
IUPAC name
Ethyl 3-methyl-3-phenyl-oxirane-2-carboxylate
Other names
Ethyl methylphenylglycidate
Strawberry aldehyde
Aldehyde C-16
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.966
Properties
C12H14O3
Molar mass 206.24 g·mol−1
Appearance Colourless to pale yellow liquid
Density 1.09-1.10 g/cm3[1]
Melting point 7 to 8 °C (45 to 46 °F; 280 to 281 K)[1]
Boiling point 272 to 275 °C (522 to 527 °F; 545 to 548 K)[1]
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ethyl methylphenylglycidate, commonly known as "strawberry aldehyde", is an organic compound used in the flavor industry in artificial fruit flavors, in particular strawberry.[2]

Uses[edit]

Because of its pleasant taste and aroma, ethyl methylphenylglycidate finds use in the fragrance industry, in artificial flavors, and in cosmetics.[1] Its end applications include perfumes, soaps, beauty care products, detergents, pharmaceuticals, baked goods, candies, ice cream, and others.

Chemistry[edit]

Ethyl methylphenylglycidate is classified as an ester and an epoxide; but, despite its common name, it is not an aldehyde. It is a colourless to pale-yellow liquid that is insoluble in water.

Ethyl methylphenylglycidate is usually prepared by the condensation of acetophenone and the ethyl ester of monochloroacetic acid in the presence of a base, in a reaction known as the Darzens condensation.

Safety[edit]

Long-term, high-dose studies in rats have demonstrated that ethyl methylphenylglycidate has no significant adverse health effects and is not carcinogenic.[3] The US Food and Drug Administration has classified ethyl methylphenylglycidate as generally recognized as safe (GRAS).[4]

See also[edit]

References[edit]

  1. ^ a b c d Ethyl Methylphenylglycidate, chemicalland21.com
  2. ^ David J. Rowe (2005). Chemistry and technology of flavors and fragrances. ISBN 0-8493-2372-X. 
  3. ^ Dunnington, D; Butterworth, MRS; Gaunt, IF; Mason, PL; Evans, JG; Gangolli, SD (1981). "Long-term toxicity study of ethyl methylphenylglycidate (strawberry aldehyde) in the rat". Food and Cosmetics Toxicology. 19 (6): 691–9. doi:10.1016/0015-6264(81)90522-8. PMID 7327470. 
  4. ^ "Food Additive Status List". Food and Drug Administration.