Ethyl methylphenylglycidate

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

Ethyl methylphenylglycidate
Names
IUPAC name
Ethyl 3-methyl-3-phenyloxirane-2-carboxylate
Other names
Ethyl methylphenylglycidate
Strawberry aldehyde
Aldehyde C-16
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.966
UNII
  • InChI=1S/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3
    Key: LQKRYVGRPXFFAV-UHFFFAOYSA-N
  • CC(C2C(OCC)=O)(O2)C1=CC=CC=C1
Properties
C12H14O3
Molar mass 206.241 g·mol−1
Appearance Colourless 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

Uses

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

Ethyl methylphenylglycidate contains ester and epoxide functional groups, despite its common name, lacks presence of an aldehyde. It is a colourless 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

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

References
  1. 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.
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