Ethyl methylphenylglycidate

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Ethyl methylphenylglycidate
Chemical structure of ethyl methylphenylglycidate Strawberry aldehyde.png
Chemical structure of 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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless 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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Ethyl methylphenylglycidate, commonly known as strawberry aldehyde, is an organic compound used in the flavor industry in artificial fruit flavors, particularly strawberry. [2]

Contents

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; however, despite its common name, it lacks the presence of an aldehyde group. It is a colorless liquid that is insoluble in water. [1]

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. [3]

Safety

Long-term, high-dose studies in rats have demonstrated that ethyl methylphenylglycidate has no significant adverse health effects and is not carcinogenic. [4] The US Food and Drug Administration has classified ethyl methylphenylglycidate as generally recognized as safe (GRAS). [5]

See also

References

  1. 1 2 3 4 5 Ethyl Methylphenylglycidate, chemicalland21.com
  2. ↑ David J. Rowe (2005). Chemistry and technology of flavors and fragrances. ISBN   0-8493-2372-X.
  3. ↑ Domagala, John M.; Bach, Robert D. (1979). "Synthesis and stereochemistry of ethyl (E)-3-methyl-3-phenylglycidate and (E)- and (Z)-1,3-diphenyl-2-buten-1-one oxide". The Journal of Organic Chemistry. 44 (18): 3168–3174. doi:10.1021/jo01332a015.
  4. ↑ 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.
  5. ↑ "Food Additive Status List". Food and Drug Administration. Archived from the original on May 31, 2009.
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