Ethyl methylphenylglycidate
| Names | |
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| IUPAC name
Ethyl 3-methyl-3-phenyloxirane-2-carboxylate
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| Other names
Ethyl methylphenylglycidate
Strawberry aldehyde Aldehyde C-16 | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.000.966 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C12H14O3 | |
| Molar mass | 206.241 g·mol−1 |
| Appearance | Colorless 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).
Infobox references
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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]
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
- ^ a b c d e Ethyl Methylphenylglycidate, chemicalland21.com
- ^ David J. Rowe (2005). Chemistry and technology of flavors and fragrances. ISBN 0-8493-2372-X.
- ^ 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.
- ^ 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.
- ^ "Food Additive Status List". Food and Drug Administration. Archived from the original on May 31, 2009.