Ethyl methylphenylglycidate

Names
IUPAC name

Ethyl 3-methyl-3-phenyloxirane-2-carboxylate

Other names

Ethyl methylphenylglycidate
Strawberry aldehyde
Aldehyde C-16

Identifiers

CAS Number

* 77-83-8 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 6255

ECHA InfoCard | 100.000.966

PubChem CID

* 6501

UNII |

* UD51D5KR4A Y

CompTox Dashboard (EPA)

* DTXSID8020591

InChI

* 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

SMILES

* CC(C2C(OCC)=O)(O2)C1=CC=CC=C1

Properties

Chemical formula

| 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]

Solubility in water

| Insoluble

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

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 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

[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]

* List of strawberry topics

## 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. Archived from the original on May 31, 2009.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency