:Ethyl methylphenylglycidate
{{chembox
| Watchedfields = changed
| verifiedrevid = 434802513
| Name = Ethyl methylphenylglycidate
| ImageFile = strawberry aldehyde.png
| ImageSize =
| ImageName =
| IUPACName = Ethyl 3-methyl-3-phenyloxirane-2-carboxylate
| OtherNames = Ethyl methylphenylglycidate
Strawberry aldehyde
Aldehyde C-16
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 77-83-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UD51D5KR4A
| SMILES = CC(C2C(OCC)=O)(O2)C1=CC=CC=C1
| PubChem = 6501
| ChemSpiderID = 6255
| StdInChI = 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
| StdInChIKey = LQKRYVGRPXFFAV-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Appearance = Colourless liquid
| C=12|H=14|O=3
| Density = 1.09-1.10 g/cm3[http://chemicalland21.com/specialtychem/perchem/ETHYL%20METHYLPHENYLGLYCIDATE.htm Ethyl Methylphenylglycidate], chemicalland21.com
| MeltingPtC = 7 to 8
| BoilingPtC = 272 to 275
| Solubility = Insoluble
}}
}}
Ethyl methylphenylglycidate, commonly known as strawberry aldehyde, is an organic compound used in the flavor industry in artificial fruit flavors, in particular strawberry.{{cite book | title = Chemistry and technology of flavors and fragrances |author= David J. Rowe | year = 2005 | isbn = 0-8493-2372-X}}
Uses
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.{{cite journal | pmid = 7327470 | doi = 10.1016/0015-6264(81)90522-8 | year = 1981 | last1 = Dunnington | first1 = D | last2 = Butterworth | first2 = MRS | last3 = Gaunt | first3 = IF | last4 = Mason | first4 = PL | last5 = Evans | first5 = JG | last6 = Gangolli | first6 = SD | title = Long-term toxicity study of ethyl methylphenylglycidate (strawberry aldehyde) in the rat. | volume = 19 | issue = 6 | pages = 691–9 | journal = Food and Cosmetics Toxicology}} The US Food and Drug Administration has classified ethyl methylphenylglycidate as generally recognized as safe (GRAS).{{cite web | url = https://www.fda.gov/food/foodingredientspackaging/foodadditives/foodadditivelistings/ucm091048.htm#ftnE | archive-url = https://web.archive.org/web/20090531233802/http://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm#ftnE | url-status = dead | archive-date = May 31, 2009 | title = Food Additive Status List | publisher = Food and Drug Administration}}