What molecule am I?
Ethyl methylphenylglycidate is an aromatic organic compound with two functional groups, an ester and an epoxide. It is also known as “strawberry aldehyde” even though it is not found in strawberries and does not contain an aldehyde group. The compound contains two asymmetric centers; the article of commerce is a racemate of all four stereoisomers.
The first known synthesis of ethyl methylphenylglycidate was reported in 1905 by Rainer Ludwig Claisen at the University of Berlin in a lengthy article titled “About some syntheses using sodium amide”. Claisen was a pioneering chemist primarily known for developing condensation and rearrangement reactions that bear his name.
Today, ethyl methylphenylglycidate is synthesized by a method reported in 1961 by Keiiti Sisido, Osamu Nakanisi, and Hitosi Nozaki* at Kyoto University (Japan). They used the Darzens condensation, in which a ketone (acetophenone in this case) is treated with an α-haloester (ethyl chloroacetate) to form the epoxide ring.
Ethyl methylphenylglycidate’s flavor and aroma are reminiscent of strawberries, hence its nickname. It is used not only as an artificial strawberry-flavoring agent, but also in the fragrance industry, particularly in perfumes, personal care products, soaps, and detergents.
So why might you be consuming this molecule on Saturday? January 15 is National Strawberry Ice Cream Day! Be sure to get your fill of ethyl methylphenylglycidate.
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.