Ethyl methylphenylglycidate

January 10, 2022
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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.

Ethyl methylphenylglycidate hazard information*

Hazard class**GHS code and hazard statement
Skin corrosion/irritation, category 2H315—Causes skin irritationChemical Safety Warning
Skin sensitization, category 1BH317—May cause an allergic skin reactionChemical Safety Warning
Serious eye damage/irritation, category 2AH319—Causes serious eye irritationChemical Safety Warning
Short-term (acute) aquatic hazard, category 2H401— Toxic to aquatic life Chemical Safety Warning
Long-term (chronic) aquatic hazard, category 2H411—Toxic to aquatic life with long-lasting effectsChemical Safety Warning

*Compilation of two safety data sheets.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. Explanation of pictograms.

MOTW update

Dimethyl sulfoxide (DMSO) was the Molecule of the Week for September 20, 2021. It is a valuable laboratory and industrial solvent that has been used and abused as a medical treatment. A 2016 report showed that it may offer relief for autoimmune arthritis patients.

Just recently, another use for DMSO was discovered. Jie-Ping Wan and colleagues at Jiangxi Normal University (Nanchang, China) reported that DMSO is a useful C1 source in organic synthesis. They described an iodine-catalyzed [2 + 2 +1] cascade reaction among enaminones, hydrazines, and DMSO that produces pyrazole derivatives which may prove valuable for making new drugs. DMSO is also the solvent for the reaction.

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Ethyl methylphenylglycidate
fast facts 

CAS Reg. No.77-83-8
2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester
Empirical formulaC12H14O3
Molar mass206.24 g/mol
AppearanceColorless to pale yellow liquid
Boiling point272–275 °C
Water solubility<1 g/L
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