Ethyl benzoate

November is flavor and aroma month! It’s almost Thanksgiving! Among the holiday treats that most of us enjoy is cranberry sauce, whether it’s full of whole berries or simply a wiggly gelatin. What compounds are in cranberries that make the sauce taste so good?
According to the Science and Food program at the University of California, Los Angeles, the primary flavor compounds are ethyl benzoate, p-cymene, α-terpineol, and 1,8-cineole (aka eucalyptol). The latter two are former Molecules of the Week, so the first two take center stage this year.

Ethyl benzoate is a simple ester of benzoic acid with a sweet, fruity aroma. It has been known since the late 19th century; it is found in fruits such as apples, bananas, cherries, and of course, cranberries. Synthetic ethyl benzoate is made by esterifying benzoic acid and ethanol with an acid catalyst such as hydrochloric or sulfuric acid. It is used as an ingredient in perfumes and artificial fruit-flavoring agents.

p-Cymene is a dialkyl aromatic hydrocarbon. In addition to being a flavor component in cranberries, it is abundant in several essential oils, notably the oils of cumin and thyme. Its aroma and flavor have been described as having hints of citrus, earth, and wood. It can be synthesized from petrochemicals (e.g., the alkylation of toluene with propylene) or from natural terpenes (e.g., by microwave irradiation of limonene). Like ethyl benzoate, p-cymene is used as a flavoring agent; but it also has medicinal uses (in cough syrup) and as a starting material for manufacturing pesticides.