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Aspirin conversion to Methyl salicylate

A standard lab experiment in organic chemistry is to convert aspirin(acetylsalicylic acid) to Methyl salicylate. Methyl salicylate(FEMA 2745) is an ester which smells sweet, is strong, is approved for use in food and is the characterizing flavor of wintergreen. Wintergreen flavor is very popular in the United States. Countries like Japan and Italy think it’s most suitable for cleaning bathrooms, but not for eating.

My Impression

Personally, Wintergreen is one of my favorite flavors. It not only adds cool minty flavor, it adds sweetness. You can taste wintergreen in toothpastes, candies, gums, rootbeer, and bubble gum. Yes, that’s right, root beer. Try a swig of rootbeer; doesn’t it taste a little like wintergreen? Rootbeer also has vanilla, ginger, cinnamon, citrus and anise, but the character component is methyl salicylate.

Wintergreen Flavor

Methyl salicylate is best blended in flavors and not added as a single molecule. For example, wintergreen flavor for chewing gum would contain :

25-40% of Methyl salicylate 20-40% peppermint oil 15-40% Menthol an artificial cooling agent modifiers(vanilla, anise, cardamom, cinnamon, ginger, clove et.)

When formulating a wintergreen flavor, the idea is to make it smooth and not harsh. The bits of herbs and spices add interesting side notes that distract the taster from the harshness of the straight chemical while maintaining the overall minty flavor.

Why do flavor chemists use Methyl salicylate in flavors and not wintergreen oil? Methyl salicylate is inexpensive: around $2-3 per pound; while wintergreen oil, which has an extremely limited supply, is closer to $50 per pound.

Wintergreen oil does not smell as clean and sweet as Methyl salicylate, so personally, I prefer the artificial Methyl salicylate. Currently, Methyl salicylate is one of the least expensive mint flavor components. Most mint oils range from $5-30 per pound and very few mint oils are available at low cost artificially.

Some flavor chemists use a little bit of Methyl salicylate in berry or citrus flavors to add a unique character. It’s a confident move that pays off well for many.

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