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PhytoChemia Acta

Popularization

Ethylvanillin and you

31 March 2017

Alexis St-Gelais, M. Sc, chimiste

Essential oils and other plant-derived fragrant extracts are worth quite a lot of money. It so happens that, in order to boost profits, unscrupulous people alter oils in various ways. This “Adulterants and you” series is there to introduce you to some of the adulterations we encounter. This is because not all of them are necessarily obvious, nor bear the same level of risk for the final consumer.

Vanilla extracts are all over the place, and you can only appreciate their delicious scent. But could it so happen that a vanilla smells a little too good to be true? Meet the highly popular ethylvanillin.

What is it?

Ethylvanillin is simply vanillin with an extra carbon – a methoxy becomes and ethoxy (figure 1). Its preparation parallels that of synthetic vanillin, simply introducing that extra carbon at the beginning of the process, starting from guethol instead of guaiacol [1].

Ethylvanillin synthesis

Figure 1. Synthesis of ethylvanillin, and comparison of its structure with vanillin.

Ethylvanillin is not very costly: as soon as the amount purchased is reasonable, the price drops at less than 40 USD/kg.

What does it do as an adulterant?

Ethylvanillin has been used for decades in the food industry, because it is roughly three times as potently flavorful and fragrant as vanillin. Its scent is slightly different from the latter, and just to demonstrate how much it is used, its scent is best described as “vanilla cake icing”, somewhat sweeter than vanilla from its caramel notes. This is because a tremendous number of food products contain this ingredient.

Ethylvanillin does not exist in nature. When it is encountered in a vanilla extract, it does not arise from the fruit of Vanilla planifolia, but has been added later on. As such, the extract cannot be considered pure and natural anymore, and its organoleptic properties will be affected.

Is it dangerous?

Absolutely not. Ethylvanillin is regarded as a very safe molecule to be used in flavors and aromatic compositions, and has been for decades [2]. The only danger there is to alter an otherwise genuine vanilla extract, which is more precious.

The craving for “all-natural” flavors and fragrances in the last years have in fact had dramatic consequences on the vanilla market. Shortages and unpredictable climatic conditions caused the prices of the vanilla extracts to go all over the place [3]. Using artificial vanillin and ethylvanillin of course does not exactly reproduce the aroma of the natural extract, but can in some instances reduce the pressure on the market.

How do we detect it?

Ethylvanillin is distinct from vanillin on both gas and liquid chromatographic methods, so it can be detected as a single peak with the proper method. When using mass spectrometry, it also features a very unique mass spectrum, which makes it even easier to spot it. The main challenge is to detect relatively low amounts of the compound. Indeed, since it is more potently aromatic than vanillin, only small quantities are sufficient to obtain the desired aroma.

Bottom of the line

Ethylvanillin is an efficient and accessible artificial flavoring agent, that can conveniently be used in foods with no risk. When an all-natural vanilla is required, it can be fairly well detected by various chromatographic techniques. Think of ethylvanillin the next time you eye that yummy vanilla cake at the grocery store!

References

[1] Fahlbusch, K.-G., Hammerschmidt, F.-J., Panten, J., Pickenhagen, W., Schatkowski, D., Bauer, K., Garbe, D., Surburg, H. Flavors and Fragrances. In Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim (Germany), 2002; p. 138-139.

[2] Choi, K. The Flavor Rundown: Natural vs. Artificial Flavors, [On Line], page consulted on March 31, 2017, URL: http://sitn.hms.harvard.edu/flash/2015/the-flavor-rundown-natural-vs-artificial-flavors/

[3] CBS NEWS. Vanilla bean shortage in Madagascar drives up prices in U.S., [On Line], February 14, 2017, page consulted on March 31, 2017, URL: http://www.cbsnews.com/news/vanilla-bean-shortage-madagascar-drives-up-us-prices/

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