Ванілін

Identity and properties

Vanillin is 4-hydroxy-3-methoxybenzaldehyde, with CAS number 121-33-5. Its formula is C₈H₈O₃ and its molecular weight is 152.15. The molecule has two functional groups, the phenolic OH and the aldehyde. Its taste is a pleasant vanilla.

Vanillin crystallizes in a monoclinic structure. It is very soluble in ethanol, diethyl ether and acetone, and soluble in benzene and ligroin. It oxidizes slowly and somewhat on exposure to moist air, and light affects it. Alkalies decompose it.

Occurrence

Cured vanilla pods contain about 2% vanillin by dry weight. Real vanilla extract from the seedpod is a complex mixture of several hundred compounds, including vanillin, acetaldehyde, acetic acid, furfural, hexanoic acid, 4-hydroxybenzaldehyde, eugenol, methyl cinnamate and isobutyric acid. Synthetic vanilla essence is a solution of synthetic vanillin in ethanol. Vanillin is also found in Leptotes bicolor, an orchid native to Paraguay and southern Brazil. At lower concentrations, vanillin also contributes to the flavor and aroma of foods as varied as olive oil, butter, raspberry and lychee. Of the vanilla species, only three are relevant as sources of vanillin: Vanilla planifolia, Vanilla pompona and Vanilla tahitensis.

Market and uses

Synthetic vanillin accounts for 88% of the global market, natural vanillin from pods for only 1.5%, and plant-based vanillin for 11.5%. In 2001 the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were produced. Synthetic vanillin sells for around 10-20 USD/kg. Natural vanillin costs from a minimum of USD 1250/kg to 4400/kg.

Vanillin has antimicrobial properties and acts synergistically with conventional preservatives. Its phenolic OH and aldehyde groups may act as handles for chemical reactions, so vanillin can take part in polymerisation reactions that yield bio-based polymers and resins. Vanillin may also be a starting molecule for specialised molecules, among them capsaicin and piperonal (heliotropine).

Labelling in the EU

In July 2023 the European Commission published Regulation 2023/1545, which amends the EU Cosmetics Regulation 1223/2009 and adds fragrance allergens, vanillin among them, that were previously not subject to individual labeling. In the EU, these allergens must be named in the ingredient list when present above 0.01% in a rinse-off cosmetic and above 0.001% in a leave-on cosmetic.

Ethyl vanillin

Ethyl vanillin is 3-ethoxy-4-hydroxybenzaldehyde, CAS 121-32-4. It is a homologue of vanillin that carries an ethoxy group on the 3 position where vanillin has a methoxy group. As a flavorant, ethyl vanillin is about three times as potent as vanillin and is used in the production of chocolate. Its aroma is described as sweet, creamy, vanilla, caramellic and root beer.

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