Home > Vanillin (Molecule of the Month for March 2007 )

Picture of Vanillin

click on the picture above to interact
with the 3D model of the
Vanillin structure
(this will open a new browser window)

Picture of Vanillin

C8 H8 O3

Vanillin is the primary chemical component of the extract of the vanilla bean. Synthetic vanillin is used as a flavoring agent in foods, beverages, and pharmaceuticals. Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. The largest single use of vanillin is as a flavoring, usually in sweet foods. The ice cream and chocolate industries together comprise 75% of the market for vanillin as a flavoring, with smaller amounts being used in confections and baked goods.

Vanilla was cultivated as a flavoring by precolumbian Mesoamerican peoples; at the time of their conquest by Hernándo Cortés, the Aztecs used it as a flavoring for chocolate. Europeans became aware of both chocolate and vanilla around the year 1520. Natural vanillin is extracted from the seed pods of Vanilla planifola, a vining orchid native to Mexico, but now grown in tropical areas around the globe. Madagascar is presently the largest producer of natural vanillin. As harvested, the green seed pods contain vanillin in the form of its ?-D-glycoside; the green pods do not have the flavor or odor of vanilla. After being harvested, their flavor is developed by a months-long curing process.

The demand for vanilla flavoring has long exceeded the supply of vanilla beans. As of 2001, the annual demand for vanillin was 12,000 tons, but only 1800 tons of natural vanillin were produced. The remainder was produced by chemical synthesis. Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin was commercially produced from eugenol until the 1920s. Later it was synthesized from lignin-containing sulfite liquor, a byproduct of wood pulp processing in paper manufacture. While some vanillin is still made from lignin wastes, most synthetic vanillin is today synthesized in a two-step process from the petrochemical precursors guaiacol and glyoxylic acid

Formal Chemical Name (IUPAC)
4-hydroxy-3-methoxybenzaldehyde

References

http://en.wikipedia.org/wiki/Vanillin

Update by Karl Harrison
(Molecule of the Month for March 2007 )