The Rise Of Organic Chemistry

Molecule of the Month - Vanillin

Vanillin, 4-hydroxy-3-methoxybenzaldehyde, is a primary component of the extract of the vanilla bean and is used as a flavoring agent in foods, beverages, and pharmaceuticals. In 1858, Nicolas-Theodore Gobley first isolated vanillin as a relatively pure substance and in 1874, the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure. The aforementioned scientists also synthesized vanillin from coniferin which was shortly followed by other semi-synthetic methods. Today, most vanillin is produced from the petrochemical raw material guaiacol. Several routes exist for synthesizing vanillin from guaiacol. At present, the most significant of these is the two-step process practiced in which guaiacol reacts with glyoxylic acid by electrophilic aromatic substitution. The resulting vanilmandelic acid is then converted to vanillin by oxidative decarboxylation. In October 2007, Mayu Yamamoto of the International Medical Center of Japan won an Ig Nobel prize for developing a way to extract vanillin from cow dung.