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Organic Compounds: Vanillin

====The molecular formula of vanillin is C8H8O3. Its molecular weight is 152.147 grams/mole. Vanillin is used as a flavoring in ice cream, baked goods, chocolate, sweets, and drinks. It is put in fragrant items such as perfume and candles. Medicine and cleaning supplies sometimes contain vanillin to replace bad tastes and odors. It can be utilized as a chemical intermediate and is also used in thin layer chromatography as a stain. ====

====Vanillin can be naturally extracted from vanilla bean pods, but this process is extensive and time consuming, usually taking months to accomplish. In order to overcome this obstacle and create an accessible supply of vanillin, various synthesis processes have been developed over the years. Starting in 1874, vanillin was synthesized from eugenol, which is derived from oil of clove. In the 1920’s, lignin, a byproduct of the creation of wood pulp, was used instead of eugenol. This way has been widely discontinued due to adverse effects on the environment. Now, there are many different methods for using guaiacol to synthesize vanillin. One way consists of a two-step process. Guaiacol and glyoxylic acid are reacted to produce vanillyl mandelic acid. This is turned into vanillin through oxidative decarboxylation, which involves the addition of 4-Hydroxy-3-methoxyphenylglyoxylic acid. ====



Natural vanillin on the outside of vanilla pods Vanillin is white or yellow and can be a powder or in the form of needles. It is a solid at standard temperature and pressure. It has a boiling point of 170 degrees Celsius measured at 2000 Pa and a melting point of 82 degrees Celsius. It has a density of 1.056 grams/cm3. Its vapor pressure is 0.009998 mm Hg. Its refractive index is 1.555. Its specific heat of vaporization is 0.357 kJ/g and its specific heat of combustion is 12.16 kJ/g.

Fun Facts: Mayu Yamamoto from the International Medical Center of Japan won the Ig Nobel Chemistry Prize in 2007 for devising a way to obtain vanillin from cow dung. Hershey’s milk chocolate contains vanillin.

Works Cited "Bromination of 4-hydroxybenzaldehyde." //Synthesis of Vanillin//. University of Delaware. Web. 10 May 2012. . "Fast Determination of Vanillin and Its Synthesis." //Dionex.com//. Dionex, 2009. Web. 10 May 2012. . "Vanilla Frost, Crystals, and Givre." //VanillaReview.com Â·//. Web. 10 May 2012. . "Vanillin - PubChem." //Vanillin - PubChem//. NCBI. Web. 10 May 2012. . "Vanillin." //Wikipedia//. Wikimedia Foundation, 22 Apr. 2012. Web. 10 May 2012. . "Vanillin." //Wolfram|Alpha: : Chemical Formula, Density, Melting Point, ...// Wolfram Alpha. Web. 10 May 2012. .