Vanillin

Molecular Formula: C8H8O3 Molar Mass: 152.15 g/mol Density: 1.056 g/cm^3 Boiling Point: 285 degrees C Melting Point: 83 degrees C

Vanilin is an organic compound, which is the primary component in vanilla extract. Because of this, it is often used in foods (especially chocolate and ice cream), beverages, and pharmaceuticals as a flavoring agent. It has a floral smell, as well, and is sometimes used in products because of this.

Vanillin as well as ethylvanillin is used by the food industry. The ethyl is more expensive but has a stronger note. It differs from vanillin by having an ethoxy group (–O–CH2CH3) instead of a methoxy group (–O–CH3). 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. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made either from guaiacol or from lignin, a constituent of wood, which is a byproduct of the pulp industry. Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than oil-based flavoring; the difference is due to the presence of acetovanillone in the lignin-derived product, an impurity not found in vanillin synthesized from guaiacol.
 * Vanillin** is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, ether, and phenol. It is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavoring agent in foods, beverages, and pharmaceuticals.

__**History**__ In the 1500's in England England, as well as in Aztec and other ancient South American civilizations, vanilin was used as flavoring in chocolate, as well as vanilla. Not until 1858, however, did Nicolas-Theodore Gobley isolate vanilin as molecule. In 1874, the actual chemical formula was discovered by scientists Haarmann and Tiemann. Starting in the late 19th century, synthesized vanilin became available and is now used in much of what we eat today.

The largest 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. Vanillin is also used in the fragrance industry, in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products. It is also used in the flavor industry, as a very important key note for many different flavors, especially creamy profiles. Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals. In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals, but as of 2004 this use accounts for only 13% of the market for vanillin. Additionally, vanillin can be used as a general purpose stain for developing thin layer chromatography (TLC) plates to aid in visualizing components of a reaction mixture. This stain yields a range of colors for these different components.
 * __Uses__**

__**History**__ Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by Hernán Cortés, the Aztecs used it as a flavoring for chocolate. Europeans became aware of both chocolate and vanilla around 1520. Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley, who obtained it by evaporating a vanilla extract to dryness, and recrystallizing the resulting solids from hot water. In 1874, the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin, a glycoside of isoeugenol found in pine bark. Tiemann and Haarmann founded a company, Haarmann & Reimer (now part of Symrise) and started the first industrial production of Vanillin using their process in Holzminden (Germany). In 1876, Karl Reimer synthesized vanillin (**2**) from guaiacol (**1**) By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available. Synthetic vanillin became significantly more available in the 1930s, when production from clove oil was supplanted by production from the lignin-containing waste produced by the Sulfite pulping process for preparing wood pulp for the paper industry. By 1981, a single pulp and paper mill in Ontario supplied 60% of the world market for synthetic vanillin. However, subsequent developments in the wood pulp industry have made its lignin wastes less attractive as a raw material for vanillin synthesis. 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. Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from rice bran. At $700/kg, this product, sold under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around $15/kg. However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring.

Heat treatment generates vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of coffee, maple syrup and whole grain products including corn tortillas and oatmeal.

An example of where vanilin can be found in is mainly found in plants. The most common plant to find vanilin would be the vanilla bean plant.

= Preparation of Vanillin = Weigh 200 mg of the crude 3-bromo-4-hydroxybenzaldehyde, and transfer it to a 5 mL reaction vial. Add 2.3 mL of the prepared sodium methoxide solution (Combine 113 mL of a 4.0 M sodium methoxide in methanol solution, 4.4 mL of ethyl acetate, and 2.2 g of CuBr). Seal the reaction vial, and heat in the oil bath at 100oC for 1 hour. Cool to room temperature, transfer the contents to a separatory funnel, then acidify with 3 M aqueous HCl until all solids dissolve (approximately 10 mL). Extract this aqueous mixture with 3 x 20 mL of diethyl ether. Combine the organic extracts, dry (Na2SO4), then filter. Add 1.0 g of flash silica gel, and concentrate to a dry powder on the rotary evaporator (use a vacuum adapter with a glass frit!). In the meantime, prepare a 10 g flash silica gel column. Using 10% ethyl acetate in petroleum ether as the solvent, elute the column, collecting 10 x 10 mL fractions, then 25% ethyl acetate in petroleum ether as the solvent, another 10 x 10 mL fractions. Check the fractions by TLC, comparing to an authentic sample of vanillin. It may be necessary to collect more than 15 fractions. Combine the fractions containing only in a tared round bottom flask, and rotary evaporate. Record the mass and percent yield (from 4-hydroxybenzaldehyde), and the melting range of the product. Pure vanillin melts at 81-83 oC.

**Occurances**

Vanillin is most prominent as the principal flavor and aroma compound in vanilla. Cured vanilla pods contain approximately 2% by dry weight vanillin; on cured pods of high quality, relatively pure vanillin may be visible as a white dust or "frost" on the exterior of the pod. It is also found in //Leptotes bicolor//, a species of orchid native to Paraguay and southern Brazil, and the Chinese red pine. At lower concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as olive oil, butter, raspberry and lychee fruits.Aging in oak (wine) barrels imparts vanillin to some wines, vinegar and spirits. In other foods, heat treatment generates vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of coffee, maple syrup, and whole grain products including corn tortillas and oatmeal. Chillin like a vanillin.

The biosynthesis of vanillin is achieved by the conversion of tyrosine into 4-coumaric acid then into ferulic acid and finally into vanillin. Vanillin is then converted into its corresponding glucose ester.

Vanillin can trigger [|migraine headaches] in a small fraction of the people who experience migraines.
 * __Effects:__**