Vanillin

=Vanillin (a.k.a. 4-hydroxy-3-methoxybenzaldehyde, Vanillaldehyde, Lioxin, p-Vanillin) =

By: Marlana Fuller

**Raw Structure: **toc


**Chemical Properties: **
Molecular Formula: C8H8O3 Molar Mass: 152.14732 Melting Point: 81-83 C Boiling Point: 285 C Density: 1.06 g/cm²

**3-D Model of Compound: **
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**What is Vanillin? **
A natural crystal like substance that is formed on the cured and processed vanilla bean. It has a very sweet & pleasant aroma and a vanilla-like taste. Although over 400 chemical compounds are add to the overall taste & smell of vanilla flavor, vanillin is the most recognizable flavor.

**Historical Background/Discovery: **
Vanillin was first isolated as a pure substance in 1858 by Nicolas-Theodore Gobley. He obtained vanillin by dehydrating a vanilla extract to dryness & recrystallizing the resulting solids from hot water. In 1874, two German scientists named Ferdinand Tiemann & Wilhelm Haarmann deduced its chemical structure and found a synthesis for vanillin from coniferin(glucoside found in pine bark). They also founded the first industrial company that produced Vanillin using their process. As time went on people discovered more and more ways of synthesizing Vanillin.

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Where is it found? **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Cured Vanilla pods contain about 2% of of dry weight vanillin. It is usually visible as a white dust or "frost" on the exterior of the pod. It is also found in Leptotes bicolor, a type of orchid that is native to Paraguay and southern Brazil. Natural vanillin, in the past, was extracted from the seed pods of a Vanilla planifola, an orchid that originally was found in Mexico. Now the orchid is grown in tropical areas all over the world. Madagascar is presently the largest producer of natural vanillin.

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">How is it obtained? **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Pods have to be cured, during this time they become deep brown & enzymes release the vanillin from the glucoside, along with hundreds of other molecules that add to the authentic vanilla aroma. You can also make vanillin. Convenient laboratories synthesis it by involving electrophilic bromination of 4-hydoxybenzaldehyde followed by copper-catalyzed methoxylation. Large-scale industrial syntheses use a classical early method that starts from eugenol.

<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">**What can it be used for?**
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Vanillin is used as an addictive in foods & beverages, including candies, dessert products, chocolate, ice creams, yogurts, diet shakes & soft drinks, and as an aromatic ingredient in candles, incense, potpourri & air fresheners. It is added to some wines, alcoholic liquors, toothpastes & cigarettes. It is also used in the preparation of pharmaceutical drugs to prevent seizures or reduce the severity of them, for hypertension & Parkinson's disease. It is said that vanillin can stimulate one's appetite and enhance weight gain, so they used it to treat appetite loss & feed cattle vanillin.

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Importance: **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Vanillin is a significant key note in many different flavors. Ice cream & chocolate industries together compromise 75% of the market for vanillin as a flavoring. It is also used largely in the fragrance industries, in perfumes, & to mask unpleasant odors & tasks in medicines. It has been used to make other chemicals & it's very important in pharmaceuticals.

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Explanation of Structure/Percent Composition: **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Vanillin contains ONLY covalent bonds.


 * <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Element || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Atomic Mass || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;"># of atoms || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Mass Percent ||
 * <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Hydrogen || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">1.00794 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">8 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">5.300% ||
 * <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Carbon || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">12.0107 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">8 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">63.153% ||
 * <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Oxygen || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">15.9994 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">3 || <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">31.547% ||

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">Reaction Tendencies: **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">**Air & Water Reactions:** Slowly oxidizes on exposure to air; slightly water soluble. <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">New esters of vanillic acid & related acids are usually formed. Vanillin can react very violently with Br2, HClO4 & potassium-tert-butoxide. It is an aldehyde and aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are created by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react to give first peroxo acids & carboxylic acids.

**<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">References: **
<span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">http://www.chm.bris.ac.uk/motm/vanillin/vanillinh.htm <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">http://www.3dchem.com/molecules.asp?ID=307# <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">[] <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">[] <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">[|http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1183#x321] <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">[] <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">[] <span style="color: #800080; font-family: Verdana,Geneva,sans-serif;">http://www.chemicalbook.com/ChemicalProductProperty_EN_CB8262475.htm