Vanillin
Overview
 
Vanillin is a phenolic aldehyde
Phenolic aldehyde
Phenolic aldehydes are a type of natural phenol. Phenolics aldehydes can be found in wines and cognacs.Examples :* Hydroxybenzaldehydes* Protocatechuic aldehyde* Vanillin and isovanillin...

, an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the molecular formula C8H8O3. Its functional groups include aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....

, ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

, and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

. It is the primary component of the extract of the vanilla
Vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...

 bean. It is also found in Leptotes bicolor
Leptotes bicolor
Leptotes bicolor is a species of orchid native to Paraguay and southern Brazil. It is the type species of the genus Leptotes.Its flowers and fruits are used as a substitute for vanilla in milk and ice cream....

, roasted coffee and the Chinese red pine
Chinese Red Pine
The Chinese Red Pine Pinus tabuliformis is a pine native to northern China from Liaoning west to Inner Mongolia and Gansu, and south to Shandong, Henan and Shaanxi, and also northern Korea...

. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavoring agent in foods, beverages, and pharmaceuticals.

Vanillin as well as ethylvanillin
Ethylvanillin
Ethylvanillin is the organic compound with the formula C6H3CHO. This colourless solid consists of a benzene ring with hydroxyl, ethoxy, and formyl groups on the 4, 3, and 1 positions, respectively.- Preparation :...

 is used by the food industry.
Encyclopedia
Vanillin is a phenolic aldehyde
Phenolic aldehyde
Phenolic aldehydes are a type of natural phenol. Phenolics aldehydes can be found in wines and cognacs.Examples :* Hydroxybenzaldehydes* Protocatechuic aldehyde* Vanillin and isovanillin...

, an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the molecular formula C8H8O3. Its functional groups include aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....

, ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

, and phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

. It is the primary component of the extract of the vanilla
Vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...

 bean. It is also found in Leptotes bicolor
Leptotes bicolor
Leptotes bicolor is a species of orchid native to Paraguay and southern Brazil. It is the type species of the genus Leptotes.Its flowers and fruits are used as a substitute for vanilla in milk and ice cream....

, roasted coffee and the Chinese red pine
Chinese Red Pine
The Chinese Red Pine Pinus tabuliformis is a pine native to northern China from Liaoning west to Inner Mongolia and Gansu, and south to Shandong, Henan and Shaanxi, and also northern Korea...

. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavoring agent in foods, beverages, and pharmaceuticals.

Vanillin as well as ethylvanillin
Ethylvanillin
Ethylvanillin is the organic compound with the formula C6H3CHO. This colourless solid consists of a benzene ring with hydroxyl, ethoxy, and formyl groups on the 4, 3, and 1 positions, respectively.- Preparation :...

 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
Eugenol
Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is slightly...

. Today, artificial vanillin is made either from guaiacol
Guaiacol
Guaiacol is a naturally occurring organic compound with the formula C6H4. Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke,...

 or from lignin
Lignin
Lignin or lignen is a complex chemical compound most commonly derived from wood, and an integral part of the secondary cell walls of plants and some algae. The term was introduced in 1819 by de Candolle and is derived from the Latin word lignum, meaning wood...

, a constituent of wood
Wood
Wood is a hard, fibrous tissue found in many trees. It has been used for hundreds of thousands of years for both fuel and as a construction material. It is an organic material, a natural composite of cellulose fibers embedded in a matrix of lignin which resists compression...

, 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.

History

Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by Hernán Cortés
Hernán Cortés
Hernán Cortés de Monroy y Pizarro, 1st Marquis of the Valley of Oaxaca was a Spanish Conquistador who led an expedition that caused the fall of the Aztec Empire and brought large portions of mainland Mexico under the rule of the King of Castile in the early 16th century...

, the Aztecs used it as a flavoring for chocolate
Chocolate
Chocolate is a raw or processed food produced from the seed of the tropical Theobroma cacao tree. Cacao has been cultivated for at least three millennia in Mexico, Central and South America. Its earliest documented use is around 1100 BC...

. 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
Nicolas-Theodore Gobley
Theodore Gobley, who first isolated, and ultimately determined the chemical structure of lecithin, the first identified and characterized member of the phospholipids class, and a pioneer researcher in the study and analysis of the chemical components of brain tissues, was born in Paris on May 11,...

, who obtained it by evaporating a vanilla extract to dryness, and recrystallizing
Recrystallization (chemistry)
-Chemistry:In chemistry, recrystallization is a procedure for purifying compounds. The most typical situation is that a desired "compound A" is contaminated by a small amount of "impurity B". There are various methods of purification that may be attempted , which includes recrystallization...

 the resulting solids from hot water. In 1874, the German scientists Ferdinand Tiemann
Ferdinand Tiemann
Johann Karl Wilhelm Ferdinand Tiemann was a German chemist and together with Reimer discoverer of the Reimer-Tiemann reaction.Beginning in 1866, Tiemann studied pharmacy at the TU Braunschweig where he graduated in 1869...

 and Wilhelm Haarmann
Wilhelm Haarmann
Gustav Ludwig Friedrich Wilhelm Haarmann was a German chemist and together with Karl Ludwig Reimer and Ferdinand Tiemann founded the Haarmann & Reimer chemical plant for the production of vanillin....

 deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin
Coniferin
Coniferin is a glucoside of coniferyl alcohol. This white crystalline solid is a metabolite in conifers, serving as an intermediate in cell wall lignification, as well as having other biological roles....

, a glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...

 of isoeugenol
Isoeugenol
Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang-ylang . It can be synthesized from eugenol and had been used in the manufacture of vanillin. It may occur as either the cis or trans isomer...

 found in pine
Pine
Pines are trees in the genus Pinus ,in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species.-Etymology:...

 bark. Tiemann and Haarmann founded a company, Haarmann & Reimer (now part of Symrise
Symrise
Symrise is a major producer of flavors and fragrances with sales of € 1,572 million in 2010. Major competitors include Firmenich, Givaudan, International Flavors and Fragrances and Takasago International.-History:...

) and started the first industrial production of Vanillin using their process in Holzminden
Holzminden
Holzminden is a town in southern Lower Saxony, Germany. It is the capital of the district of Holzminden. It is located directly on the river Weser, which here is the border to North Rhine-Westphalia.-History:...

 (Germany). In 1876, Karl Reimer synthesized vanillin (2) from guaiacol
Guaiacol
Guaiacol is a naturally occurring organic compound with the formula C6H4. Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke,...

 (1).

By the late 19th century, semisynthetic vanillin derived from the eugenol
Eugenol
Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is slightly...

 found in clove
Clove
Cloves are the aromatic dried flower buds of a tree in the family Myrtaceae. Cloves are native to the Maluku islands in Indonesia and used as a spice in cuisines all over the world...

 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
Lignin
Lignin or lignen is a complex chemical compound most commonly derived from wood, and an integral part of the secondary cell walls of plants and some algae. The term was introduced in 1819 by de Candolle and is derived from the Latin word lignum, meaning wood...

-containing waste produced by the Sulfite pulping process for preparing wood pulp for the paper
Paper
Paper is a thin material mainly used for writing upon, printing upon, drawing or for packaging. It is produced by pressing together moist fibers, typically cellulose pulp derived from wood, rags or grasses, and drying them into flexible sheets....

 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
Guaiacol
Guaiacol is a naturally occurring organic compound with the formula C6H4. Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke,...

 and glyoxylic acid
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially....

.

Beginning in 2000, Rhodia
Rhodia (company)
Rhodia is a group specialized in fine chemistry, synthetic fibers and polymers. Rhodia is listed on the Paris Stock Exchange on NYSE Euronext. The company services the consumer goods, automotive, energy, manufacturing and processes and electronics markets...

 began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid
Ferulic acid
Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell wall components such as arabinoxylans as covalent side chains. It is related to trans-cinnamic acid. As a component of lignin, ferulic acid is a precursor in the...

 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.

Occurrence

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.

At lower concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as olive oil
Olive oil
Olive oil is an oil obtained from the olive , a traditional tree crop of the Mediterranean Basin. It is commonly used in cooking, cosmetics, pharmaceuticals, and soaps and as a fuel for traditional oil lamps...

, butter
Butter
Butter is a dairy product made by churning fresh or fermented cream or milk. It is generally used as a spread and a condiment, as well as in cooking applications, such as baking, sauce making, and pan frying...

, raspberry
Raspberry
The raspberry or hindberry is the edible fruit of a multitude of plant species in the genus Rubus, most of which are in the subgenus Idaeobatus; the name also applies to these plants themselves...

 and lychee
Lychee
The lychee is the sole member of the genus Litchi in the soapberry family, Sapindaceae. It is a tropical and subtropical fruit tree native to Southern China and Southeast Asia, and now cultivated in many parts of the world...

 fruits. Aging in oak (wine) barrels imparts vanillin to some wine
Wine
Wine is an alcoholic beverage, made of fermented fruit juice, usually from grapes. The natural chemical balance of grapes lets them ferment without the addition of sugars, acids, enzymes, or other nutrients. Grape wine is produced by fermenting crushed grapes using various types of yeast. Yeast...

s and spirit
Distilled beverage
A distilled beverage, liquor, or spirit is an alcoholic beverage containing ethanol that is produced by distilling ethanol produced by means of fermenting grain, fruit, or vegetables...

s. In other foods, heat treatment evolves vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of coffee
Coffee
Coffee is a brewed beverage with a dark,init brooo acidic flavor prepared from the roasted seeds of the coffee plant, colloquially called coffee beans. The beans are found in coffee cherries, which grow on trees cultivated in over 70 countries, primarily in equatorial Latin America, Southeast Asia,...

, maple syrup
Maple syrup
Maple syrup is a syrup usually made from the xylem sap of sugar maple, red maple, or black maple trees, although it can also be made from other maple species such as the bigleaf maple. In cold climates, these trees store starch in their trunks and roots before the winter; the starch is then...

, and whole grain
Whole grain
Whole grains are cereal grains that contain cereal germ, endosperm, and bran, in contrast to refined grains, which retain only the endosperm. Whole grains can generally be sprouted while refined grains generally will not sprout. Whole-meal products are made by grinding whole grains in order to make...

 products including corn tortilla
Tortilla
In Mexico and Central America, a tortilla is a type of thin, unleavened flat bread, made from finely ground maize...

s and oatmeal
Oatmeal
Oatmeal is ground oat groats , or a porridge made from oats . Oatmeal can also be ground oat, steel-cut oats, crushed oats, or rolled oats....

.

Natural production

Natural vanillin is extracted from the seed pods of Vanilla
Vanilla
Vanilla is a flavoring derived from orchids of the genus Vanilla, primarily from the Mexican species, Flat-leaved Vanilla . The word vanilla derives from the Spanish word "", little pod...

 planifola
, a vining
Vine
A vine in the narrowest sense is the grapevine , but more generally it can refer to any plant with a growth habit of trailing or scandent, that is to say climbing, stems or runners...

 orchid native to Mexico, but now grown in tropical areas around the globe. Madagascar
Madagascar
The Republic of Madagascar is an island country located in the Indian Ocean off the southeastern coast of Africa...

 is presently the largest producer of natural vanillin.

As harvested, the green seed pods contain vanillin in the form of its β-D-glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...

; 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 details of which vary among vanilla-producing regions, but in broad terms it proceeds as follows:

First, the seed pods are blanched in hot water, to arrest the processes of the living plant tissues. Then, for 1–2 weeks, the pods are alternately sunned and sweated: during the day, they are laid out in the sun, and each night, wrapped in cloth and packed in airtight boxes to sweat. During this process, the pods become a dark brown, and enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...

s in the pod release vanillin as the free molecule. Finally, the pods are dried and further aged for several months, during which time their flavors further develop. Several methods have been described for curing vanilla in days rather than months, although they have not been widely developed in the natural vanilla industry, with its focus on producing a premium product by established methods, rather than on innovations that might alter the product's flavor profile.

Vanillin accounts for about 2% of the dry weight of cured vanilla beans, and is the chief among about 200 other flavor compounds found in vanilla.

Biosynthesis

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.
The conversion of ferulic acid into vanillin is achieved by conversion of the carboxylic acid into a thioester with acetyl-CoA. The feruloyl CoA is then hydrated into 4-hydroxy-3-methoxyphenyl-β-hydroxyprpionyl CoA (HMPHP CoA). At this point, two different pathways have been purposed for the conversion of HMPHP CoA into vanillin. One pathway is similar to the β-oxidation of fatty acid, beginning with the oxidation of the hydroxyl group, cleavage to release acetyl-CoA to form a shortened thioester and then cleavage of the thioester into an aldehyde. The other pathway contains one enzyme that would simultaneously oxidize the hydroxyl group along with the release of aceyl-CoA.

Chemical synthesis

The demand for vanilla flavoring has long exceeded the supply of vanilla beans. , the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were produced. The remainder was produced by chemical synthesis
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...

. Vanillin was first synthesized from eugenol
Eugenol
Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is slightly...

 (found in oil of clove
Clove
Cloves are the aromatic dried flower buds of a tree in the family Myrtaceae. Cloves are native to the Maluku islands in Indonesia and used as a spice in cuisines all over the world...

) 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
Lignin
Lignin or lignen is a complex chemical compound most commonly derived from wood, and an integral part of the secondary cell walls of plants and some algae. The term was introduced in 1819 by de Candolle and is derived from the Latin word lignum, meaning wood...

-containing "brown liquor", a byproduct of the sulfite process
Sulfite process
The sulfite process produces wood pulp which is almost pure cellulose fibers by using various salts of sulfurous acid to extract the lignin from wood chips in large pressure vessels called digesters. The salts used in the pulping process are either sulfites , or bisulfites , depending on the pH...

 for making wood pulp
Wood pulp
Pulp is a lignocellulosic fibrous material prepared by chemically or mechanically separating cellulose fibres from wood, fibre crops or waste paper. Wood pulp is the most common raw material in papermaking.-History:...

. Counter-intuitively, even though it uses waste materials, the lignin process is no longer popular because of environmental concerns, and today most vanillin is produced from the petrochemical
Petrochemical
Petrochemicals are chemical products derived from petroleum. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as corn or sugar cane....

 raw material guaiacol
Guaiacol
Guaiacol is a naturally occurring organic compound with the formula C6H4. Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke,...

. Several routes exist for synthesizing vanillin from guaiacol.

At present, the most significant of these is the two-step process practiced by Rhodia
Rhodia (company)
Rhodia is a group specialized in fine chemistry, synthetic fibers and polymers. Rhodia is listed on the Paris Stock Exchange on NYSE Euronext. The company services the consumer goods, automotive, energy, manufacturing and processes and electronics markets...

 since the 1970s, in which guaiacol (1) reacts with glyoxylic acid
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially....

 by electrophilic aromatic substitution
Electrophilic aromatic substitution
Electrophilic aromatic substitution EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile...

. The resulting vanillylmandelic acid (2) is then converted via 4-Hydroxy-3-methoxyphenylglyoxylic acid (3) to vanillin (4) by oxidative decarboxylation.


In October 2007 Mayu Yamamoto of the International Medical Center of Japan won an Ig Nobel Prize
Ig Nobel Prize
The Ig Nobel Prizes are an American parody of the Nobel Prizes and are given each year in early October for ten unusual or trivial achievements in scientific research. The stated aim of the prizes is to "first make people laugh, and then make them think"...

 for developing a way to extract vanillin from cow dung.

Uses

The largest use of vanillin is as a flavoring, usually in sweet
Sweetness
Sweetness is one of the five basic tastes and is almost universally regarded as a pleasurable experience. Foods rich in simple carbohydrates such as sugar are those most commonly associated with sweetness, although there are other natural and artificial compounds that are sweet at much lower...

 foods. The ice cream
Ice cream
Ice cream is a frozen dessert usually made from dairy products, such as milk and cream, and often combined with fruits or other ingredients and flavours. Most varieties contain sugar, although some are made with other sweeteners...

 and chocolate
Chocolate
Chocolate is a raw or processed food produced from the seed of the tropical Theobroma cacao tree. Cacao has been cultivated for at least three millennia in Mexico, Central and South America. Its earliest documented use is around 1100 BC...

 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 perfume
Perfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

s, and to mask unpleasant odors or tastes in medicines, livestock fodder
Fodder
Fodder or animal feed is any agricultural foodstuff used specifically to feed domesticated livestock such as cattle, goats, sheep, horses, chickens and pigs. Most animal feed is from plants but some is of animal origin...

, and cleaning products. It is also used in the flavor industry, as a very important key note for many different flavors, specially creamy profiles.

Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals
Fine chemicals
Fine chemicals are pure, single chemical substances that are commercially produced with chemical reactions for highly specialized applications. Fine chemicals produced can be categorized into active pharmaceutical ingredients and their intermediates, biocides, and specialty chemicals for technical...

. 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
Thin layer chromatography
Thin layer chromatography is a chromatography technique used to separate mixtures. Thin layer chromatography is performed on a sheet of glass, plastic, or aluminum foil, which is coated with a thin layer of adsorbent material, usually silica gel, aluminium oxide, or cellulose...

 (TLC) plates to aid in visualizing components of a reaction mixture. This stain yields a range of colors for these different components.

Adverse effects

Vanillin can trigger migraine headaches in a small fraction of the people who experience migraines.
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