Vanillin
IUPAC name	4-Hydroxy-3-methoxybenzaldehyde
Other names	Vanilin Vanillic aldehyde Methyl vanillin
Identifiers
CAS number	[121-33-5]
RTECS number	YW5775000
SMILES	O=CC1=CC(OC)=C(O)C=C1
Properties
Molecular formula	C8H8O3
Molar mass	152. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 15 g/mol
Appearance	White or lightly yellow solid (usually in needles)
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 056 g/cm³, solid
Melting point	80-81°C (353-354 K)
Boiling point	285°C (558 K)
Solubility in water	1 g/100 ml (25°C)
Viscosity	? cP at ?°C
Hazards
MSDS	External MSDS
Main hazards	May cause irritation to skin, eyes, and respiratory tract
NFPA 704	1 1 0
R-phrases	R22. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous
S-phrases	S24/25. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations.
Flash point	147°C
Related compounds
Related compounds	Eugenol, Anisaldehyde, Phenol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Vanillin, methyl vanillin, or 4-hydroxy-3-methoxybenzaldehyde, is an organic compound with the molecular formula C₈H₈O₃. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air Eugenol (C10H12O2 is an allyl chain-substituted Guaiacol. Eugenol is a member of the Phenylpropanoids class of chemical compounds Anisaldehyde, or anisic aldehyde is an Organic compound that consists of a benzene ring substituted with an Aldehyde and a Methoxy group Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. Its functional groups include aldehyde, ether and phenol. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions An aldehyde is an organic compound containing a terminal Carbonyl group. Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" It is the primary component of the extract of the vanilla bean. Vanilla is a Flavoring derived from Orchids of the genus Vanilla native to Mexico. Synthetic vanillin is used as a flavoring agent in foods, beverages, and pharmaceuticals. Flavor or flavour is the sensory impression of a Food or other substance, and is determined

Methyl vanillin is used by the food industry as well as ethyl vanillin. The ethyl is more expensive but has a stronger note, and differs 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. Vanilla is a Flavoring derived from Orchids of the genus Vanilla native to Mexico. 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 (C10H12O2 is an allyl chain-substituted Guaiacol. Eugenol is a member of the Phenylpropanoids class of chemical compounds Today, artificial vanillin is made from either the petrochemical guaiacol, or from lignin, a natural constituent of wood which is a byproduct of the paper industry. Petrochemicals are chemical products made from raw materials of Petroleum or other Hydrocarbon origin Guaiacol is a naturally occurring Organic compound with the formula C6H4(OH(OCH3 Lignin or lignen is a complex Chemical compound most commonly derived from Wood and an integral part of the secondary Cell walls of Plants Wood is hard fibrous lignified structural tissue produced as secondary Xylem in the stems of Woody plants notably trees but also shrubs The global pulp and paper industry is dominated by North American ( United States, Canada) Northern European ( Finland, Sweden

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. ^[1]

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. Hernán Cortés de Monroy y Pizarro 1st Marqués del Valle de Oaxaca ( 1485&ndash December 2, Aztec is a term used to refer to certain ethnic groups of central Mexico, particularly those groups who spoke the Nahuatl language and who achieved political Chocolate ( pronounced or /-ˈələt/ comprises a number of raw and processed foods that are produced from the seed of the tropical Cacao tree Europeans became aware of both chocolate and vanilla around the year 1520. ^[2]

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. Nicolas-Theodore Gobley (b 11 May 1811, d 1 September 1876, Bagnères-de-Luchon France was a French chemist Recrystallization (see also Crystallization) is a physical process that has meanings in Chemistry, Metallurgy and Geology. ^[3] 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. Johann Karl Wilhelm Ferdinand Tiemann was a German chemist and together with Reimer discoverer of the Reimer-Tiemann reaction. Gustav Ludwig Friedrich Wilhelm Haarmann was a German chemist and together with Karl Ludwig Reimer and Ferdinand Tiemann founded the Haarmann & Reimer chemical Coniferin is a Glucoside of Coniferyl alcohol. This white crystalline solid is a metabolite in Conifers, serving as an intermediate in cell wall This article is about the tree For other uses of the term "pine" see Pine (disambiguation. ^[4] 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). Symrise ( is a major producer of Flavors and Fragrances with sales of € 1230 million in 2006 ( preliminary Holzminden (hɔltsˈmɪndən is a town in southern Lower Saxony, Germany. Germany, officially the Federal Republic of Germany ( ˈbʊndəsʁepuˌbliːk ˈdɔʏtʃlant is a Country in Central Europe. In 1876, Karl Reimer synthesized vanillin from guaiacol. Guaiacol is a naturally occurring Organic compound with the formula C6H4(OH(OCH3 ^[5] By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available. Eugenol (C10H12O2 is an allyl chain-substituted Guaiacol. Eugenol is a member of the Phenylpropanoids class of chemical compounds This article is about the Spice; for other meanings see Clove (disambiguation. ^[6]

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. Oil of cloves, also known as Clove oil, is an Essential oil from the Clove plant Syzygium aromaticum. Lignin or lignen is a complex Chemical compound most commonly derived from Wood and an integral part of the secondary Cell walls of Plants Paper is thin material mainly used for writing upon printing upon or packaging By 1981, a single pulp and paper mill in Ontario supplied 60% of the world market for synthetic vanillin. ^[7] 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. Guaiacol is a naturally occurring Organic compound with the formula C6H4(OH(OCH3 Glyoxylic acid or oxoacetic acid is an Organic compound with the Chemical formula C2H2O3 ^[8]

Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from rice bran. Rhodia is an international chemical company based in La Défense, France, a suburb of Paris. Ferulic acid is an Organic compound that is an abundant Phenolic Phytochemical found in plant Cell walls It is a derivative of trans- Bran is the hard outer layer of Grain and consists of combined Aleurone and Pericarp. 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. ^[9] 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 smaller concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as olive oil,^[10] butter,^[11] and raspberry^[12] and lychee^[13] fruits. Olive oil is a fruit oil obtained from the olive ( Olea europaea; family Oleaceae along with Lilacs Jasmine and ash trees Butter is a Dairy product made by churning fresh or fermented Cream or Milk. The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus The Lychee ( Litchi chinensis) also spelled Litchi (the US FDA spelling or Laichi and Lichu, Chinese: 荔枝 Aging in oak (wine) barrels imparts vanillin to some wines and spirits. The use of Oak in Wine plays a significant role in Winemaking and can have a profound effect on the resulting wine impacting the color flavor Wine is an Alcoholic beverage made from the fermentation of Grape juice ^[14] In other foods, heat treatment evolves vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of coffee,^[15] maple syrup,^[16] and whole grain products including corn tortillas^[17] and oatmeal. CoFFEE is an Open source Software for computer supported collaborative learning (CSCL in a digital classroom Maple syrup is a sweetener made from the sap of Maple trees In Canada and the United States it is most often eaten with waffles and pancakes Whole grains are cereal grains that Bran and germ as well as the Endosperm, in contrast to Refined grains, which retain only In Mexico, Central America, the Caribbean, the United States, and Canada, a tortilla is a type of thin unleavened Breakfast cereal health benefits There has been increasing interest in oatmeal in recent years due to its beneficial health effects ^[18]

Production

These green seed pods contain vanillin only in its glycoside form, and lack the characteristic odor of vanilla.

Natural production

Natural vanillin is extracted from the seed pods of Vanilla planifola, a vining orchid native to Mexico, but now grown in tropical areas around the globe. Vanilla is a Flavoring derived from Orchids of the genus Vanilla native to Mexico. A vine is any plant of Genus Vitis (the Grape plants or by extension any similar climbing or trailing plant The United Mexican States ( or commonly Mexico (ˈmɛksɪkoʊ () is a federal constitutional Republic in North America. Madagascar is presently the largest producer of natural vanillin. Madagascar, or Republic of Madagascar (older name Malagasy Republic) is an Island nation in the Indian Ocean off the southeastern

As harvested, the green seed pods contain vanillin in the form of its β-D-glycoside; the green pods do not have the flavor or odor of vanilla. ^[19] 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. Blanching (also spelled blenching) is a cooking term that describes a process of Food preparation wherein the food substance usually a vegetable or fruit is plunged 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 enzymes in the pod release vanillin as the free molecule. Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins 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,^[20] 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.

Chemical synthesis

The demand for vanilla flavoring has long exceeded the supply of vanilla beans. As of 2001, the annual demand for vanillin was 12,000 tons, but only 1800 tons of natural vanillin were produced. Year 2001 ( MMI) was a Common year starting on Monday according to the Gregorian calendar. ^[21] The remainder was produced by chemical synthesis. In Chemistry, chemical synthesis is purposeful execution of Chemical reactions in order to get a product, or several products Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Eugenol (C10H12O2 is an allyl chain-substituted Guaiacol. Eugenol is a member of the Phenylpropanoids class of chemical compounds This article is about the Spice; for other meanings see Clove (disambiguation. Vanillin was commercially produced from eugenol until the 1920s. ^[22] Later it was synthesized from lignin-containing "brown liquor", a byproduct of the sulfite process for making wood pulp. Lignin or lignen is a complex Chemical compound most commonly derived from Wood and an integral part of the secondary Cell walls of Plants The sulfite process produces Wood pulp which is almost pure Cellulose fibers by using various Salts of Sulfurous acid to extract the Lignin Wood pulp is a dry fibrous material prepared by chemically or mechanically separating the fibers which make up Wood. ^[23] 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 raw material guaiacol. Petrochemicals are chemical products made from raw materials of Petroleum or other Hydrocarbon origin Guaiacol is a naturally occurring Organic compound with the formula C6H4(OH(OCH3 ^[24] Several routes exist for synthesizing vanillin from guaiacol. ^[25] At present, the most significant of these is the two-step process practiced by Rhodia since the 1970s, in which guaiacol reacts with glyoxylic acid by electrophilic aromatic substitution. Rhodia is an international chemical company based in La Défense, France, a suburb of Paris. Glyoxylic acid or oxoacetic acid is an Organic compound with the Chemical formula C2H2O3 Electrophilic aromatic substitution or EAS is an Organic reaction in which an atom usually Hydrogen, appended to an aromatic system is replaced The resulting vanilmandelic acid is then converted to vanillin by oxidative decarboxylation. ^[26] 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. The Ig Nobel Prizes are a Parody of the Nobel Prizes and are given each year in early October — around the time the recipients of the genuine Nobel Prizes are ^[27]

Uses

The largest single use of vanillin is as a flavoring, usually in sweet foods. Sweet is one of the five Basic tastes and is almost universally regarded as a pleasurable experience 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. Ice cream or ice-cream (originally iced cream) is a frozen dessert made from Dairy products such as Milk and Cream, combined Chocolate ( pronounced or /-ˈələt/ comprises a number of raw and processed foods that are produced from the seed of the tropical Cacao tree Confectionery is a set of Food items that are rich in Sugar; modern usage may include substances rich in artificial sweeteners as well Baking is the technique of prolonged Cooking of Food by dry heat acting by conduction, and not by radiation, normally in an Oven, ^[28]

Vanillin is also used in the fragrance industry, in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products. Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living In Agriculture, fodder or animal feed is any Foodstuff that is used specifically to feed Domesticated Livestock, such as ^[29]

Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals. A drug, broadly speaking is any chemical substance that when absorbed into the body Fine chemicals are pure single chemical substances that are commercially produced with chemical reactions into highly specialized applications In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals,^[30] but as of 2004 this use accounts for only 13% of the market for vanillin. ^[31]

References

Notes