Everything about Vanillin totally explained
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Vanillin,
methyl vanillin, or
4-hydroxy-3-methoxybenzaldehyde, is an
organic compound with the molecular formula C
8H
8O
3. Its
functional groups include
aldehyde,
ether and
phenol. It is the primary component of the extract of the
vanilla bean. Synthetic vanillin is used as a
flavoring agent in foods, beverages, and pharmaceuticals.
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-CH
2CH
3) instead of a methoxy group (-O-CH
3).
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 from either the
petrochemical guaiacol, or from
lignin, a natural constituent of
wood which is a byproduct of the
paper 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, the
Aztecs used it as a flavoring for
chocolate. Europeans became aware of both chocolate and vanilla around the year 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 from
guaiacol. 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, isn't 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 smaller concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as
olive oil,
butter, and
raspberry and
lychee fruits. Aging in
oak (wine) barrels imparts vanillin to some
wines and
spirits. In other foods, heat treatment evolves 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.
Production
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.
Madagascar is presently the largest producer of natural vanillin.
As harvested, the green seed pods contain vanillin in the form of its β-D-
glycoside; the green pods don't 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're 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. 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've 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.
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. The remainder was produced by
chemical synthesis. 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. Vanillin was commercially produced from eugenol until the 1920s. Later it was synthesized from
lignin-containing "brown liquor", a byproduct of the
sulfite process for making
wood pulp. 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. Several routes exist for synthesizing vanillin from guaiacol. 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. The resulting vanilmandelic acid is then converted to vanillin by oxidative decarboxylation. 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.
Uses
The largest single 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.
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.
Further Information
Get more info on 'Vanillin'.
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