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Vanillin
IUPAC name
4-Hydroxy-3-methoxybenzaldehyde
Other names
VanilinVanillic aldehydeMethyl 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
152.15 g/mol
Appearance
White or lightly yellow solid(usually in needles)
Density
1.056 g/cm3, solid
Melting point
80-81 (353-354 K)
Boiling point
285 (558 K)
Solubility in water
1 g/100 ml (25)
Solubility in THF, ethanol, methanol
THF 3.549 M, ethanol 2.32 M, methanol 4.17 M
Viscosity
? cP at?
Hazards
MSDS
External MSDS
Main hazards
May cause irritation to skin,eyes, and respiratory tract
NFPA 704
1
1
0
R-phrases
R22.
S-phrases
S24/25.
Flash point
147
Related compounds
Related compounds
Eugenol, Anisaldehyde, Phenol
Except where noted otherwise, data are given formaterials in their standard state(at 25, 100kPa)Infobox references
Vanillin, methyl vanillin, or 4-hydroxy-3-methoxybenzaldehyde, is 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.
Methyl vanillin is used by the food industry as well as ethylvanillin. 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 from either guaiacol or from lignin, a 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.
Contents
1 History
2 Occurrence
3 Production
3.1 Natural production
3.2 Chemical synthesis
4 Uses
5 See also
6 References
7 Notes
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History
Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by Hern Cort, 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, is not cost-competitive with petrochemical vanillin, which sells for around $15/kg. However, unlike vanillin synthesized from lignin or guaiacol, it can…(and so on)
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