Vanillin
Encyclopedia : V : VA : VAN : Vanillin
| Vanillin | |
|---|---|
| |
| General | |
| Systematic name | 4-hydroxy-3-methoxybenzaldehyde |
| Other names | Vanillin vanillic aldehyde Methyl vanillin |
| Molecular formula | C8H8O3 |
| SMILES | O=CC1=CC(OC)=C(O)C=C1 |
| Molar mass | 152.14 g/mol |
| Appearance | White or lightly yellow solid |
| CAS number | [121-33-5] |
| Properties | |
| Density and phase | 1.056 g/cm3, solid |
| Solubility in water | 1 g/100 ml (25°C) |
| Melting point | 80-81°C (353-354 K) |
| Boiling point | 285°C (558 K) |
| Acidity (pKa) | 7.396 |
| Viscosity | ? cP at ?°C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | 147°C |
| R/S statement | R: R22. S: S24/25. |
| RTECS number | YW5775000 |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | [1H NMR] [13C NMR] |
| 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) [Chemical infoboxInfobox disclaimer and 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 alcohol. 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-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. Isomerization to isoeugenol, followed by oxidation provides vanillin. Currently, the industrial processes for creating vanillin involve formylation of guaiacol (by the Reimer-Tiemann reaction) and also the fermentation of 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.
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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