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Topic summary

Vanillin

Names Preferred IUPAC name
4-Hydroxy-3-methoxybenzaldehyde
Other names
Vanillin
Methyl vanillin
Vanillic aldehyde
Identifiers
3D model (JSmol)
472792 ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.004.060EC Number
  • 204-465-2
3596
KEGG
MeSHvanillin
RTECS number
  • YW5775000
UNII
  • InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3
    Key: MWOOGOJBHIARFG-UHFFFAOYSA-N
  • InChI=1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
    Key: MWOOGOJBHIARFG-UHFFFAOYAS
  • c1(C=O)cc(OC)c(O)cc1
Properties C8H8O3Molar mass152.149 g·mol Appearance White solid OdorVanilla, sweet, balsamic, pleasant Density1.056 g/cm Melting point81 °C (178 °F; 354 K) Boiling point285 °C (545 °F; 558 K) 10 g/L log P1.208 Vapor pressure>1 Pa Acidity (pKa) 7.781 Basicity (pKb) 6.216 Structure Monoclinic Thermochemistry −3.828 MJ/mol Hazards GHS labelling: WarningH302, H317, H319P280, P305+P351+P338NFPA 704 (fire diamond)
1
1
0
Flash point147 °C (297 °F; 420 K) Safety data sheet (SDS) ICSC 1740Related compounds
Related compounds
Anisaldehyde
Apocynin
Eugenol
Phenol
Vanillyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the ethanolic extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.

Vanillin and ethylvanillin are used by the food industry; ethylvanillin 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 often an ethanol solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla, synthetic preparation of artificial vanilla flavoring has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol (4-allyl-2-methoxyphenol). Today, artificial vanillin is made either from guaiacol or lignin.

Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than that from guaiacol-based artificial vanilla; the difference is due to the presence of acetovanillone, a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol.

Wikipedia source