Syringaldehyde

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Syringaldehyde is an organic compound found in very small amounts in nature. It has an aromatic ring with one aldehyde group, two methoxy groups, and a hydroxyl group. Pure syringaldehyde is a colorless solid.

Key facts
- IUPAC name: 4-Hydroxy-3,5-dimethoxybenzaldehyde
- Other names: syringaldehyde, syringic aldehyde
- Formula: C9H10O4; molar mass about 182 g/mol
- Appearance: colorless solid (impure samples may look yellow)
- Solubility: insoluble in water; soluble in alcohols and other polar solvents
- Melting point: about 110–113 °C; boiling point around 192–193 °C at low pressure

Natural occurrence and uses
- Found in spruce and maple wood; also formed in oak barrels and contributes spicy, smoky aromas to whisky.
- Some insects, such as Scolytus multistriatus, use it as a chemical signal to find host trees.
- Structure: aromatic aldehyde with phenolic and methoxy groups.

Safety and synthesis
- Hazardous: may irritate skin and eyes and can be harmful if swallowed; handle with care.
- Synthesis note: can be made from syringol using the Duff reaction.