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Names | |
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Preferred IUPAC name
4-Hydroxy-3,5-dimethoxybenzaldehyde | |
Other names
3,5-Dimethoxy-4-hydroxybenzene carbonal, Gallaldehyde 3,5-dimethyl ether, 4-Hydroxy-3,5-dimethoxybenzaldehyde, Syringic aldehyde
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.698 |
EC Number |
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PubChem CID
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RTECS number |
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H10O4 | |
Molar mass | 182.17 g/mol |
Appearance | colorless solid |
Density | 1.01 g/cm3 |
Melting point | 110 to 113 °C (230 to 235 °F; 383 to 386 K) |
Boiling point | 192 to 193 °C (378 to 379 °F; 465 to 466 K) at 19 kPa |
Insoluble | |
Hazards | |
GHS labelling:[1] | |
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Warning | |
H302, H315, H319, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | > 110 °C (230 °F; 383 K) c.c. |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Syringaldehyde is an organic compound that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. Scolytus multistriatus uses it as a signal to find a host tree during oviposition.[2]
Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53.[citation needed]
Natural sources
[edit]Syringaldehyde can be found naturally in the wood of spruce and maple trees.[3]
Syringaldehyde is also formed in oak barrels and extracted into whisky, which it gives spicy, smoky, hot and smoldering wood aromas.
Preparation
[edit]This compound may be prepared from syringol by the Duff reaction:[4]
See also
[edit]References
[edit]- ^ "Syringaldehyde". pubchem.ncbi.nlm.nih.gov.
- ^ Vanillin and Syringaldehyde as Attractants for Scolytus multistriatus (Coleoptera: Scolytidae). Meyer H.J. and Norris D.M., Annals of the Entomological Society of America, 17 July 1967, Volume 60, Number 4, pages 858-859, (abstract)
- ^ R.H.J. Creighton; J.L. McCarthy; H. Hibbert (1941). "Aromatic Aldehyde from Spruce and Maple Woods". J. Am. Chem. Soc. 63: 312. doi:10.1021/ja01846a501.
- ^ C. F. H. Allen and Gerhard W. Leubner (1963). "Syringic aldehyde". Organic Syntheses; Collected Volumes, vol. 4, p. 866.