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Syringaldehyde

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Syringaldehyde
Names
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
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.698 Edit this at Wikidata
EC Number
  • 205-167-5
PubChem CID
RTECS number
  • CU5760000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3Key: KCDXJAYRVLXPFO-UHFFFAOYSA-N
  • InChI=1/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3Key: KCDXJAYRVLXPFO-UHFFFAOYAW
SMILES
  • COc1cc(cc(c1O)OC)C=O
Properties
Chemical formula C9H10O4
Molar mass 182.17 g/mol
Appearance colorless solid
Density 1.01 g/cm
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
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements 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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 0 0
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

Natural sources

Syringaldehyde can be found naturally in the wood of spruce and maple trees.

Syringaldehyde is also formed in oak barrels and extracted into whisky, which it gives spicy, smoky, hot and smoldering wood aromas.

Preparation

This compound may be prepared from syringol by the Duff reaction:

See also

References

  1. "Syringaldehyde". pubchem.ncbi.nlm.nih.gov.
  2. 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)
  3. 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.
  4. C. F. H. Allen and Gerhard W. Leubner (1963). "Syringic aldehyde". Organic Syntheses; Collected Volumes, vol. 4, p. 866.
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