Syringaldehyde

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.[1]

Syringaldehyde
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.698
EC Number
  • 205-167-5
RTECS number
  • CU5760000
UNII
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
Main hazards Irritant (Xi)
Safety data sheet External MSDS
S-phrases (outdated) S24/25, S28A, S37, S45
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point > 110 °C (230 °F; 383 K) c.c.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.[2]

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:[3]

gollark: Yes.
gollark: They can't handle DE's sheer balance and amazingness.
gollark: Plus Nuclear Chaotic Armor, obviously.
gollark: Yes. WIth maximum balance.
gollark: I think lots of people *don't* like it but it just gets shoved in.

See also

References
  1. 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)
  2. 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.
  3. C. F. H. Allen and Gerhard W. Leubner (1963). "Syringic aldehyde". Organic Syntheses.; Collective Volume, 4, p. 866
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