Wikipedia

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.[2]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.698 Edit this at Wikidata
EC Number
  • 205-167-5
RTECS number
  • CU5760000
UNII
  • InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3 checkY
    Key: KCDXJAYRVLXPFO-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
    Key: KCDXJAYRVLXPFO-UHFFFAOYAW
  • COc1cc(cc(c1O)OC)C=O
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]
GHS07: Exclamation mark
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)
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

  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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