Syringaldehyde

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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 Edit this at Wikidata
EC Number
  • 205-167-5
RTECS number
  • CU5760000
  • 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 110–113 °C (383–386 K)
Boiling point 192–193 °C at 19 kPa
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant (Xi)
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 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 checkY☒N ?)

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]

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

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.[3]

Preparation

This compound may be prepared by the Duff reaction:[4]

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ http://www.liquorpress.com/2011/04/06/aromatic-substances-of-whisky-syringaldehyde-and-syringa-acid/
  4. ^ C. F. H. Allen and Gerhard W. Leubner (1963). "Syringic aldehyde". Organic Syntheses; Collected Volumes, vol. 4, p. 866.
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