Syringaldehyde

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	134-96-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:67380^Y
ChEMBL	ChEMBL225303^Y
ChemSpider	8333^Y
ECHA InfoCard	100.004.698
EC Number	205-167-5
PubChem CID	8655
RTECS number	CU5760000
UNII	2ZR01KTT21^Y
CompTox Dashboard (EPA)	DTXSID2059643
InChI InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3^Y Key: KCDXJAYRVLXPFO-UHFFFAOYSA-N^Y 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
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^3
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:[1]
Pictograms
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)	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 ^YN ?) Infobox references

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

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

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

See also

• Phenolic content in wine
• Syringol
• Syringic acid
• Acetosyringone
• Sinapyl alcohol
• Sinapinic acid
• Sinapaldehyde
• Sinapine
• Canolol

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.