Syringaldehyde

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
CAS Number	134-96-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:67380 N
ChEMBL	ChEMBL225303 Y
ChemSpider	8333 Y
ECHA InfoCard	100.004.698
EC Number	205-167-5
PubChem	8655
RTECS number	CU5760000
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/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
Solubility in water	Insoluble
Hazards
Main hazards	Irritant (Xi)
Safety data sheet	External MSDS
S-phrases	S24/25, S28A, S37, S45
NFPA 704	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  (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.

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.

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.

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