Syringaldehyde is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

that occurs in trace amounts widely in nature. Some species of insects use syringaldehyde in their chemical communication systems. ''

Scolytus multistriatus ''Scolytus multistriatus'', the European elm bark beetle or smaller European elm bark beetle, is a bark beetle species in the genus ''Scolytus''. In Europe, while ''S. multistriatus'' acts as vector of the Dutch elm disease, caused by the Ascomyc ...

'' uses it as a signal to find a host tree during oviposition. Because it contains many

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...

s, it can be classified in many ways -

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl gro ...

, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

and polar organic solvents. Its refractive index is 1.53.

Natural sources

Syringaldehyde can be found naturally in the wood of

spruce A spruce is a tree of the genus ''Picea'' (), a genus of about 35 species of coniferous evergreen trees in the family Pinaceae, found in the northern temperate and boreal (taiga) regions of the Earth. ''Picea'' is the sole genus in the subfam ...

and

maple tree ''Acer'' () is a genus of trees and shrubs commonly known as maples. The genus is placed in the family Sapindaceae.Stevens, P. F. (2001 onwards). Angiosperm Phylogeny Website. Version 9, June 2008 nd more or less continuously updated since http ...

s. Syringaldehyde is also formed in oak barrels and extracted into

whisky Whisky or whiskey is a type of distilled alcoholic beverage made from fermented grain mash. Various grains (which may be malted) are used for different varieties, including barley, corn, rye, and wheat. Whisky is typically aged in wooden ca ...

, which it gives spicy, smoky, hot and smoldering wood aromas.

Preparation

This compound may be prepared from

syringol Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, althou ...

by the

Duff reaction The Duff reaction or hexamine aromatic formylation is a formylation reaction used in organic chemistry for the synthesis of benzaldehydes with hexamine as the formyl carbon source. It is named after James Cooper Duff, who was a chemist at the Coll ...

: :

References

Insect pheromones O-methylated natural phenols Hydroxybenzaldehydes Phenol ethers

Natural sources

Preparation

See also

References