Syringaldehyde is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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 Ascom ...

'' 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 any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

s, it can be classified in many ways -

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

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

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

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 40 species of coniferous evergreen trees in the family Pinaceae, found in the northern temperate and boreal ecosystem, boreal (taiga) regions of the Northern hemisphere. ''Picea'' ...

and

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

s. Syringaldehyde is also formed in

oak An oak is a hardwood tree or shrub in the genus ''Quercus'' of the beech family. They have spirally arranged leaves, often with lobed edges, and a nut called an acorn, borne within a cup. The genus is widely distributed in the Northern Hemisp ...

barrels and extracted into

whisky Whisky or whiskey is a type of liquor made from Fermentation in food processing, fermented grain mashing, mash. Various grains (which may be Malting, malted) are used for different varieties, including barley, Maize, corn, rye, and wheat. Whisky ...

, 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, alth ...

by the Duff reaction: : Duff reaction syringaldehyde

References

Insect pheromones O-methylated natural phenols Hydroxybenzaldehydes Phenol ethers

Natural sources

Preparation

See also

References