Syringol is the

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 ...

with the formula HO(CH₃O)₂C₆H₃. The molecule is a phenol, with

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position ...

groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of

pyrogallol Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols. Production and reac ...

. It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with guaiacol, syringol and its derivatives are produced by the

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''p ...

lignin Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity ...

. Specifically, syringol is derived from the

thermal decomposition Thermal decomposition, or thermolysis, is a chemical decomposition caused by heat. The decomposition temperature of a substance is the temperature at which the substance chemically decomposes. The reaction is usually endothermic as heat is req ...

of the

sinapyl alcohol Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are ...

component. As such, syringol is an important component of wood smoke.

Syringyl/guaiacyl ratio

Lignin, comprising a major fraction of biomass, is sometimes classified according to the syringyl component. Pyrolysis of lignin derived from sinapyl alcohol affords syringol. The conversion involves replacement of the propenyl alcohol substituent of the sinapyl alcohol by hydrogen. A high syringyl (or S) content is indicative of lignin from

angiosperm Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (), commonly called angiosperms. They include all forbs (flowering plants without a woody stem), grasses and grass-like plants, a vast majority of br ...

s. In contrast, pyrolysis of lignin from

gymnosperm The gymnosperms ( lit. revealed seeds) are a group of seed-producing plants that includes conifers, cycads, '' Ginkgo'', and gnetophytes, forming the clade Gymnospermae. The term ''gymnosperm'' comes from the composite word in el, γυμν ...

s gives more guaiacol, resulting from conversion of

coniferyl alcohol Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, c ...

. These lignins have a high guaiacyl (or G) content.

Food preparation

In preparation of food by

smoking Smoking is a practice in which a substance is burned and the resulting smoke is typically breathed in to be tasted and absorbed into the bloodstream. Most commonly, the substance used is the dried leaves of the tobacco plant, which have bee ...

, syringol is the main chemical responsible for the smoky aroma, while guaiacol contributes mainly to

taste The gustatory system or sense of taste is the sensory system that is partially responsible for the perception of taste (flavor). Taste is the perception produced or stimulated when a substance in the mouth reacts chemically with taste recepto ...

. Artificial liquid or solid smoke flavorings also contain these chemicals, on average composing 13.73% and 13.42% of those products by mass respectively.

Chemical feedstock

Pyrolysis oil, a biofuel derived from woody biomass, can be optimized to yield syringol as a byproduct, potentially competing with petroleum-derived

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...

s. Some studies indicate that syringol can substitute for

phenol formaldehyde resin Phenol formaldehyde resins (PF) or phenolic resins (also infrequently called phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first comm ...

, a commonly used, water resistant adhesive for plywood.

References

{{reflist O-methylated natural phenols

Syringyl/guaiacyl ratio

Food preparation

Chemical feedstock

See also

References