Syringol is the

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 ...

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

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

, 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 a ...

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 Guaiacol () is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs wid ...

, syringol and its derivatives are produced by the

pyrolysis Pyrolysis is a process involving the Bond cleavage, separation of covalent bonds in organic matter by thermal decomposition within an Chemically inert, inert environment without oxygen. Etymology The word ''pyrolysis'' is coined from the Gree ...

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 rigidit ...

. Specifically, syringol is derived from the

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

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 a ...

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 (). The term angiosperm is derived from the Greek words (; 'container, vessel') and (; 'seed'), meaning that the seeds are enclosed within a fruit ...

s. In contrast, pyrolysis of lignin from

gymnosperm The gymnosperms ( ; ) are a group of woody, perennial Seed plant, seed-producing plants, typically lacking the protective outer covering which surrounds the seeds in flowering plants, that include Pinophyta, conifers, cycads, Ginkgo, and gnetoph ...

s gives more

, 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 compound ...

. 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 combusted, and the resulting smoke is typically inhaled to be tasted and absorbed into the bloodstream of a person. Most commonly, the substance used is the dried leaves of the tobacco plant, whi ...

, syringol is the main chemical responsible for the smoky

aroma An odor (American English) or odour (Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive v ...

, 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. Taste is the perception stimulated when a substance in the mouth biochemistry, reacts chemically with taste receptor cells l ...

. 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 Pyrolysis oil, sometimes also known as biocrude or bio-oil, is a synthetic fuel with few industrial applications and under investigation as substitute for petroleum. It is obtained by heating dried biomass without oxygen in a reactor at a temper ...

, a

biofuel Biofuel is a fuel that is produced over a short time span from Biomass (energy), biomass, rather than by the very slow natural processes involved in the formation of fossil fuels such as oil. Biofuel can be produced from plants or from agricu ...

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

s. Some studies indicate that syringol can substitute for

phenol formaldehyde resin Phenol formaldehyde resins (PF), also called phenolic resins or 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 commercial syntheti ...

, a commonly used, water resistant

adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

for

plywood Plywood is a composite material manufactured from thin layers, or "plies", of wood veneer that have been stacked and glued together. It is an engineered wood from the family of manufactured boards, which include plywood, medium-density fibreboa ...

References

{{reflist O-methylated natural phenols

Syringyl/guaiacyl ratio

Food preparation

Chemical feedstock

See also

References