Syringol

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Syringol[1]
Syringol
Names
IUPAC name
1,3-Dimethoxy-2-hydroxybenzene
Other names
Syringol
2,6-Dimethoxyphenol
2-Hydroxy-1,3-dimethoxybenzene
Pyrogallol 1,3-dimethyl ether
Identifiers
3D model (Jmol)
1526871
ChEBI
ChemSpider
ECHA InfoCard 100.001.856
EC Number 202-041-1
UNII
Properties
C8H10O3
Molar mass 154.16 g/mol
Appearance Gray to light brown solid
Melting point 50 to 57 °C (122 to 135 °F; 323 to 330 K)
Boiling point 261 °C (502 °F; 534 K)
Slightly soluble
Hazards[1]
Flash point 140 °C (284 °F; 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Syringol is a naturally occurring aromatic organic compound. It is a dimethyl ether of pyrogallol.

Natural occurrence[edit]

Together with guaiacol, syringol and its derivates are characteristic products of pyrolysis of lignin, being derived from the thermal decomposition of the Sinapyl alcohol monomer. As such, syringol is an important component of wood smoke.

Uses[edit]

Food Preparation[edit]

In preparation of food by smoking, syringol is the main chemical responsible for the smoky aroma, while guaiacol contributes mainly to taste. Artificial liquid or solid smoke flavorings also contain the chemical, on average composing 13.73% and 13.42% of those products by mass respectively.[2]

Chemical feedstock[edit]

Pyrolysis oil, a biofuel derived from woody biomass, can be optimized to yield syringol as a byproduct, potentially replacing demand for petroleum derived phenols.[3] For instance, studies indicate that syringol can serve as a substitute feedstock for phenol formaldehyde resin, a commonly used, water resistant adhesive for plywood.[4]

See also[edit]

References[edit]

  1. ^ a b 2,6-Dimethoxyphenol at Sigma-Aldrich
  2. ^ Mrak, E. M., Chichester, C. O., & Schweigert (1984). Advances in Food Research, Volume 29. London: Academic Press, Inc. pp. 129–130. ISBN 9780080567488. 
  3. ^ Dinesh Mohan; Charles U. Pittman Jr.; Philip H. Steele (2006). "Pyrolysis of Wood/Biomass for Bio-oil: A Critical Review". Energy & Fuels. 20 (3): 863. doi:10.1021/ef0502397. 
  4. ^ Bridgwater, A.V.; Effendi A; Gerhauser H (2008). "Production of renewable phenolic resin by thermochemical conversion of biomass: A review". Renewable and Sustainable Energy Reviews. 12 (8). doi:10.1016/j.rser.2007.04.008.