Syringol

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

Syringol[1]
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 (JSmol)
1526871
ChEBI
ChEMBL
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
Density 1.15857 g/cm3 (60 °C) [2]
Melting point 50 to 57 °C (122 to 135 °F; 323 to 330 K)
Boiling point 262 °C (504 °F; 535 K) [2]
Slightly soluble
Vapor pressure 15.8 Pa (60 °C) [2]
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

Natural occurrence

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

Food preparation

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.[3]

Chemical feedstock

Pyrolysis oil, a biofuel derived from woody biomass, can be optimized to yield syringol as a byproduct, potentially replacing demand for petroleum derived phenols.[4] For instance, studies indicate that syringol can serve as a substitute feedstock for phenol formaldehyde resin, a commonly used, water resistant adhesive for plywood.[5]

See also

References
  1. 2,6-Dimethoxyphenol at Sigma-Aldrich
  2. Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. doi:10.1007/s10765-019-2570-9.
  3. Mrak, E. M., Chichester, C. O., & Schweigert (1984). Advances in Food Research, Volume 29. London: Academic Press, Inc. pp. 129–130. ISBN 9780080567488.CS1 maint: uses authors parameter (link)
  4. 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.
  5. 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.
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