Syringol

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
CAS Number	91-10-1
Beilstein Reference	1526871
ChEBI	CHEBI:955
ChEMBL	ChEMBL109652
ChemSpider	6774
EC Number	202-041-1
Jmol interactive 3D	Image
PubChem	7041
UNII	4UQT464H8K
InChI InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3 Key: KLIDCXVFHGNTTM-UHFFFAOYSA-N InChI=1/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3 Key: KLIDCXVFHGNTTM-UHFFFAOYAG
SMILES O(c1cccc(OC)c1O)C
Properties
Chemical formula	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)
Solubility in water	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

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.^[2]

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.^[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

• Phenolic content in wine
• Syringaldehyde
• Syringic acid
• Acetosyringone
• Sinapaldehyde
• Sinapinic acid
• Sinapine
• Canolol

References

1. 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.