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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1526871
ChEBI	CHEBI:955 ;
ChEMBL	ChEMBL109652 ;
ChemSpider	6774 ;
ECHA InfoCard	100.001.856
EC Number	202-041-1;
PubChem CID	7041;
UNII	4UQT464H8K ;
CompTox Dashboard (EPA)	DTXSID2052607 ;
	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
Density	1.15857 g/cm3 (60 °C)
Melting point	50 to 57 °C (122 to 135 °F; 323 to 330 K)
Boiling point	262 °C (504 °F; 535 K)
Solubility in water	Slightly soluble
Vapor pressure	15.8 Pa (60 °C)
Hazards
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).

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.^[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]

References

^ ^a ^b 2,6-Dimethoxyphenol at Sigma-Aldrich
^ ^a ^b ^c 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.
^ Mrak, E. M., Chichester, C. O., & Schweigert (1984). Advances in Food Research, Volume 29. London: Academic Press, Inc. pp. 129–130. ISBN 9780080567488.
^ 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.
^ 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.

[Aldrich-1] 2,6-Dimethoxyphenol at Sigma-Aldrich

[Baird2019-2] 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.

[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.

[1]

[2]

[3]

[4]

[5]