# Syringol

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Syringol
> Markdown URL: https://mediated.wiki/source/Syringol.md
> Source: https://en.wikipedia.org/wiki/Syringol
> Source revision: 1314859524
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedimages = changed
| Watchedfields = changed
| verifiedrevid = 470475699
| Chembox_ref =<ref name=Aldrich>[https://www.sigmaaldrich.com/US/en/product/aldrich/d135550 2,6-Dimethoxyphenol] at [Sigma-Aldrich](/source/Sigma-Aldrich)</ref>
| Name = Syringol
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Syringol.png
| ImageSize = 150px
| ImageName = Syringol
| PIN = 2,6-Dimethoxyphenol
| OtherNames = Syringol<br />2-Hydroxy-1,3-dimethoxybenzene<br />Pyrogallol 1,3-dimethyl ether
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 955
| SMILES = O(c1cccc(OC)c1O)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6774
| PubChem = 7041
| EC_number =  202-041-1
| Beilstein = 1526871
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4UQT464H8K
| InChI = 1/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
| InChIKey = KLIDCXVFHGNTTM-UHFFFAOYAG
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 109652
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KLIDCXVFHGNTTM-UHFFFAOYSA-N
| CASNo = 91-10-1
| CASNo_Ref = {{cascite|correct|CAS}}
  }}
|Section2={{Chembox Properties
| Formula = C<sub>8</sub>H<sub>10</sub>O<sub>3</sub>
| MolarMass = 154.16 g/mol
| Appearance = colorless solid
| Density = 1.15857 g/cm<sup>3</sup> (60 °C) <ref name="Baird2019">{{cite journal |last1=Baird |first1=Zachariah Steven |last2=Uusi-Kyyny |first2=Petri |last3=Pokki |first3=Juha-Pekka |last4=Pedegert |first4=Emilie |last5=Alopaeus |first5=Ville |title=Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds |journal=International Journal of Thermophysics |date=6 Nov 2019 |volume=40 |issue=11 |page=102 |doi=10.1007/s10765-019-2570-9|bibcode=2019IJT....40..102B |doi-access=free }}</ref>
| MeltingPtC = 50 to 57
| MeltingPt_notes = 
| BoilingPtC = 262
| BoilingPt_ref = <ref name="Baird2019" />
| VaporPressure = 15.8 Pa (60 °C) <ref name="Baird2019" />
| Solubility = Slightly soluble
}}
|Section3={{Chembox Hazards
| Hazards_ref =<ref name=Aldrich/>
| FlashPtC = 140
  }}
}}

'''Syringol''' is the [organic compound](/source/organic_compound) with the formula HO(CH<sub>3</sub>O)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>.  The molecule is a [phenol](/source/phenols), with [methoxy](/source/methoxy) groups in the flanking (2 and 6) positions.  It is the symmetrically [dimethylated derivative](/source/methylation) of [pyrogallol](/source/pyrogallol).  It is a colorless solid, although typical samples are brown owing to air-oxidized impurities. Together with [guaiacol](/source/guaiacol), syringol and its derivatives are produced by the [pyrolysis](/source/pyrolysis) of [lignin](/source/lignin). Specifically, syringol is derived from the [thermal decomposition](/source/thermal_decomposition) of the [sinapyl alcohol](/source/sinapyl_alcohol) component. As such, syringol is a main component of [wood smoke](/source/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](/source/angiosperm)s.  In contrast, pyrolysis of lignin from [gymnosperm](/source/gymnosperm)s gives more [guaiacol](/source/guaiacol), resulting from conversion of [coniferyl alcohol](/source/coniferyl_alcohol).  These lignins have a high guaiacyl (or G) content.<ref name=TPC>{{cite journal |doi=10.1105/tpc.010111|title=The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase |year=2001 |last1=Li |first1=Laigeng |last2=Cheng |first2=Xiao Fei |last3=Leshkevich |first3=Jacqueline |last4=Umezawa |first4=Toshiaki |last5=Harding |first5=Scott A. |last6=Chiang |first6=Vincent L. |journal=The Plant Cell |volume=13 |issue=7 |pages=1567–1586 |pmid=11449052 |pmc=139549 }}</ref>

==Food preparation==
In preparation of food by [smoking](/source/smoking_(food)), syringol is the main chemical responsible for the smoky [aroma](/source/aroma), while guaiacol contributes mainly to [taste](/source/taste). Artificial liquid or solid smoke flavorings also contain these chemicals, on average composing 13.73% and 13.42% of those products by mass respectively.<ref>{{cite book |editor=Chichester, C. O. |editor2=Mrak, E. M. |editor3=Schweigert, B. S. |title=Advances in Food Research|volume =29|year=1984|publisher=Academic Press |location=London|isbn=978-0-08-056748-8|pages=129–130|url=https://books.google.com/books?id=PO4DhgFWIuQC}}</ref>

==Chemical feedstock==
[Pyrolysis oil](/source/Pyrolysis_oil), a [biofuel](/source/biofuel) derived from woody biomass, can be optimized to yield syringol as a byproduct, potentially competing with petroleum-derived [phenol](/source/phenol)s.<ref>{{cite journal|author1=Dinesh Mohan |author2=Charles U. Pittman Jr. |author3=Philip H. Steele |title=Pyrolysis of Wood/Biomass for Bio-oil: A Critical Review|journal=Energy & Fuels|year=2006|volume=20|issue=3|page=863|doi=10.1021/ef0502397}}</ref> Some studies indicate that syringol can substitute for [phenol formaldehyde resin](/source/phenol_formaldehyde_resin), a commonly used, water resistant [adhesive](/source/adhesive) for [plywood](/source/plywood).<ref>{{cite journal|last=Bridgwater|first=A.V. |author2=Effendi A |author3=Gerhauser H|title=Production of Renewable Phenolic Resin by Thermochemical Conversion of Biomass: A Review|journal=Renewable and Sustainable Energy Reviews|year=2008|volume=12|issue=8|pages=2092–2116 |doi=10.1016/j.rser.2007.04.008}}</ref>

== See also ==
{{Div col|colwidth=16em}}
*[Phenolic content in wine](/source/Phenolic_content_in_wine)
*[Syringaldehyde](/source/Syringaldehyde)
*[Syringic acid](/source/Syringic_acid)
*[Acetosyringone](/source/Acetosyringone)
*[Sinapaldehyde](/source/Sinapaldehyde)
*[Sinapinic acid](/source/Sinapinic_acid)
*[Sinapine](/source/Sinapine)
*[Canolol](/source/Canolol)
{{Div col end}}

== References ==
{{reflist}}

Category:O-methylated natural phenols

---
Adapted from the Wikipedia article [Syringol](https://en.wikipedia.org/wiki/Syringol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Syringol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.