Phenol, 2,6-dimethoxy-

• Formula: C₈H₁₀O₃
• Molecular weight: 154.1632
• IUPAC Standard InChI: InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3 Copy

  
• IUPAC Standard InChIKey: KLIDCXVFHGNTTM-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-10-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Pyrogallol 1,3-dimethyl ether; Syringol; 1,3-Dimethoxy-2-hydroxybenzene; 2-Hydroxy-1,3-dimethoxybenzene; 2,6-Dimethoxyphenol; 2,6-Dimethoxyphenyl; 1,3-Dimethyl pyrogallate; 2,6-Dwumetoksyfenol; Pyrogallol dimethylether; 2,6-dimethoxyphenol (syringol); Dimethoxyphenol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lindberg, Jauhiainen, et al., 1972
Lindberg, J.J.; Jauhiainen, T.P.; Savolainen, A., Oxidative coupling of 2,6-disubstituted phenols and the heat of combustion of the resulting products, Pap. Puu, 1972, 54, 91-93. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
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Matos, Miranda, et al., 2003
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Grzybowski, Lamparczyk, et al., 1980
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Shiratsuchi, Shimoda, et al., 1993
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Harrison and Priest, 2009
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Park, Lee, et al., 2004
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Kjällstrand, Ramnäs, et al., 1998
Kjällstrand, J.; Ramnäs, O.; Petersson, G., Gas chromatographic and mass spectrometric analysis of 36 lignin-related methoxyphenols from uncontrolled combustion of wood, J. Chromatogr. A, 1998, 824, 2, 205-210, https://doi.org/10.1016/S0021-9673(98)00698-0 . [all data]

Attia, Grissa, et al., 2012
Attia, S.; Grissa, K.L.; Mailleux, A.C.; Heuskin, S.; Lognay, G.; Hance, T., Acaricidal activities of Santolina africana and Hertia cheirifolia essential oils against the two-spotted spider mite (Tetranychus urticae), Pest Management Sci., 2012, Postprint, 001-011. [all data]

Mondello, 2012
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Robinson, Adams, et al., 2012
Robinson, A.L.; Adams, D.O.; Boss, P.K.; Heymann, H.; Solomon, P.S.; Trengove, R.D., Influence of geographic origine on the sensory characteristics and wine composition of Vitus viniferas cv. Cabernet Sauvignon wines from Australia (Supplemental data), Am. J. Enol. Vitic., 2012, 64, 4, 467-476, https://doi.org/10.5344/ajev.2012.12023 . [all data]

de Simon, Estruelas, et al., 2009
de Simon, B.F.; Estruelas, E.; Munoz, A.M.; Cadahia, E.; Sanz, M., Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage, J. Agric. Food Chem., 2009, 57, 8, 3217-3227, https://doi.org/10.1021/jf803463h . [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Escudero, Gogorza, et al., 2004
Escudero, A.; Gogorza, B.; Melús, M.A.; Ortín, N.; Cacho, J.; Ferreira, V., Characterization of the aroma of a wine from Maccabeo. Key role played by compounds with low odor activity values, J. Agric. Food Chem., 2004, 52, 11, 3516-3524, https://doi.org/10.1021/jf035341l . [all data]

Ferreira, Ortín, et al., 2002
Ferreira, V.; Ortín, N.; Escudero, A.; López, R.; Cacho, J., Chemical characterization of the aroma of grenache Rosé wines: aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies, J. Agric. Food Chem., 2002, 50, 14, 4048-4054, https://doi.org/10.1021/jf0115645 . [all data]

Ansorena, Gimeno, et al., 2001
Ansorena, D.; Gimeno, O.; Astiasarán, I.; Bello, J., Analysis of volatile compounds by GC-MS of a dry fermented sausage: chorizo de Pamplona, Food Res. Int., 2001, 34, 1, 67-75, https://doi.org/10.1016/S0963-9969(00)00133-2 . [all data]

Aznar, López, et al., 2001
Aznar, M.; López, R.; Cacho, J.F.; Ferreira, V., Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions, J. Agric. Food Chem., 2001, 49, 6, 2924-2929, https://doi.org/10.1021/jf001372u . [all data]

Ferreira, Aznar, et al., 2001
Ferreira, V.; Aznar, M.; López, R.; Cacho, J., Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Differences in the odor profiles of four high-quality spanish aged red wines, J. Agric. Food Chem., 2001, 49, 10, 4818-4824, https://doi.org/10.1021/jf010283u . [all data]

Ansorena, Astiasarán, et al., 2000
Ansorena, D.; Astiasarán, I.; Bello, J., Influence of the simultaneous addition of the protease flavourzyme and the lipase novozyme 677BG on dry fermented sausage compounds extracted by SDE and analyzed by GC-MS, J. Agric. Food Chem., 2000, 48, 6, 2395-2400, https://doi.org/10.1021/jf990931y . [all data]

Peterson, 1992
Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

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Caldeira, de Sousa, et al., 2008
Caldeira, I.; de Sousa, R.B.; Balchior, A.P.; Climaco, M.C., A sensory and chemical approach to the aroma of wooden aged Lourinha wine brandy, Ciencia Tec. Vitiv., 2008, 23, 2, 97-110. [all data]

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Williams and Horne, 1995
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Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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