Guaiacol
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| Guaiacol | |
|---|---|
| Image:Guaiacol2.png | |
| IUPAC name | 2-methoxyphenol |
| Identifiers | |
| CAS number | |
| PubChem | |
| SMILES | COC1=CC=CC=C1O |
| Properties | |
| Molecular formula | C7H8O2 |
| Molar mass | 124.137 |
| Density | (Liquid)1.112 g/cm3(Crystals)1.129 g/cm3 |
| Melting point |
28 °C |
| Boiling point |
204-206 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Guaiacol is a naturally occurring organic compound with the formula C6H4(OH)(OCH3). This colourless aromatic oil is derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin.
Preparation
Guaiacol is synthesized by the di-methylation of catechol followed by selective mono-demethylation.[1]
- C6H4(OH)2 + 2 (CH3O)2SO2 → C6H4(OCH3)2 + 2 HO(CH3O)SO2
- C6H4(OCH3)2 + C2H5SNa → C6H4(OCH3)(OH)
Uses
Guaiacol is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is also used in the preparation of eugenol[2] and vanillin[3].
References
- ↑ R. N. Mirrington and G. I. Feutrill “Orcinol Monomethyl Ether” Organic Syntheses, Collected Volume 6, p.859 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0859.pdf
- ↑ C. F. H. Allen and J. W. Gates, Jr. “o-Eugenol” Organic Syntheses, Collected Volume 3, p.418 (1955).http://www.orgsyn.org/orgsyn/pdfs/CV3P0418.pdf
- ↑ Esposito, Lawrence J.; K. Formanek, G. Kientz, F. Mauger, V. Maureaux, G. Robert, and F. Truchet (1997). "Vanillin". Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition 24. New York: John Wiley & Sons. 812–825.
See also
- Merck Index, 13th Edition, 4568.de:Guajacol
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
