A yellowish oily aromatic substance, C7H8O2, derived from guaiacum or wood creosote and used chiefly as an expectorant, antiseptic, and local anesthetic.
[GUAIAC(UM) +
guaiacol
Dictionary:
guai·a·col (gwī'ə-kôl', -kōl')  |
n.
A yellowish oily aromatic substance, C7H8O2, derived from guaiacum or wood creosote and used chiefly as an expectorant, antiseptic, and local anesthetic.
A yellowish oily aromatic substance, C7H8O2, derived from guaiacum or wood creosote and used chiefly as an expectorant, antiseptic, and local anesthetic.
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| Dental Dictionary: guaiacol |
n
Catecholomonomethyl ether, which is used as an expectorant and intestinal disinfectant.
| Medical Dictionary: guai·a·col |
(gwī'ə-kôl', -kōl')
n.
n.
A yellowish, oily, aromatic substance derived from guaiacum or wood creosote and used chiefly as an expectorant, a local anesthetic, and an antiseptic.
| Veterinary Dictionary: guaiacol |
An extract of tar used as an expectorant.
- g. glyceryl ether — see guaifenesin. Previously called glyceryl guaiacolate.
| Wikipedia: Guaiacol |
| Guaiacol[1] | |
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| IUPAC name |
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| Other names | o-Methoxyphenol; Methylcatechol[2] |
| Identifiers | |
| CAS number | [] |
| PubChem | |
| SMILES |
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| ChemSpider ID | |
| Properties | |
| Molecular formula | C7H8O2 |
| Molar mass | 124.14 g/mol |
| Density | 1.112 g/cm3, liquid 1.129 g/cm3, crystals |
| Melting point |
28 °C, 301 K, 82 °F |
| Boiling point |
204-206 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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. Roasted coffee also contains the compound, which contributes to the flavor of the coffee.[3]
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Preparation and derivatives
Guaiacol is obtained directly from beechwood tar. It is produced industrially from pyrocatechin by methylation with potash and potassium methyl sulfate, or from anisole by nitration, reduction of the resulting ortho-nitroanisole to 2-aminoanisole, which is then diazotized and boiled with water.[citation needed] In the laboratory, it can be synthesized by the di-methylation of catechol followed by selective mono-demethylation.[4]
- C6H4(OH)2 + 2 (CH3O)2SO2 → C6H4(OCH3)2 + 2 HO(CH3O)SO2
- C6H4(OCH3)2 + C2H5SNa → C6H4(OCH3)(OH)
Guaiacol carbonate is known as duotal, the phosphate as phosphatol, the phosphite as guaiaco-phosphal; phosphotal is a mixture of the phosphites of creosote phenols.[citation needed] The valerianic ester of guaiacol is known as geosote, the benzoic as benzosol, the salicylic as guaiacolsalol, while the glycerin ether appears as guaiamar.
Uses
Guaiacol is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is also used in the preparation of eugenol[5] and vanillin.[6] The related derivative, dimethoxybenzene or veratrole, is also used in medicine. In preparation of food by smoking, guaiacol is the main chemical responsible for the smoky taste, whereas syringol is responsible for the smoky aroma.
Because of its natural color changing abilities, it is sometimes used as an indicator solution in various experiments involving enzymes.
Toxicology
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This section requires expansion. |
References
- ^ Merck Index, 13th Edition, 4568.
- ^ Chemindustry list of synonyms for guaiacol
- ^ Dorfner, R; Ferge, T; Kettrup, A; Zimmermann, R; Yeretzian, C (Sep 2003). "Real-time monitoring of 4-vinylguaiacol, guaiacol, and phenol during coffee roasting by resonant laser ionization time-of-flight mass spectrometry". Journal of agricultural and food chemistry 51 (19): 5768–73. doi:. ISSN 0021-8561. PMID 12952431.
- ^ R. N. Mirrington and G. I. Feutrill (1988). "Orcinol Monomethyl Ether". Org. Synth.; Coll. Vol. 6: 859.
- ^ C. F. H. Allen and J. W. Gates, Jr. (1955). "o-Eugenol". Org. Synth.; Coll. Vol. 3: 418.
- ^ 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. pp. 812–825.
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