Guaiacol

Title: Guaiacol
CAS Registry Number: 90-05-1
CAS Name: 2-Methoxyphenol
Additional Names: methylcatechol; o-hydroxyanisole; 1-hydroxy-2-methoxybenzene
Trademarks: Anastil (Eberth)
Molecular Formula: C7H8O2
Molecular Weight: 124.14
Percent Composition: C 67.73%, H 6.50%, O 25.78%
Literature References: Isolated from guaiac resin: Sobrero, Ann. 48, 19 (1843); from hardwood tar: McGinness et al., Tappi 43, 1027 (1960). Prepd by mercuric oxide oxidation of lignin: Lewis, Pearl, US 2433227 (1947 to Sulphite Prod.); by oxidation of anisole with trifluoroperoxyacetic acid: McClure, Williams, J. Org. Chem. 27, 627 (1962); from acetovanillone + ZnCl2: Read, US 3057927 (1962 to Ontario Res. Found.); from the diazonium salt of o-anisidine: Herbst, DE 1148236 (1963 to Hoechst). Toxicity data: Taylor et al., Toxicol. Appl. Pharmacol. 6, 378 (1964).
Properties: White or slightly yellow cryst mass or colorless to yellowish, very refractive liquid; characteristic odor. Darkens on exposure to air and light. d (crystals) 1.129; d (liq) ~1.112. Solidif 28°, but may remain liq for a long time even at a much lower temp. bp 204-206°; bp4 53-55°. One gram dissolves in 60-70 ml water, 1 ml glycerol; miscible with alcohol, chloroform, ether, oils, glacial acetic acid. Slightly sol in petr ether; sol in NaOH soln; with moderately concd KOH it forms a sparingly sol compd. Protect from light. LD50 orally in rats: 725 mg/kg (Taylor).
Boiling point: bp 204-206°; bp4 53-55°
Density: d (crystals) 1.129; d (liq) ~1.112
Toxicity data: LD50 orally in rats: 725 mg/kg (Taylor)
Derivative Type: Phenylacetate
CAS Registry Number: 4112-89-4
Trademarks: Gujaphenyl (DDD); Gunyl (Hogapharm)
Molecular Formula: C15H14O3
Molecular Weight: 242.27
Percent Composition: C 74.36%, H 5.82%, O 19.81%
Therap-Cat: Expectorant.
Therap-Cat-Vet: Expectorant.
Keywords: Expectorant.
Guaiacol Benzoate Guaiacol Carbonate Guaiacol Phosphate Guaiacol Valerate Guaiapate

Guaiacol[1]
Guaiacol.png Guaiacol 3D.png
Identifiers
CAS number 90-05-1 YesY
PubChem 460
ChemSpider 447 YesY
UNII 6JKA7MAH9C YesY
KEGG D00117 YesY
ChEBI CHEBI:28591 YesY
ChEMBL CHEMBL13766 YesY
Jmol-3D images Image 1
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; 82 °F; 301 K
Boiling point 204–206 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Guaiacol is a naturally occurring organic compound with the formula C6H4(OH)(OCH3), discovered by Ascanio Sobrero[citation needed]. Although it is biosynthesized by a variety of organisms,[3] this yellowish aromatic oil is usually 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. The compound contributes to the flavor of many compounds, e.g. roasted coffee.[4]