1.0 2014-09-05 17:10:10 UTC 2026-05-14 19:09:00 UTC T3D4576 Guaiacol SmallMolecule Guaiacol belongs to the methoxyphenols, a subclass of phenols within the organic compounds. This benzenoid compound has the formula C7H8O2 and an average molecular weight of 124.14 g/mol. It is an exogenous solid at room temperature. Biologically, it is a plant metabolite and acts as an inhibitor of EC 1.1.1.25 (shikimate dehydrogenase). It also serves as an inhibitor or substrate for the protein targets Albumin (ALB), Carbonic anhydrase 2 (CA2), and Cytochrome c (CYCS). The compound is used medicinally as an expectorant and as a disinfectant. It is also used in the preparation of synthetic vanillin. Guaiacol is present in Polyethylene Terephthalate and is found in 39 recorded sources. These include building and construction materials such as tents, canopies, stairs, ramps, and floors; household cleaning and consumer products including bleaching agents, perfumes within soaps and detergents, and smoking requisites such as cigar cigarettes and non-electric simulated smoking devices; electrical and electronic equipment including amplifiers, antennas, conductive bodies, electric switches, and electric hearing aids; and food, food processing and cookware, including food contact materials, cellar tools, food preservation, molasses and treatment of molasses, and fermentation processes for beer. Recorded exposure routes include oral, inhalation, and touch. In a clinical context, guaiacol is a biomarker of cancer (PMC13407726). Synthetic Toxin Organic Compound Ether Drug Metabolite Synthetic Compound 1-Hydroxy-2-methoxybenzene 2-Hydroxyanisole 2-Methoxy-Phenol 2-methoxyphenol 2-Methoxyphenol Anastil Beechwood, creosote (fagus spp.) BEECHWOOD, CREOSOTE (FAGUS SPP.) Catechol monomethyl ether Creodon Creosote creosote Guaiacol (liquid) extra pure Guaiastil Guaicol Guaicolina Guajakol Guajol Guasol Guiacol Methoxyphenol Methylcatachol Methylcatechol O-Guaiacol O-Hydroxyanisole O-Methoxy-Phenol O-Methoxyphenol O-Methyl catechol Pyrocatechol monomethyl ether Pyroguaiac acid C7H8O2 124.139 124.052429498 2-methoxyphenol guaiacol 1990-05-01 COC1=C(O)C=CC=C1 InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3 LHGVFZTZFXWLCP-UHFFFAOYSA-N Organic compounds Benzenoids Phenols Methoxyphenols Methoxyphenols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Aromatic homomonocyclic compounds a guaiacol monomethoxybenzene phenols Detected and Not Quantified Exogenous Cytoplasm Extracellular Tyrosine Metabolism SMP0000006 Alkaptonuria SMP0000169 Hawkinsinuria SMP0000190 Tyrosinemia Type I SMP0000218 Disulfiram Action Pathway SMP0000429 Tyrosinemia, Transient, of the Newborn SMP0000494 Dopamine beta-Hydroxylase Deficiency SMP0000498 Monoamine Oxidase-A Deficiency (MAO-A) SMP0000533 Hawkinsinuria SMP0125590 Tyrosinemia Type I SMP0125591 Tyrosinemia, Transient, of the Newborn SMP0125592 Dopamine beta-Hydroxylase Deficiency SMP0125594 Monoamine Oxidase-A Deficiency (MAO-A) SMP0125595 Guaiacol Drug Metabolism Action Pathway SMP0144699 Solid White powder. melting_point 28 °C boiling_point 205°C (401°F) solubility 18.7 mg/mL at 15 °C logp 1.32 logp 1.32 ALOGPS logs -0.27 ALOGPS solubility 6.74e+01 g/l ALOGPS logp 1.51 ChemAxon pka_strongest_acidic 9.98 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxyphenol ChemAxon average_mass 124.139 ChemAxon mono_mass 124.052429498 ChemAxon smiles COC1=C(O)C=CC=C1 ChemAxon formula C7H8O2 ChemAxon inchi InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3 ChemAxon inchikey LHGVFZTZFXWLCP-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 34.5 ChemAxon polarizability 12.69 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon No indication of carcinogenicity to humans (not listed by IARC). Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation. Guaiacol is also used in the preparation of synthetic vanillin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72240ac768> DB11359 HMDB01398 460 447 C01502 28591 CPD-400 JZ3 Guaiacol 3003635 15215658 11334365 9732390 4344880 1964765 6420144 16152729 Halliwell, Barry B., and Henrik E. Poulsen (2006). Cigarette Smoke and Oxidative Stress. Berlin: Springer. BE0005805 BE0000530 BE0000322