1.0 2010-04-08 22:08:22 UTC 2025-11-18 23:14:50 UTC FDB009011 Beechwood, creosote (fagus spp.) Guajol or Guaiacol, also known as 2-hydroxyanisole or 2-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is a sweet, medicinal, and phenolic tasting compound. Guaiacol is found in the highest concentration within a few different foods, such as sesames, coffee, and white wines and in a lower concentration in peppermints. Guaiacol has also been detected, but not quantified in white mustards, peppers, red bell peppers, cherry tomato, turmerics. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. 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 (PMID: 16152729). Guaiacol is used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880, 16152729) Creosote, wood C7H8O2 124.139 124.052429498 2-methoxyphenol guaiacol 8021-39-4 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 belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 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 a guaiacol monomethoxybenzene phenols liquid 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 Specdb::CMs 2757 Specdb::CMs 27537 Specdb::CMs 27673 Specdb::CMs 29102 Specdb::CMs 29909 Specdb::CMs 32166 Specdb::CMs 38055 Specdb::CMs 99681 Specdb::CMs 99682 Specdb::CMs 99683 Specdb::CMs 99684 Specdb::CMs 99685 Specdb::CMs 154951 Specdb::NmrTwoD 1638 Specdb::MsMs 6313 Specdb::MsMs 6314 Specdb::MsMs 6315 Specdb::MsMs 7241 Specdb::MsMs 7242 Specdb::MsMs 7243 Specdb::MsMs 13913 Specdb::MsMs 13914 Specdb::MsMs 13915 Specdb::MsMs 1471303 Specdb::MsMs 2790824 Specdb::MsMs 2790825 Specdb::MsMs 2790826 Specdb::MsMs 2914277 Specdb::MsMs 2914278 Specdb::MsMs 2914279 Specdb::EiMs 1571 Specdb::MsIr 1245 Specdb::MsIr 1246 Specdb::MsIr 1247 Specdb::NmrOneD 1697 Specdb::NmrOneD 3995 Specdb::NmrOneD 4283 Specdb::NmrOneD 9262 Specdb::NmrOneD 9263 Specdb::NmrOneD 9264 Specdb::NmrOneD 9265 Specdb::NmrOneD 9266 Specdb::NmrOneD 9267 Specdb::NmrOneD 9268 Specdb::NmrOneD 9269 Specdb::NmrOneD 9270 Specdb::NmrOneD 9271 Specdb::NmrOneD 9272 Specdb::NmrOneD 9273 Specdb::NmrOneD 9274 Specdb::NmrOneD 9275 Specdb::NmrOneD 9276 Specdb::NmrOneD 9277 Specdb::NmrOneD 9278 Specdb::NmrOneD 9279 Specdb::NmrOneD 9280 Specdb::NmrOneD 9281 HMDB0001398 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823