1.02010-04-08 22:08:22 UTC2020-09-17 15:33:36 UTCFDB009011Beechwood, 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, woodC7H8O2124.139124.0524294982-methoxyphenolguaiacol8021-39-4COC1=C(O)C=CC=C1InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3LHGVFZTZFXWLCP-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.MethoxyphenolsOrganic compoundsBenzenoidsPhenolsMethoxyphenolsAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAlkyl aryl ethersAnisolesHydrocarbon derivativesMethoxybenzenesPhenoxy compounds1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAlkyl aryl etherAnisoleAromatic homomonocyclic compoundEtherHydrocarbon derivativeMethoxybenzeneMethoxyphenolMonocyclic benzene moietyOrganic oxygen compoundOrganooxygen compoundPhenol etherPhenoxy compounda guaiacolmonomethoxybenzenephenolsliquidlogp1.32logs-0.27solubility6.74e+01 g/llogp1.51pka_strongest_acidic9.98pka_strongest_basic-4.9iupac2-methoxyphenolaverage_mass124.139mono_mass124.052429498smilesCOC1=C(O)C=CC=C1formulaC7H8O2inchiInChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3inchikeyLHGVFZTZFXWLCP-UHFFFAOYSA-Npolar_surface_area29.46refractivity34.5polarizability12.69rotatable_bond_count1acceptor_count2donor_count1physiological_charge0formal_charge0Specdb::EiMs1571Specdb::NmrTwoD1638Specdb::MsIr1245Specdb::MsIr1246Specdb::MsIr1247Specdb::NmrOneD1697Specdb::NmrOneD3995Specdb::NmrOneD4283Specdb::NmrOneD9262Specdb::NmrOneD9263Specdb::NmrOneD9264Specdb::NmrOneD9265Specdb::NmrOneD9266Specdb::NmrOneD9267Specdb::NmrOneD9268Specdb::NmrOneD9269Specdb::NmrOneD9270Specdb::NmrOneD9271Specdb::NmrOneD9272Specdb::NmrOneD9273Specdb::NmrOneD9274Specdb::NmrOneD9275Specdb::NmrOneD9276Specdb::NmrOneD9277Specdb::NmrOneD9278Specdb::NmrOneD9279Specdb::NmrOneD9280Specdb::NmrOneD9281Specdb::CMs2757Specdb::CMs27537Specdb::CMs27673Specdb::CMs29102Specdb::CMs29909Specdb::CMs32166Specdb::CMs38055Specdb::CMs99681Specdb::CMs99682Specdb::CMs99683Specdb::CMs99684Specdb::CMs99685Specdb::CMs154951Specdb::MsMs6313Specdb::MsMs6314Specdb::MsMs6315Specdb::MsMs7241Specdb::MsMs7242Specdb::MsMs7243Specdb::MsMs13913Specdb::MsMs13914Specdb::MsMs13915Specdb::MsMs1471303Specdb::MsMs2790824Specdb::MsMs2790825Specdb::MsMs2790826Specdb::MsMs2914277Specdb::MsMs2914278Specdb::MsMs2914279AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823