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Chemical Compound Review

guaiacol     2-methoxyphenol

Synonyms: Guajacol, Guajakol, Anastil, Creodon, Guaicol, ...
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Disease relevance of guaiacol

  • Endogenous peroxidase activity, measured in vitro by guaiacol oxidation, occurred in substantially higher amounts in the primary ovarian adenocarcinomas than in benign tumors and control ovaries and could be demonstrated within ovarian adenocarcinoma cells by electron microscopy [1].
  • When eosinophil peroxidase (EPO) was incubated with Staphylococcus aureus (staph) approximately 40% remained firmly bound to the bacteria as indicated by guaiacol assay [2].
  • Guaiacol -- a new compound in the treatment of gastro-oesophageal reflux [3]?
  • The presented work focuses on the characterization of the role of hydrogen peroxide (H2O2)-producing (NADH peroxidase) and H2O2-consuming peroxidase (guaiacol POD) in the apoplastic washing fluid (AWF) of leaves for early stages of Mn toxicity and genotypic differences in Mn tolerance of cowpea [4].
  • The mean TPO activity measured by guaiacol as well as triiodide assays was significantly increased in multinodular goiter, whereas a nonsignificant increment was observed in cold adenoma [5].

High impact information on guaiacol

  • In contrast to APX, the guaiacol-utilizing peroxidases, which participate in the synthesis and crosslinking of cell wall components as part of the defense response, are not inhibited by SA or INA [6].
  • The guaiacol assay failed to show a definite pattern of inheritance in two families with MPO-deficient subjects [7].
  • The resulting tritiated product, guaiacol, is readily extracted into toluene and quantified by scintillation counting [8].
  • After i.p. administration, CLO was eliminated unchanged in feces and as two components which were chromatographically identical to synthetic CLO analogues bearing a m-methoxy-p-hydroxyphenyl (guaiacol) moiety in place of one or the other of its phenyl rings [9].
  • The inactivation of the enzyme in the presence of SCN- and H2O2 is prevented by electron donors such as iodide or guaiacol [10].

Chemical compound and disease context of guaiacol


Biological context of guaiacol


Anatomical context of guaiacol


Associations of guaiacol with other chemical compounds


Gene context of guaiacol

  • Indeed, the MCG/EPO complex had significantly greater iodinating and bactericidal activity than the free enzyme when standardized to equal guaiacol units of peroxidase activity [27].
  • The SCN- normally present in human saliva will reduce observed reaction rates by simple competition kinetics in the ABTS, guaiacol and pyrogallol assays and will increase the rates observed when Cl- is used as a donor in NBS assay for MPO [28].
  • 2. TPO enzyme activity (guaiacol assay) of unlabelled TPO was decreased after treatment with EndoH but not with other glycosidases [29].
  • The holoprotein was purified to homogeneity, which displayed a blue color typical of laccases and oxidized canonical laccase substrates such as guaiacol and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonate) [30].
  • The catechol-O-methyltransferase (COMT) activity was measured in cytosolic and membrane fractions at 37 degrees C, giving values of 33 and 114 units/mg of protein, respectively (1 unit produces 1 nmol of guaiacol/h) [31].

Analytical, diagnostic and therapeutic context of guaiacol


  1. Estrogen receptor and peroxidase activity in epithelial ovarian carcinomas. Holt, J.A., Lyttle, C.R., Lorincz, M.A., Stern, S.D., Press, M.F., Herbst, A.L. J. Natl. Cancer Inst. (1981) [Pubmed]
  2. Arming of mononuclear phagocytes by eosinophil peroxidase bound to Staphylococcus aureus. Ramsey, P.G., Martin, T., Chi, E., Klebanoff, S.J. J. Immunol. (1982) [Pubmed]
  3. Guaiacol -- a new compound in the treatment of gastro-oesophageal reflux? Heatley, R.V., Evans, B.K., Rhodes, J., Atkinson, M. Gut (1982) [Pubmed]
  4. The role of hydrogen peroxide-producing and hydrogen peroxide-consuming peroxidases in the leaf apoplast of cowpea in manganese tolerance. Fecht-Christoffers, M.M., Führs, H., Braun, H.P., Horst, W.J. Plant Physiol. (2006) [Pubmed]
  5. Dissociation of thyrotropin-dependent enzyme activities, reduced iodide transport, and preserved iodide organification in nonfunctioning thyroid adenoma and multinodular goiter. Masini-Repiso, A.M., Cabanillas, A.M., Bonaterra, M., Coleoni, A.H. J. Clin. Endocrinol. Metab. (1994) [Pubmed]
  6. Inhibition of ascorbate peroxidase by salicylic acid and 2,6-dichloroisonicotinic acid, two inducers of plant defense responses. Durner, J., Klessig, D.F. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  7. New approaches to the detection of myeloperoxidase deficiency. Dri, P., Cramer, R., Soranzo, M.R., Comin, A., Miotti, V., Patriarca, P. Blood (1982) [Pubmed]
  8. Radiochemical detection of dihydrodiol dehydrogenase: distribution of the enzyme in male Sprague-Dawley rat tissues and its sensitivity to inhibition by indomethacin and 6-medroxyprogesterone acetate. Ivins, J.K., Penning, T.M. Cancer Res. (1987) [Pubmed]
  9. Biotransformation of the antiestrogen clomiphene to chemically reactive metabolites in the immature female rat. Ruenitz, P.C., Arrendale, R.F., George, G.D., Thompson, C.B., Mokler, C.M., Nanavati, N.T. Cancer Res. (1987) [Pubmed]
  10. Low catalytic turnover of horseradish peroxidase in thiocyanate oxidation. Evidence for concurrent inactivation by cyanide generated through one-electron oxidation of thiocyanate. Adak, S., Mazumdar, A., Banerjee, R.K. J. Biol. Chem. (1997) [Pubmed]
  11. Nitric oxide promotes strong cytotoxicity of phenolic compounds against Escherichia coli: the influence of antioxidant defenses. Urios, A., López-Gresa, M.P., González, M.C., Primo, J., Martínez, A., Herrera, G., Escudero, J.C., O'Connor, J.E., Blanco, M. Free Radic. Biol. Med. (2003) [Pubmed]
  12. Microbial catabolism of vanillate: decarboxylation to guaiacol. Crawford, R.L., Olson, P.P. Appl. Environ. Microbiol. (1978) [Pubmed]
  13. Occurrence of two different forms of protocatechuate 3,4-dioxygenase in a Moraxella sp. Sterjiades, R., Pelmont, J. Appl. Environ. Microbiol. (1989) [Pubmed]
  14. Peroxidase and coupling activities of thyroid peroxidase in benign and malignant thyroid tumor tissues. Takamatsu, J., Hosoya, T., Tsuji, M., Yamada, M., Murakami, Y., Sakane, S., Kuma, K., Ohsawa, N. Thyroid (1992) [Pubmed]
  15. Horseradish peroxidase-catalyzed two-electron oxidations. Oxidation of iodide, thioanisoles, and phenols at distinct sites. Harris, R.Z., Newmyer, S.L., Ortiz de Montellano, P.R. J. Biol. Chem. (1993) [Pubmed]
  16. Distribution of guaiacol peroxidase in human endometrium and endocervical epithelium during the menstrual cycle. Tsibris, J.C., Trujillo, Y.P., Fernandez, B.B., Bardawil, W.A., Kunigk, A., Spellacy, W.N. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  17. Directed molecular evolution of cytochrome c peroxidase. Iffland, A., Tafelmeyer, P., Saudan, C., Johnsson, K. Biochemistry (2000) [Pubmed]
  18. Oral administration of phenolic antidiarrheic ingredients prevents ovariectomy-induced bone loss. Moriguchi, N., Hinoi, E., Takarada, T., Matsushima, N., Uno, K., Yoneda, Y. Biochem. Pharmacol. (2007) [Pubmed]
  19. Anti-thyroid peroxidase antibody in patients with autoimmune thyroid disease: possible identity with anti-microsomal antibody. Portmann, L., Hamada, N., Heinrich, G., DeGroot, L.J. J. Clin. Endocrinol. Metab. (1985) [Pubmed]
  20. Properties of guaiacol peroxidase activities isolated from corn root plasma membranes. Mika, A., Lüthje, S. Plant Physiol. (2003) [Pubmed]
  21. Oxidation of guaiacol by myeloperoxidase: a two-electron-oxidized guaiacol transient species as a mediator of NADPH oxidation. Capeillère-Blandin, C. Biochem. J. (1998) [Pubmed]
  22. Subcellular structure of bovine thyroid gland. The localization of the peroxidase activity in bovine thyroid. De Wolf, M.J., Lagrou, A.R., Hilderson, H.J. Biochem. J. (1978) [Pubmed]
  23. Purification and properties of oestrogen-induced uterine peroxidase. McNabb, T., Jellinck, P.H. Biochem. J. (1975) [Pubmed]
  24. Mechanisms of ferulic acid conversions to vanillic acid and guaiacol by Rhodotorula rubra. Huang, Z., Dostal, L., Rosazza, J.P. J. Biol. Chem. (1993) [Pubmed]
  25. Chemical and kinetic evidence for an essential histidine residue in the electron transfer from aromatic donor to horseradish peroxidase compound I. Bhattacharyya, D.K., Bandyopadhyay, U., Banerjee, R.K. J. Biol. Chem. (1993) [Pubmed]
  26. Indoleamine 2,3-dioxygenase. Purification and some properties. Shimizu, T., Nomiyama, S., Hirata, F., Hayaishi, O. J. Biol. Chem. (1978) [Pubmed]
  27. Binding of eosinophil peroxidase to mast cell granules with retention of peroxidatic activity. Henderson, W.R., Jong, E.C., Klebanoff, S.J. J. Immunol. (1980) [Pubmed]
  28. Quantitative, standardized assays for determining the concentrations of bovine lactoperoxidase, human salivary peroxidase, and human myeloperoxidase. Pruitt, K.M., Kamau, D.N., Miller, K., Månsson-Rahemtulla, B., Rahemtulla, F. Anal. Biochem. (1990) [Pubmed]
  29. Analysis of carbohydrate residues on human thyroid peroxidase (TPO) and thyroglobulin (Tg) and effects of deglycosylation, reduction and unfolding on autoantibody binding. Kiso, Y., Furmaniak, J., Morteo, C., Smith, B.R. Autoimmunity (1992) [Pubmed]
  30. A hyperthermophilic laccase from Thermus thermophilus HB27. Miyazaki, K. Extremophiles (2005) [Pubmed]
  31. Expression of functional membrane-bound and soluble catechol-O-methyltransferase in Escherichia coli and a mammalian cell line. Malherbe, P., Bertocci, B., Caspers, P., Zürcher, G., Da Prada, M. J. Neurochem. (1992) [Pubmed]
  32. Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. Ohki, S., Ogino, N., Yamamoto, S., Hayaishi, O. J. Biol. Chem. (1979) [Pubmed]
  33. Roles of the enantioselective glutathione S-transferases in cleavage of beta-aryl ether. Masai, E., Ichimura, A., Sato, Y., Miyauchi, K., Katayama, Y., Fukuda, M. J. Bacteriol. (2003) [Pubmed]
  34. Biotreatment of tannin-rich beer-factory wastewater with white-rot basidiomycete Coriolopsis gallica monitored by pyrolysis/gas chromatography/mass spectrometry. Yagüe, S., Terrón, M.C., González, T., Zapico, E., Bocchini, P., Galletti, G.C., González, A.E. Rapid Commun. Mass Spectrom. (2000) [Pubmed]
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