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Chemical Compound Review

Resorcin     benzene-1,3-diol

Synonyms: Resorzin, Acnomel, Eskamel, Resorcine, Resorcino, ...
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Disease relevance of resorcinol

  • Histological examination after sacrifice at wk 52 revealed that the incidences of tongue papillomas and esophageal squamous cell carcinomas in the groups given MNAN followed by catechol (57.1% and 64.3%) or resorcinol (50% and 58.8%) were significantly higher than those in the carcinogen only controls (9.1, and 0%, respectively) [1].
  • The lower toxicity of monophenols and resorcinol as compared with that of di- and tri-phenols is due, in our opinion, to the fact that they are less oxidized under the conditions existing in the culture medium, and therefore do not produce sufficient levels of oxygen radicals [2].
  • Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure [3].
  • Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida [4].
  • Azoarcus anaerobius sp. nov., a resorcinol-degrading, strictly anaerobic, denitrifying bacterium [5].

Psychiatry related information on resorcinol


High impact information on resorcinol

  • Structurally dissimilar catechols (1,2-diphenols) and hydroquinones (1,4-diphenols) induce quinone reductase in these systems, but resorcinol (1,3-diphenol) and its substituted analogues are inactive [7].
  • Tunicamycin blocks incorporation of glucosamine label into practically all ganglioside species except for a resorcinol-positive, sialidase-sensitive band tentatively identified as GQ1b tetrasialoganglioside (Svennerholm ganglioside nomenclature) [8].
  • Selectivity for the beta 2-adrenoceptor was improved with tertiary branching at the gamma-carbon and further increased by aromatic substitution with resorcinol or saligenin [9].
  • Thin-layer chromatography of the isolated ganglioside fraction from T-cell lymphoblasts revealed two major resorcinol-positive bands [10].
  • Furthermore, using EPO-deficient mice and an EPO inhibitor resorcinol we demonstrate that eosinophil-derived peroxidase is critical in the development of GI dysfunction in experimental UC [11].

Chemical compound and disease context of resorcinol


Biological context of resorcinol


Anatomical context of resorcinol


Associations of resorcinol with other chemical compounds


Gene context of resorcinol

  • The enzymatic oxidation of resorcinol by lactoperoxidase was linked to inactivation since the same products were observed spectrally, albeit at a much lower level, as were observed with horseradish peroxidase [21].
  • The results are consistent with thyroid peroxidase- and lactoperoxidase-catalyzed oxidation of resorcinol derivatives to reactive radical species that covalently bind to amino acid residues unique to these two enzymes [21].
  • Concentrations of total serum N-acetyl-neuraminic acid (NANA) by high-performance liquid chromatography (HPLC) and lipid-bound sialic acid (LSA) by resorcinol procedure were evaluated and compared to carcinoembryonic antigen (CEA) as markers for colorectal carcinoma [28].
  • Fourteen novel CB2 receptor selective cannabinoids were synthesized via initial Lewis acid catalyzed rearrangement of resorcinol precursors to obtain the cannabinoid moiety [29].
  • The evidence for this mechanism includes irreversible, hydrogen peroxide-dependent loss of enzymatic activity by kinetics consistent with a suicide mechanism, concomitant with changes in the visible spectrum of the prosthetic heme group and covalent binding of resorcinol (ca. 10 mol/mol of lactoperoxidase inactivated) [21].

Analytical, diagnostic and therapeutic context of resorcinol


  1. Modification by catechol and resorcinol of upper digestive tract carcinogenesis in rats treated with methyl-N-amylnitrosamine. Yamaguchi, S., Hirose, M., Fukushima, S., Hasegawa, R., Ito, N. Cancer Res. (1989) [Pubmed]
  2. Comparative cytotoxicity of phenols in vitro. Passi, S., Picardo, M., Nazzaro-Porro, M. Biochem. J. (1987) [Pubmed]
  3. Suppression of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells by chemopreventive agents with a resorcin-type structure. Mutoh, M., Takahashi, M., Fukuda, K., Matsushima-Hibiya, Y., Mutoh, H., Sugimura, T., Wakabayashi, K. Carcinogenesis (2000) [Pubmed]
  4. Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida. Chapman, P.J., Ribbons, D.W. J. Bacteriol. (1976) [Pubmed]
  5. Azoarcus anaerobius sp. nov., a resorcinol-degrading, strictly anaerobic, denitrifying bacterium. Springer, N., Ludwig, W., Philipp, B., Schink, B. Int. J. Syst. Bacteriol. (1998) [Pubmed]
  6. Determination of 4-aminophenol using the quartz crystal microbalance sensor. Karousos, N.G., Reddy, S.M. The Analyst. (2002) [Pubmed]
  7. On the mechanisms of induction of cancer-protective enzymes: a unifying proposal. Prochaska, H.J., De Long, M.J., Talalay, P. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  8. Tunicamycin blocks neuritogenesis and glucosamine labeling of gangliosides in developing cerebral neuron cultures. Yavin, E., Richter-Landsberg, C., Duksin, D., Yavin, Z. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  9. alpha- and beta-Adrenoceptor activities of norepinephrine analogues in isolated tissues of the rat. Drummer, O., Culvenor, A.J., Jarrott, B., Louis, W.J. Circ. Res. (1980) [Pubmed]
  10. Expression of GD3 ganglioside in childhood T-cell lymphoblastic malignancies. Merritt, W.D., Casper, J.T., Lauer, S.J., Reaman, G.H. Cancer Res. (1987) [Pubmed]
  11. Immunopathogenesis of experimental ulcerative colitis is mediated by eosinophil peroxidase. Forbes, E., Murase, T., Yang, M., Matthaei, K.I., Lee, J.J., Lee, N.A., Foster, P.S., Hogan, S.P. J. Immunol. (2004) [Pubmed]
  12. Metabolism of resorcinylic compounds by bacteria: new pathway for resorcinol catabolism in Azotobacter vinelandii. Groseclose, E.E., Ribbons, D.W. J. Bacteriol. (1981) [Pubmed]
  13. Genetic Characterization of the Resorcinol Catabolic Pathway in Corynebacterium glutamicum. Huang, Y., Zhao, K.X., Shen, X.H., Chaudhry, M.T., Jiang, C.Y., Liu, S.J. Appl. Environ. Microbiol. (2006) [Pubmed]
  14. Symptomatic caliceal diverticula treated with extraperitoneal laparoscopic marsupialization fulguration and gelatin resorcinol formaldehyde glue obliteration. Hoznek, A., Herard, A., Ogiez, N., Amsellem, D., Chopin, D.K., Abbou, C.C. J. Urol. (1998) [Pubmed]
  15. On the reaction mechanism of phenol hydroxylase. New information obtained by correlation of fluorescence and absorbance stopped flow studies. Maeda-Yorita, K., Massey, V. J. Biol. Chem. (1993) [Pubmed]
  16. Resveratrol is a peroxidase-mediated inactivator of COX-1 but not COX-2: a mechanistic approach to the design of COX-1 selective agents. Szewczuk, L.M., Forti, L., Stivala, L.A., Penning, T.M. J. Biol. Chem. (2004) [Pubmed]
  17. Involvement of glucokinase translocation in the mechanism by which resorcinol inhibits glycolysis in hepatocytes. Agius, L. Biochem. J. (1997) [Pubmed]
  18. Inhibition of rabbit muscle aldolase by phosphorylated aromatic compounds. Blonski, C., De Moissac, D., Périé, J., Sygusch, J. Biochem. J. (1997) [Pubmed]
  19. Quantitative colorimetric determination of urinary p-aminophenol with an automated analyzer. Van Bocxlaer, J.F., Clauwaert, K.M., Lambert, W.E., De Leenheer, A.P. Clin. Chem. (1997) [Pubmed]
  20. Elucidation of the biosynthetic pathway of the allelochemical sorgoleone using retrobiosynthetic NMR analysis. Dayan, F.E., Kagan, I.A., Rimando, A.M. J. Biol. Chem. (2003) [Pubmed]
  21. Mechanism-based inactivation of lactoperoxidase and thyroid peroxidase by resorcinol derivatives. Divi, R.L., Doerge, D.R. Biochemistry (1994) [Pubmed]
  22. Cytokine release and cytotoxicity in human keratinocytes and fibroblasts induced by phenols and sodium dodecyl sulfate. Newby, C.S., Barr, R.M., Greaves, M.W., Mallet, A.I. J. Invest. Dermatol. (2000) [Pubmed]
  23. Endogenous immune response to gangliosides in patients with confined prostate cancer. Ravindranath, M.H., Muthugounder, S., Presser, N., Ye, X., Brosman, S., Morton, D.L. Int. J. Cancer (2005) [Pubmed]
  24. Leptin enhances glycogen storage in hepatocytes by inhibition of phosphorylase and exerts an additive effect with insulin. Aiston, S., Agius, L. Diabetes (1999) [Pubmed]
  25. Catalysis of nitrosation in vitro and in vivo in rats by catechin and resorcinol and inhibition by chlorogenic acid. Pignatelli, B., Bereziat, J.C., Descotes, G., Bartsch, H. Carcinogenesis (1982) [Pubmed]
  26. Studies of the mechanism of phenol hydroxylase: effect of mutation of proline 364 to serine. Xu, D., Enroth, C., Lindqvist, Y., Ballou, D.P., Massey, V. Biochemistry (2002) [Pubmed]
  27. Early proliferative responses of forestomach and glandular stomach of rats treated with five different phenolic antioxidants. Shibata, M.A., Yamada, M., Hirose, M., Asakawa, E., Tatematsu, M., Ito, N. Carcinogenesis (1990) [Pubmed]
  28. Use and limitations of serum total and lipid-bound sialic acid concentrations as markers for colorectal cancer. Erbil, K.M., Jones, J.D., Klee, G.G. Cancer (1985) [Pubmed]
  29. Synthesis and pharmacology of 11-nor-1-methoxy-9-hydroxyhexahydrocannabinols and 11-nor-1-deoxy-9-hydroxyhexahydrocannabinols: new selective ligands for the cannabinoid CB2 receptor. Marriott, K.S., Huffman, J.W., Wiley, J.L., Martin, B.R. Bioorg. Med. Chem. (2006) [Pubmed]
  30. Resorcinol-induced hypothydroidism in a patient on chronic hemodialysis. Katin, M.J., Teehan, B.P., Sigler, M.H., Schleifer, C.R., Gilgere, G.S. Ann. Intern. Med. (1977) [Pubmed]
  31. Circulating gangliosides of breast-cancer patients. Wiesner, D.A., Sweeley, C.C. Int. J. Cancer (1995) [Pubmed]
  32. Involvement of phosphorylase kinase inhibition in the effect of resorcinol and proglycosyn on glycogen metabolism in the liver. Van Schaftingen, E. Eur. J. Biochem. (1995) [Pubmed]
  33. Transformation of chlororesorcinol by the hydrocarbonoclastic yeasts Candida maltosa, Candida tropicalis, and Trichosporon oivide. Kurtz, A.M., Crow, S.A. Curr. Microbiol. (1997) [Pubmed]
  34. Contact dermatitis due to resorcinol in a radiotherapy dye. Pecegueiro, M. Contact Derm. (1992) [Pubmed]
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