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Chemical Compound Review

Oricinol     5-methylbenzene-1,3-diol

Synonyms: Orcinol, Orcin, ORCINOL-CPD, PubChem15386, SureCN68497, ...
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Disease relevance of resorcinol monohydrate

  • Metabolism of resorcinylic compounds by bacteria. Purification and properties of orcinol hydroxylase from Pseudomonas putida 01 [1].
  • Measurable quantities of gangliosides GM3 and in particular GD3 were shed by the melanoma cells we have tested as detected on thin-layer chromatograms (TLC) stained with orcinol [2].
  • Preparative thin-layer chromatograms of chloroform-methanol extracts of Borrelia burgdorferi (B31) sonicates showed four fractions (Rf values of 0.84, 0.81, 0.66 and 0.61) that stained with iodine vapors, orcinol, or phospray, suggesting the presence of lipid-, carbohydrate-, and phosphorus-containing compounds [3].
  • During intraperiplasmic growth of Bdellovibrio bacteriovorus 109J on Escherichia coli some 30 to 60% of the initial E. coli RNA-ribose disappeared as cell-associated orcinol-positive material [4].
  • Lipid extraction of adult O. volvulus worms using a chloroform/methanol/water mixture yielded 10 lipid fractions of which 8 were demonstrated by the orcinol reagent to be glycolipids [5].

Psychiatry related information on resorcinol monohydrate

  • There was an exception: even though both rutin and orcinol are detoxified via conjugation with GA, the feeding behavior of possums did not suggest competition for detoxification pathways [6].

High impact information on resorcinol monohydrate

  • Neutral glycosphingolipids were isolated from BMMC by extraction of 3 to 5 X 10(8) cells in chloroform/methanol (1/1, v/v) and chromatography on DEAE-Sephadex, and were analyzed by thin layer chromatography with orcinol staining [7].
  • The ratio of hydroxylase to oxidase activities of the enzyme is decreased by an increase in the temperature of incubation; at 60 degrees the reaction with orcinol is almost 50% uncoupled from hydroxylation [1].
  • Acetylpyruvate hydrolase, the terminal inducible enzyme of the pathway of orcinol catabolism in Pseudomonas putida, catalyzes the quantitative conversion of acetylpyruvate into acetate and pyruvate [8].
  • Using a functional genomics approach, we have identified and characterized two closely related cDNAs from a rose petal library that each encode a protein capable of methylating the penultimate and immediate precursors (orcinol and orcinol monomethyl ether, respectively) to give the final orcinol dimethyl ether product [9].
  • TLC-immunostain analysis, as well as orcinol staining of thin-layer chromatograms of gangliosides of unlabeled cells, revealed that GM3 also accumulates in a higher amount in migrating compared to nonmigrating epithelial cell cultures [10].

Chemical compound and disease context of resorcinol monohydrate

  • Bacterial metabolism of resorcinylic compounds: purification and properties of orcinol hydroxylase and resorcinol hydroxylase from Pseudomonas putida ORC [11].
  • Orciprenaline, which featured an orcinol system, had a long duration of action and was active by mouth; Boehringer marketed it both as an inhaler and as a syrup for the prophylaxis of bronchospasm [12].

Biological context of resorcinol monohydrate

  • Densitometric measurements after orcinol staining showed, at day 10 of gestation, the presence of mono-, tetra-, tri- and dihexosylceramide in decreasing quantities, as well as four unidentified spots [13].

Anatomical context of resorcinol monohydrate

  • From these data, we find it appropriate to recommend the use of the Lowry (or, alternatively, the Bio-Rad) protein assay, the total lipids assay, and the orcinol carbohydrate assay for reasonably accurate determinations of the protein and energy contents of human milk [14].

Associations of resorcinol monohydrate with other chemical compounds

  • Evidence was not obtained for the expression of resorcinol hydroxylase in strain O1OC; the activity of orcinol hydroxylase appears to be recruited for this hydroxylation reaction [15].
  • The triterpenoids in the triterpenoid phase were quantitated using orcinol sulfuric acid detecting their carbohydrate chains and by HPLC [16].
  • Urinary quinol and orcinol outputs as indices of voluntary intake of heather (Calluna vulgaris L. (Hull)) by sheep [17].
  • In this study, five current methods for nucleic acid quantification were compared: (i) UV absorbance spectroscopy at 260 nm, (ii) colorimetric reaction with orcinol reagent, (iii) colorimetric reaction based on diphenylamine, (iv) fluorescence detection with Hoechst 33258 reagent, and (v) fluorescence detection with thiazole orange reagent [18].
  • Although each protein catalyzes the NAD(P)H and O2-dependent hydroxylation of both orcinol and resorcinol, the efficiency of the transformations of the substrates by the two enzymes is radically different; furthermore resorcinol hydroxylase is much more versatile in the aromatic compounds it can utilize as substrates and effectors [11].

Gene context of resorcinol monohydrate

  • [reaction: see text] CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinol p-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time [19].
  • Resorcinols (pentadecylresorcinol, olivetol, orcinol and resorcinol) exhibit antioxidant properties in liposomal systems [20].

Analytical, diagnostic and therapeutic context of resorcinol monohydrate

  • The circular dichroism spectrum of orcinol hydroxylase is also altered in the presence of orcinol [1].
  • MAbs CP3-50C2, CP3-53C5, and CP3-53C8 did not react with any antigens on Western blots but did bind to at least 10 distinct glycolipid bands as determined by orcinol staining on thin-layer chromatograms of M. pneumoniae lipid extracts [21].
  • In order to get samples with theoretical different potencies, Hib-TT samples were stored at -20, 4, 25, 37 and 70 degrees C for 5 weeks and after they were evaluated by HPLC and Orcinol methods and for immunogenicity and bactericidal activity [22].
  • On paper chromatography it comigrates with a 250-nm absorbing, orcinol-positive material [23].
  • In the present study, we analysed the ganglioside composition of Rcho-1 cells by HPTLC orcinol/H2So4, TLC/ immunostaining and immunohistochemistry [24].


  1. Metabolism of resorcinylic compounds by bacteria. Purification and properties of orcinol hydroxylase from Pseudomonas putida 01. Ohta, Y., Higgins, I., Ribbons, D.W. J. Biol. Chem. (1975) [Pubmed]
  2. Ganglioside GD3 shedding by human malignant melanoma cells. Bernhard, H., Meyer zum Büschenfelde, K.H., Dippold, W.G. Int. J. Cancer (1989) [Pubmed]
  3. Nonprotein antigens of Borrelia burgdorferi. Wheeler, C.M., Garcia Monco, J.C., Benach, J.L., Golightly, M.G., Habicht, G.S., Steere, A.C. J. Infect. Dis. (1993) [Pubmed]
  4. Metabolism of RNA-ribose by Bdellovibrio bacteriovorus during intraperiplasmic growth on Escherichia coli. Hespell, R.B., Odelson, D.A. J. Bacteriol. (1978) [Pubmed]
  5. Glycolipid antigens of adult O. volvulus reactive with patients sera from onchocerciasis endemic areas in Cameroon. Lando, G., Asonganyi, T., Ngogang, J., Ngu, J.L. African journal of medicine and medical sciences. (1994) [Pubmed]
  6. Conflicting demands on detoxification pathways influence how common brushtail possums choose their diets. Marsh, K.J., Wallis, I.R., McLean, S., Sorensen, J.S., Foley, W.J. Ecology (2006) [Pubmed]
  7. Identification of the neutral glycosphingolipids of murine mast cells: expression of Forssman glycolipid by the serosal but not the bone marrow-derived subclass. Katz, H.R., Schwarting, G.A., LeBlanc, P.A., Austen, K.F., Stevens, R.L. J. Immunol. (1985) [Pubmed]
  8. Metabolism of resorcinylic compounds by bacteria. Purification and properties of acetylpyruvate hydrolase from Pseudomonas putida 01. Davey, J.F., Ribbons, D.W. J. Biol. Chem. (1975) [Pubmed]
  9. O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Lavid, N., Wang, J., Shalit, M., Guterman, I., Bar, E., Beuerle, T., Menda, N., Shafir, S., Zamir, D., Adam, Z., Vainstein, A., Weiss, D., Pichersky, E., Lewinsohn, E. Plant Physiol. (2002) [Pubmed]
  10. Gangliosides of migrating and nonmigrating corneal epithelium in organ and cell culture. Yang, Z., Zhao, Z., Panjwani, N. Invest. Ophthalmol. Vis. Sci. (1996) [Pubmed]
  11. Bacterial metabolism of resorcinylic compounds: purification and properties of orcinol hydroxylase and resorcinol hydroxylase from Pseudomonas putida ORC. Ohta, Y., Ribbons, D.W. Eur. J. Biochem. (1976) [Pubmed]
  12. Epinephrine analogues. Sneader, W. Drug News Perspect. (2001) [Pubmed]
  13. Developmental changes in neutral glycosphingolipids of mouse placenta. Svejcar, J., Ehrlich-Rogozinski, S., Riedel, D., Müthing, J., Sharon, N. Glycoconj. J. (1993) [Pubmed]
  14. Simple and rapid macronutrient analysis of human milk for individualized fortification: basis for improved nutritional management of very-low-birth-weight infants? Polberger, S., Lönnerdal, B. J. Pediatr. Gastroenterol. Nutr. (1993) [Pubmed]
  15. Metabolism of resorcinylic compounds by bacteria: alternative pathways for resorcinol catabolism in Pseudomonas putida. Chapman, P.J., Ribbons, D.W. J. Bacteriol. (1976) [Pubmed]
  16. Isolation and quantification of Quillaja saponaria Molina saponins and lipids in iscom-matrix and iscoms. Behboudi, S., Morein, B., Rönnberg, B. Vaccine (1995) [Pubmed]
  17. Urinary quinol and orcinol outputs as indices of voluntary intake of heather (Calluna vulgaris L. (Hull)) by sheep. Martin, A.K., Milne, J.A., Moberley, P. The Proceedings of the Nutrition Society. (1975) [Pubmed]
  18. Comparison of DNA and RNA quantification methods suitable for parameter estimation in metabolic modeling of microorganisms. De Mey, M., Lequeux, G., Maertens, J., De Maeseneire, S., Soetaert, W., Vandamme, E. Anal. Biochem. (2006) [Pubmed]
  19. Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities. Wang, P., Zhang, Z., Yu, B. J. Org. Chem. (2005) [Pubmed]
  20. Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olivetol, orcinol and resorcinol. Hładyszowski, J., Zubik, L., Kozubek, A. Free Radic. Res. (1998) [Pubmed]
  21. Biological activities of monoclonal antibodies to Mycoplasma pneumoniae membrane glycolipids. Chandler, D.K., Olson, L.D., Kenimer, J.G., Probst, P.G., Rottem, S., Grabowski, M.W., Barile, M.F. Infect. Immun. (1989) [Pubmed]
  22. Relationships among physico-chemical and biological tests for a synthetic Hib-TT conjugate vaccine. Cuervo, M.L., P??rez, L.R., Oviedo, M., Costa, L., Perdomo, V. Vaccine (2007) [Pubmed]
  23. Low molecular weight iron in guinea pig reticulocytes. Pollack, S., Campana, T., Weaver, J. Am. J. Hematol. (1985) [Pubmed]
  24. Ganglioside composition of the rat choriocarcinoma cell line, Rcho-1. Shirai, T., Itonori, S., Tai, T., Soares, M.J., Shiota, K., Ogawa, T. Glycoconj. J. (1996) [Pubmed]
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