The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Isonaphthol     naphthalen-2-ol

Synonyms: Betanaphthol, Hydronaphthol, beta-Naftol, beta-Naftolo, beta-Naphtol, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of C11713


High impact information on C11713

  • The 2-naphthol products are thought to derive from 6-endo-dig cyclization of (o-alkenyl)phenyl ketene intermediates, whereas 1-alkylidene-2-indanones are given from the 5-endo-dig cyclization pathway [2].
  • CYP2E1 and GSTM1 were significant determinants for urinary 2-naphthol concentrations in coke oven workers and GSTM1 and smoking were prognosticators among university students [3].
  • Urinary 1-OHP is a better indicator of occupational exposure to PAH in coke oven workers than 2-naphthol, whereas urinary 2-naphthol may be more sensitive for non-occupational inhalation exposure to PAH [3].
  • A simple colorimetric phenotyping assay, in conjunction with genotyping, was employed to demonstrate a significant correlation (r = 0.23, P < 0.01) of SULT1A1 genotype and platelet sulfotransferase activity towards 2-naphthol, a marker substrate for this enzyme [4].
  • 2. Maximal activity against benzoyl-DL-phenylalanine 2-naphthol ester and azo-casein was in the range pH 7.5-8 [5].

Biological context of C11713


Anatomical context of C11713


Associations of C11713 with other chemical compounds


Gene context of C11713

  • The role of the side-chain in O-DMN sulphation was studied using a series of structurally related beta-naphthol compounds as substrates for SULT1A1 and SULT1E1 [19].
  • There was a good correlation between the phenotyping assay and radiochemical assays for both 2-naphthol sulfotransferase and p-nitrophenol sulfotransferase activity (r = 0.85 and 0.69, respectively) [20].
  • AST-RB1 efficiently catalyzed N-sulfonation of alicyclic, alkyl, and arylamines such as 4-phenyl-1,2,3, 6-tetrahydropyridine, 1-[(5-chloro-2-oxo-3(2H)-benzothiazolyl)acetyl]-piperazine, desipramine, and aniline, whereas its catalytic activities toward 2-naphthol and dehydroepiandrosterone (DHEA) were very low [21].
  • 5. Mice lacking mrp1 have significantly increased hepatic transcription of at least two other ATP-binding cassette transporters, as well as increased 2-naphthol sulfotransferase activity, presumably to compensate for the lack of mrp1 [22].
  • 2-Naphthol, which has been found to be less efficient with regard to displacement of chromatin, did not cause up-regulation, but a significant decrease in PP1/PP2A activity [23].

Analytical, diagnostic and therapeutic context of C11713

  • The mass-transfer coefficient (K) for a model solid-liquid system (beta-naphthol particles and water) in place of a system of plant cells and a liquid medium was proposed as an intensity index of hydrodynamic stress effects on plant cells in suspension cultures under various conditions in the bioreactor systems [24].
  • Residue analysis of beta-naphthoxyacetic acid and beta-naphthol on field-sprayed tomatoes by high-pressure liquid chromatography [25].
  • This paper describes a simple and more sensitive reversed-phase HPLC method for the quantification of phenol, 4-nitrophenol and beta-naphthol and some of their glucuronide and sulphate conjugates in aqueous solution and liver perfusate buffer [26].
  • Recoveries were 100-104% for 2-Cl-4-NA added to purified D&C Red No. 36, 100% for 2-naphthol, and 100-110% for 2,4-DNA; relative standard deviations were 0.8-3.4% [27].
  • An attempt was made to establish a method for the simultaneous determination of urinary concentrations of phenol, o-, p- and m-cresols, 1- and 2-naphthol and xylenol isomers by capillary gas chromatography [28].


  1. Lichenoid eruption due to colour developer. A new occupational hazard of automatic self-photographing machines. Kersey, P., Stevenson, C.J. Contact Derm. (1980) [Pubmed]
  2. Ruthenium-catalyzed cyclization of epoxide with a tethered alkyne: formation of ketene intermediates via oxygen transfer from epoxides to terminal alkynes. Madhushaw, R.J., Lin, M.Y., Sohel, S.M., Liu, R.S. J. Am. Chem. Soc. (2004) [Pubmed]
  3. Effects of occupation, lifestyle and genetic polymorphisms of CYP1A1, CYP2E1, GSTM1 and GSTT1 on urinary 1-hydroxypyrene and 2-naphthol concentrations. Nan, H.M., Kim, H., Lim, H.S., Choi, J.K., Kawamoto, T., Kang, J.W., Lee, C.H., Kim, Y.D., Kwon, E.H. Carcinogenesis (2001) [Pubmed]
  4. Relationship of phenol sulfotransferase activity (SULT1A1) genotype to sulfotransferase phenotype in platelet cytosol. Nowell, S., Ambrosone, C.B., Ozawa, S., MacLeod, S.L., Mrackova, G., Williams, S., Plaxco, J., Kadlubar, F.F., Lang, N.P. Pharmacogenetics (2000) [Pubmed]
  5. Human cathepsin G. Catalytic and immunological properties. Starkey, P.M., Barrett, A.J. Biochem. J. (1976) [Pubmed]
  6. Determining the binding capability of the mouse major urinary proteins using 2-naphthol as a fluorescent probe. Sartor, G., Pagani, R., Ferrari, E., Sorbi, R.T., Cavaggioni, A., Cavatorta, P., Spisni, A. Anal. Biochem. (2001) [Pubmed]
  7. Correlation of urinary 1-hydroxypyrene and 2-naphthol with total suspended particulates in ambient air in municipal middle-school students in Korea. Kang, J.W., Cho, S.H., Kim, H., Lee, C.H. Arch. Environ. Health (2002) [Pubmed]
  8. Characterization of sulphotransferase in human ileum and colon. Pacifici, G.M., Franchi, M., Giuliani, L. Pharmacology (1989) [Pubmed]
  9. Effects of genetic polymorphisms of CYP1A1, CYP2E1, GSTM1, and GSTT1 on the urinary levels of 1-hydroxypyrene and 2-naphthol in aircraft maintenance workers. Lee, C.Y., Lee, J.Y., Kang, J.W., Kim, H. Toxicol. Lett. (2001) [Pubmed]
  10. The distribution of UDP-glucuronosyltransferases in rat liver parenchymal and nonparenchymal cells. Oesch, F., Arand, M., Coughtrie, M.W., Burchell, B., Steinberg, P. Biochem. Pharmacol. (1992) [Pubmed]
  11. Human liver arylamine N-sulfotransferase activity. Thermostable phenol sulfotransferase catalyzes the N-sulfation of 2-naphthylamine. Hernández, J.S., Powers, S.P., Weinshilboum, R.M. Drug Metab. Dispos. (1991) [Pubmed]
  12. Trypsin-like activity in the vaginal epithelial cells of the rat. Havran, R.T., Oster, G. J. Histochem. Cytochem. (1977) [Pubmed]
  13. In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Cho, T.M., Rose, R.L., Hodgson, E. Drug Metab. Dispos. (2006) [Pubmed]
  14. Human gastrointestinal sulfotransferases: identification and distribution. Chen, G., Zhang, D., Jing, N., Yin, S., Falany, C.N., Radominska-Pandya, A. Toxicol. Appl. Pharmacol. (2003) [Pubmed]
  15. Supramolecular assemblies and redox modulation of pyromellitic diimide-based cyclophane via noncovalent interactions with naphthol. Kato, S., Matsumoto, T., Ideta, K., Shimasaki, T., Goto, K., Shinmyozu, T. J. Org. Chem. (2006) [Pubmed]
  16. Urinary biomarkers of exposure to jet fuel (JP-8). Serdar, B., Egeghy, P.P., Waidyanatha, S., Gibson, R., Rappaport, S.M. Environ. Health Perspect. (2003) [Pubmed]
  17. Characterization of azo reduction activity in a novel ascomycete yeast strain. Ramalho, P.A., Cardoso, M.H., Cavaco-Paulo, A., Ramalho, M.T. Appl. Environ. Microbiol. (2004) [Pubmed]
  18. Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens. Sarabia, S.F., Zhu, B.T., Kurosawa, T., Tohma, M., Liehr, J.G. Chem. Res. Toxicol. (1997) [Pubmed]
  19. Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Falany, C.N., Ström, P., Swedmark, S. British journal of clinical pharmacology. (2005) [Pubmed]
  20. A simple colorimetric assay for phenotyping the major human thermostable phenol sulfotransferase (SULT1A1) using platelet cytosols. Frame, L.T., Ozawa, S., Nowell, S.A., Chou, H.C., DeLongchamp, R.R., Doerge, D.R., Lang, N.P., Kadlubar, F.F. Drug Metab. Dispos. (2000) [Pubmed]
  21. Purification and characterization of two amine N-sulfotransferases, AST-RB1 (ST3A1) and AST-RB2 (ST2A8), from liver cytosols of male rabbits. Shiraga, T., Iwasaki, K., Hata, T., Yoshinari, K., Nagata, K., Yamazoe, Y., Ohno, Y. Arch. Biochem. Biophys. (1999) [Pubmed]
  22. Altered expression of sulfotransferases, glucuronosyltransferases and mrp transporters in FVB/mrp1-/- mice. Bain, L.J., Feldman, R.A. Xenobiotica (2003) [Pubmed]
  23. Mitotic aberrations induced by carbaryl reflect tyrosine kinase inhibition with coincident up-regulation of serine/threonine protein phosphatase activity: implications for coordination of karyokinesis and cytokinesis. Renglin, A., Härmälä-Brasken, A.S., Eriksson, J.E., Onfelt, A. Mutagenesis (1999) [Pubmed]
  24. Technological problems in cultivation of plant cells at high density. Reprinted from Biotechnology and Bioengineering, Vol. XXII, No. 6, Pages 1203-1218 (1981). Tanaka, H. Biotechnol. Bioeng. (2000) [Pubmed]
  25. Residue analysis of beta-naphthoxyacetic acid and beta-naphthol on field-sprayed tomatoes by high-pressure liquid chromatography. Archer, T.E., Stokes, J.D. J. Agric. Food Chem. (1980) [Pubmed]
  26. High-performance liquid chromatographic determination of phenol, 4-nitrophenol, beta-naphthol and a number of their glucuronide and sulphate conjugates in organ perfusate. Thompson, M.J., Ballinger, L.N., Cross, S.E., Roberts, M.S. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  27. Liquid chromatographic determination of 2-chloro-4-nitroaniline, 2-naphthol, and 2,4-dinitroaniline in D&C red no. 36. Scher, A.L., Adamo, N.C. Journal of AOAC International. (1993) [Pubmed]
  28. Simultaneous determination of phenol, cresol, xylenol isomers and naphthols in urine by capillary gas chromatography. Bieniek, G. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
WikiGenes - Universities