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Chemical Compound Review

CTK1E4199     1-(phenylhydrazinylidene) naphthalen-2-one

Synonyms: KSC244C9T, AC1NS5NF, 51383_FLUKA, 103624_SIAL, 52882-77-6, ...
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Disease relevance of Stearix Orange


Psychiatry related information on Stearix Orange


High impact information on Stearix Orange


Chemical compound and disease context of Stearix Orange


Biological context of Stearix Orange


Anatomical context of Stearix Orange

  • Horseradish peroxidase in the presence of hydrogen peroxide (HRP/H2O2) oxidizes a carcinogenic non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) to the ultimate carcinogen, which binds to calf thymus DNA [13].
  • SY7 was preferentially reduced in the skin cytosol of all species, whereas Sudan I was equally reduced in the skin cytosol and microsomal fractions [14].

Associations of Stearix Orange with other chemical compounds


Gene context of Stearix Orange

  • METHODS: High performance liquid chromatography (HPLC) with ultraviolet (UV) detection was employed for the separation of Sudan I metabolites formed by human recombinant CYPs and rat CYP1A1 [18].
  • Pretreatment of rats with beta-naphthoflavone or Sudan I, inducers of P450 1A1 and 1A2, and P450 1A1 alone, respectively, significantly stimulated the levels of 3-ABA-derived DNA adducts formed by rat liver microsomes [19].
  • Even though levels of CYP1A1 expression are low, <0.7% of total hepatic CYP, the CYP1A1 contribution to oxidation of carcinogenic Sudan I in the test set of human liver microsomes ranges from 12 to 30% [20].
  • From a small survey of 30 retail samples, 11 samples of crushed chilli, Italian pasta, chilli-snack and vegetable sauce contained levels of Sudan I ranging from 24 to 5591 microg kg(-1) [21].
  • Determination of 1-phenylazo-2-naphthol (Sudan I) in chilli powder and in chilli-containing food products by GPC clean-up and HPLC with LC/MS confirmation [21].

Analytical, diagnostic and therapeutic context of Stearix Orange

  • The potential of capillary liquid chromatography (microLC)-quadrupole/time-of-flight mass spectrometry (Q-TOF MS) for the confirmation of Sudan I, II, III and IV azo-dyes as contaminants in hot-chilli food products was demonstrated [22].
  • To study the genotoxic effects of Sudan I, the comet assay and micronucleus test (MNT) were used [1].


  1. Sudan I induces genotoxic effects and oxidative DNA damage in HepG2 cells. An, Y., Jiang, L., Cao, J., Geng, C., Zhong, L. Mutat. Res. (2007) [Pubmed]
  2. Pigmented contact dermatitis from azo dyes. I. Cross-sensitivity in humans. Kgzuka, T., Tashiro, M., Sano, S., Fujimoto, K., Nakamura, Y., Hashimoto, S., Nakaminami, G. Contact Derm. (1980) [Pubmed]
  3. Differential analysis of experimental hypermelanosis induced by UVB, PUVA, and allergic contact dermatitis using a brownish guinea pig model. Imokawa, G., Kawai, M., Mishima, Y., Motegi, I. Arch. Dermatol. Res. (1986) [Pubmed]
  4. The effect of time on the incidence of carcinomas obtained by the implantation of paraffin wax pellets into mouse bladder. Jull, J.W. Cancer Lett. (1979) [Pubmed]
  5. Electron microscope investigations on leishmaniasis in the Sudan. I. Morphometric studies on Leishmania amastigotes in various forms of human leishmaniasis. Veress, B., Abdalla, R.E., El Hassan, A.M. Ann. Trop. Med. Parasitol. (1980) [Pubmed]
  6. Epidemiology of nocturnal enuresis in a part of Khartoum, Sudan. I. The extensive study. Rahim, S.I., Cederblad, M. Acta paediatrica Scandinavica. (1986) [Pubmed]
  7. Sudan I is a potential carcinogen for humans: evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Stiborová, M., Martínek, V., Rýdlová, H., Hodek, P., Frei, E. Cancer Res. (2002) [Pubmed]
  8. Assay of Sudan I contamination of foodstuff by atmospheric pressure chemical ionization tandem mass spectrometry and isotope dilution. Di Donna, L., Maiuolo, L., Mazzotti, F., De Luca, D., Sindona, G. Anal. Chem. (2004) [Pubmed]
  9. The differential clastogenicity of Solvent Yellow 14 and FD & C Yellow No. 6 in vivo in the rodent micronucleus test (observations on species and tissue specificity). Westmoreland, C., Gatehouse, D.G. Carcinogenesis (1991) [Pubmed]
  10. Peroxidase-mediated reaction of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene with transfer ribonucleic acid. Stiborová, M., Frei, E., Klokow, K., Wiessler, M., Safarík, L., Anzenbacher, P., Hradec, J. Carcinogenesis (1990) [Pubmed]
  11. Variations on the standard protocol design of the hepatocyte DNA repair assay. Barfknecht, T.R., Naismith, R.W., Kornbrust, D.J. Cell Biol. Toxicol. (1987) [Pubmed]
  12. Oil-soluble dyes for marking Spodoptera frugiperda (Lepidoptera: Noctuidae). Vilarinho, E.C., Fernandes, O.A., Omoto, C., Hunt, T.E. J. Econ. Entomol. (2006) [Pubmed]
  13. Activation of carcinogens by peroxidase. Horseradish peroxidase-mediated formation of benzenediazonium ion from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) and its binding to DNA. Stiborová, M., Asfaw, B., Anzenbacher, P. FEBS Lett. (1988) [Pubmed]
  14. Reduction of azo dyes during in vitro percutaneous absorption. Collier, S.W., Storm, J.E., Bronaugh, R.L. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  15. Development and in-house validation of a liquid chromatography-electrospray-tandem mass spectrometry method for the simultaneous determination of Sudan I, Sudan II, Sudan III and Sudan IV in hot chilli products. Calbiani, F., Careri, M., Elviri, L., Mangia, A., Pistarà, L., Zagnoni, I. Journal of chromatography. A. (2004) [Pubmed]
  16. Determination of methyl yellow, Sudan I and Sudan II in water by high-performance liquid chromatography. Nagase, M., Osaki, Y., Matsueda, T. J. Chromatogr. (1989) [Pubmed]
  17. Evaluation of the rat micronucleus test with bone marrow and peripheral blood: summary of the 9th collaborative study by CSGMT/JEMS. MMS. Collaborative Study Group for the Micronucleus Test. Environmental Mutagen Society of Japan. Mammalian Mutagenicity Study Group. Wakata, A., Miyamae, Y., Sato, S., Suzuki, T., Morita, T., Asano, N., Awogi, T., Kondo, K., Hayashi, M. Environ. Mol. Mutagen. (1998) [Pubmed]
  18. Modulation of CYP1A1-mediated oxidation of carcinogenic azo dye Sudan I and its binding to DNA by cytochrome b5. Stiborova, M., Martinek, V., Schmeiser, H.H., Frei, E. Neuro Endocrinol. Lett. (2006) [Pubmed]
  19. 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2. Arlt, V.M., Hewer, A., Sorg, B.L., Schmeiser, H.H., Phillips, D.H., Stiborova, M. Chem. Res. Toxicol. (2004) [Pubmed]
  20. Expression of cytochrome P450 1A1 and its contribution to oxidation of a potential human carcinogen 1-phenylazo-2-naphthol (Sudan I) in human livers. Stiborová, M., Martínek, V., Rýdlová, H., Koblas, T., Hodek, P. Cancer Lett. (2005) [Pubmed]
  21. Determination of 1-phenylazo-2-naphthol (Sudan I) in chilli powder and in chilli-containing food products by GPC clean-up and HPLC with LC/MS confirmation. Mazzetti, M., Fascioli, R., Mazzoncini, I., Spinelli, G., Morelli, I., Bertoli, A. Food additives and contaminants. (2004) [Pubmed]
  22. Accurate mass measurements for the confirmation of Sudan azo-dyes in hot chilli products by capillary liquid chromatography-electrospray tandem quadrupole orthogonal-acceleration time of flight mass spectrometry. Calbiani, F., Careri, M., Elviri, L., Mangia, A., Zagnoni, I. Journal of chromatography. A. (2004) [Pubmed]
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