1,2-Naphthoquinone

changed 477204561 1,2-Naphthoquinone 1,2-naphthoquinone.svg 200px 1,2-Naphthoquinone Naphthalene-1,2-dione o-Naphthoquinone, β-naphthoquinone O=C1c2ccccc2\C=C/C1=O correct chemspider 10217 10667 correct kegg C14783 1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H KETQAJRQOHHATG-UHFFFAOYAZ 34055 correct EBI 52347 correct chemspider 1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H correct chemspider KETQAJRQOHHATG-UHFFFAOYSA-N correct CAS 524-42-5 correct FDA 804K62F61Q 10 6 2 yellow solid 145 to 147 1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C 10 H 6 O 2. It is classified as a 1,2-diketone as well as an ortho-quinone. More specifically, it is one of several naphthoquinones. Grolig, J. Wagner, R. Naphthoquinones 10.1002/14356007.a17_067 Preparation and occurrence 1,2-Naphthoquinone is produced commercially by air-oxidation of 1-naphthol in the presence of copper catalyst. A laboratory route involved oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.Louis F. Fieser Org. Synth. 1937 1,2-Naphthoquinone 17 68 10.15227/orgsyn.017.0068 free It is a metabolite of naphthalene. It arises from the naphthalene-1,2-oxide.Annual Review of Pharmacology and Toxicology 2011 The Chemical Biology of Naphthoquinones and Its Environmental Implications Yoshito Kumagai Yasuhiro Shinkai Takashi Miura Arthur K. Cho Arthur K. Cho 52 10.1146/annurev-pharmtox-010611-134517 221–47 21942631 It is also found in diesel exhaust particles. The accumulation of 1,2-naphthoquinone has been shown to damage the eyes of rats.Qian, W. Shichi, H. Naphthoquinone-Induced Cataract in Mice: Possible Involvement of Ca2+ Release and Calpain Activation Journal of Ocular Pharmacology and Therapeutics 17 4 383–392 2001 11572469 10.1089/108076801753162799 See also 1,4-Naphthoquinone, an isomer of 1,2-naphthoquinone Diazonaphthoquinone, a diazo derivative of 1,2-naphthoquinone References External links Troester, M. A. Lindstrom, A. B. Waidyanatha, S. Kupper, L. L. Rappaport, S. M. Stability of Hemoglobin and Albumin Adducts of Naphthalene Oxide, 1,2-Naphthoquinone, and 1,4-Naphthoquinone Toxicological Sciences 2002 68 2 314–321 12151627 10.1093/toxsci/68.2.314 free Kikuno, S. Taguchi, K. Iwamoto, N. 1,2-Naphthoquinone Activates Vanilloid Receptor 1 through Increased Protein Tyrosine Phosphorylation, Leading to Contraction of Guinea Pig Trachea Toxicology and Applied Pharmacology 2006 210 1–2 47–54 16039679 10.1016/j.taap.2005.06.015 etal Category:1,2-Naphthoquinones