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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 456362167 |
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| verifiedrevid = 477204561 |
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| Name = 1,2-Naphthoquinone |
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| Name = 1,2-Naphthoquinone |
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| ImageFile = 1,2-naphthoquinone.svg |
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| ImageFile = 1,2-naphthoquinone.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageName = 1,2-Naphthoquinone |
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| ImageName = 1,2-Naphthoquinone |
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| PIN = Naphthalene-1,2-dione |
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| OtherNames = ''o''-Naphthoquinone,<br /> β-naphthoquinone |
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| OtherNames = ''o''-Naphthoquinone,<br /> β-naphthoquinone |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| SMILES = O=C1c2ccccc2\C=C/C1=O |
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| SMILES = O=C1c2ccccc2\C=C/C1=O |
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| ChemSpider = 10217 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10217 |
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| ChemSpiderID = 10217 |
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| InChI = 1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H |
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| InChI = 1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H |
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| InChIKey = KETQAJRQOHHATG-UHFFFAOYAZ |
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| InChIKey = KETQAJRQOHHATG-UHFFFAOYAZ |
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| ChEBI = 34055 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 52347 |
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| ChEMBL = 52347 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 524-42-5 |
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| CASNo = 524-42-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 804K62F61Q |
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| RTECS = |
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| RTECS = |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=10|H=6|O=2 |
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| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>2</sub> |
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| MolarMass = |
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}} |
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| Appearance = yellow solid |
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| Density = |
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| MeltingPtC = 145 to 147 |
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| BoilingPt = |
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| Solubility = }} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''1,2-Naphthoquinone''' or '''''ortho''-naphthoquinone''' is a ] ] ] with formula {{chem|C|10|H|6|O|2}}. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ].<ref>{{cite journal|author=Louis F. Fieser|journal=Org. Synth. |year=1937|title=1,2-Naphthoquinone|volume=17|page=68|doi=10.15227/orgsyn.017.0068 |
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}}</ref> |
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==Occurrence== |
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This ] (an ortho-]) is a metabolite of ]. It arises from the ].<ref>{{cite journal|journal=Annual Review of Pharmacology and Toxicology|year=2011|title=The Chemical Biology of Naphthoquinones and Its Environmental Implications|author1=Yoshito Kumagai |author2=Yasuhiro Shinkai |author3=Takashi Miura |author4=Arthur K. Cho|author4-link=Arthur K. Cho|volume=52|doi=10.1146/annurev-pharmtox-010611-134517|pages=221–47|pmid=21942631}}</ref> |
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It is also found in diesel exhaust particles. The accumulation of this toxic metabolite in rats from doses of naphthalene has been shown to cause eye damage, including the formation of ]s.<ref>{{ cite journal |author1=Qian, W. |author2=Shichi, H. | title = Naphthoquinone-Induced Cataract in Mice: Possible Involvement of Ca{{sup|2+}} Release and Calpain Activation | journal = Journal of Ocular Pharmacology and Therapeutics | volume = 17 | issue = 4 | pages = 383–392 | year = 2001 | pmid = 11572469 | doi = 10.1089/108076801753162799 }}</ref> |
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== See also == |
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* ], an ] of 1,2-naphthoquinone |
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== References == |
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{{reflist}} |
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== External links == |
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* {{ cite journal |author1=Troester, M. A. |author2=Lindstrom, A. B. |author3=Waidyanatha, S. |author4=Kupper, L. L. |author5=Rappaport, S. M. | title = Stability of Hemoglobin and Albumin Adducts of Naphthalene Oxide, 1,2-Naphthoquinone, and 1,4-Naphthoquinone | journal = ] | year = 2002 | volume = 68 | issue = 2 | pages = 314–321 | pmid = 12151627 | doi = 10.1093/toxsci/68.2.314 | doi-access = free }} |
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* {{ cite journal |author1=Kikuno, S. |author2=Taguchi, K. |author3=Iwamoto, N. | title = 1,2-Naphthoquinone Activates Vanilloid Receptor 1 through Increased Protein Tyrosine Phosphorylation, Leading to Contraction of Guinea Pig Trachea | journal = ] | year = 2006 | volume = 210 | issue = 1–2 | pages = 47–54 | pmid = 16039679 | doi = 10.1016/j.taap.2005.06.015 |display-authors=etal}} |
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{{DEFAULTSORT:Naphthoquinone, 1, 2-}} |
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] |