“1,2-Naphthoquinone”的意思、由来-开放百科全书

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1,2-Naphthoquinone

释义

Occurrence
See also
References
External links

{{chembox
| Watchedfields = changed
| verifiedrevid = 477204561
| Name = 1,2-Naphthoquinone
| ImageFile = 1,2-naphthoquinone.svg
| ImageSize = 200px
| ImageName = 1,2-Naphthoquinone
| OtherNames = o-Naphthoquinone,
β-naphthoquinone
| Section1 = {{Chembox Identifiers
| SMILES = O=C1c2ccccc2\\C=C/C1=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10217
| PubChem = 10667
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14783
| InChI = 1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
| InChIKey = KETQAJRQOHHATG-UHFFFAOYAZ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 52347
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KETQAJRQOHHATG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 524-42-5
| RTECS =
|Section2={{Chembox Properties
|C=10|H=6|O=2
| MolarMass =
| Appearance = yellow solid
| Density =
| MeltingPtC = 145 to 147
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula {{chem|C|10|H|6|O|2}}. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.^[1]

Occurrence

This diketone (an ortho-quinone) is a metabolite of naphthalene. It arises from the naphthalene-1,2-oxide.^[2]

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 cataracts.^[3]

References

1. ^{{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}}
2. ^{{cite journal|journal=Annual Review of Pharmacology and Toxicology|year=2011|title=The Chemical Biology of Naphthoquinones and Its Environmental Implications|authors=Yoshito Kumagai, Yasuhiro Shinkai, Takashi Miura, Arthur K. Cho|volume=52|doi=10.1146/annurev-pharmtox-010611-134517|pages=221–47}}
3. ^{{ cite journal |author1=Qian, W. |author2=Shichi, H. | title = Naphthoquinone-Induced Cataract in Mice: Possible Involvement of Ca²⁺ 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 }}

External links

{{ 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 = Toxicological Sciences | year = 2002 | volume = 68 | issue = 2 | pages = 314–321 | pmid = 12151627 | doi = 10.1093/toxsci/68.2.314 | url = http://toxsci.oxfordjournals.org/content/68/2/314.full.pdf | format = pdf }}
{{ 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 = Toxicology and Applied Pharmacology | year = 2006 | volume = 210 | issue = 1–2 | pages = 47–54 | pmid = 16039679 | doi = 10.1016/j.taap.2005.06.015 | url = http://linkinghub.elsevier.com/retrieve/pii/S0041-008X(05)00380-7 |display-authors=etal}}

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Occurrence

See also

References

External links