1,2-Naphthoquinone

1,2-Naphthoquinone

Names
Other names o-Naphthoquinone, β-naphthoquinone
Identifiers
CAS Number	524-42-5
ChEMBL	ChEMBL52347
ChemSpider	10217
Jmol interactive 3D	Image
KEGG	C14783
PubChem	10667
InChI InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H Key: KETQAJRQOHHATG-UHFFFAOYSA-N InChI=1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H Key: KETQAJRQOHHATG-UHFFFAOYAZ
SMILES O=C1c2ccccc2\C=C/C1=O
Properties
Chemical formula	C10H6O2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C
10H
6O
2.

This double ketone (quinone) is a reactive metabolite of naphthalene and is 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.^[1]

See also

• 1,4-Naphthoquinone, an isomer of 1,2-naphthoquinone
• 2,6-Naphthoquinone, another isomer

References

1. Qian, W.; Shichi, H. (2001). "Naphthoquinone-Induced Cataract in Mice: Possible Involvement of Ca²⁺ Release and Calpain Activation". Journal of Ocular Pharmacology and Therapeutics 17 (4): 383–392. doi:10.1089/108076801753162799. PMID 11572469.

External links

• Troester, M. A.; Lindstrom, A. B.; Waidyanatha, S.; Kupper, L. L.; Rappaport, S. M. (2002). "Stability of Hemoglobin and Albumin Adducts of Naphthalene Oxide, 1,2-Naphthoquinone, and 1,4-Naphthoquinone" (pdf). Toxicological Sciences 68 (2): 314–321. doi:10.1093/toxsci/68.2.314. PMID 12151627.
• Kikuno, S.; Taguchi, K.; Iwamoto, N.; et al. (2006). "1,2-Naphthoquinone Activates Vanilloid Receptor 1 through Increased Protein Tyrosine Phosphorylation, Leading to Contraction of Guinea Pig Trachea". Toxicology and Applied Pharmacology 210 (1–2): 47–54. doi:10.1016/j.taap.2005.06.015. PMID 16039679.