1,2-Naphthoquinone

1,2-Naphthoquinone
Other names o-Naphthoquinone, β-naphthoquinone
Identifiers
CAS number	524-42-5 Y
PubChem	10667
ChemSpider	10217 Y
KEGG	C14783 Y
ChEMBL	CHEMBL52347 N
Jmol-3D images	Image 1
SMILES O=C1c2ccccc2\C=C/C1=O
InChI InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H Y Key: KETQAJRQOHHATG-UHFFFAOYSA-N Y InChI=1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H Key: KETQAJRQOHHATG-UHFFFAOYAZ
Properties
Molecular formula	C10H6O2
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

'1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C₁₀H₆O₂.

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 (August 2001). "Naphthoquinone-Induced cataract in mice: possible involvement of Ca²⁺ release and calpain activation". J Ocul Pharmacol Ther 17 (4): 383–92. doi:10.1089/108076801753162799. PMID 11572469. 

External links

• Troester MA, Lindstrom AB, Waidyanatha S, Kupper LL, Rappaport SM (August 2002). "Stability of hemoglobin and albumin adducts of naphthalene oxide, 1,2-naphthoquinone, and 1,4-naphthoquinone". Toxicol. Sci. 68 (2): 314–21. doi:10.1093/toxsci/68.2.314. PMID 12151627. http://toxsci.oxfordjournals.org/content/68/2/314.full. 
• Kikuno S, Taguchi K, Iwamoto N, et al. (January 2006). "1,2-Naphthoquinone activates vanilloid receptor 1 through increased protein tyrosine phosphorylation, leading to contraction of guinea pig trachea". Toxicol. Appl. Pharmacol. 210 (1–2): 47–54. doi:10.1016/j.taap.2005.06.015. PMID 16039679. http://linkinghub.elsevier.com/retrieve/pii/S0041-008X(05)00380-7. 
• Material Safety Data Sheet