1,2-Naphthoquinone

1,2-Naphthoquinone

Names
Other names o-Naphthoquinone, β-naphthoquinone
Identifiers
CAS Number	524-42-5 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL52347 Y
ChemSpider	10217 Y
ECHA InfoCard	100.007.602
KEGG	C14783 Y
PubChem	10667
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
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).
Y verify (what is YN ?)
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

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.