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1,2-Naphthoquinone

Names
Preferred IUPAC name Naphthalene-1,2-dione
Other names o-Naphthoquinone, β-naphthoquinone
Identifiers
CAS Number	524-42-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34055
ChEMBL	ChEMBL52347
ChemSpider	10217
ECHA InfoCard	100.007.602
KEGG	C14783
PubChem CID	10667
UNII	804K62F61Q
CompTox Dashboard (EPA)	DTXSID2060171
InChI InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6HKey: KETQAJRQOHHATG-UHFFFAOYSA-N InChI=1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6HKey: KETQAJRQOHHATG-UHFFFAOYAZ
SMILES O=C1c2ccccc2\C=C/C1=O
Properties
Chemical formula	C10H6O2
Molar mass	158.156 g·mol
Appearance	yellow solid
Melting point	145 to 147 °C (293 to 297 °F; 418 to 420 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C
₁₀H
₆O
₂. This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride.

Occurrence

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

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.

See also

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

References

1. Louis F. Fieser (1937). "1,2-Naphthoquinone". Org. Synth. 17: 68. doi:10.15227/orgsyn.017.0068.
2. Yoshito Kumagai; Yasuhiro Shinkai; Takashi Miura; Arthur K. Cho (2011). "The Chemical Biology of Naphthoquinones and Its Environmental Implications". Annual Review of Pharmacology and Toxicology. 52: 221–47. doi:10.1146/annurev-pharmtox-010611-134517. PMID 21942631.
3. Qian, W.; Shichi, H. (2001). "Naphthoquinone-Induced Cataract in Mice: Possible Involvement of Ca 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". 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.

• 1,2-Naphthoquinones