1,2-Naphthoquinone

1,2-Naphthoquinone
1,2-Naphthoquinone
Names
Preferred IUPAC name
Naphthalene-1,2-dione
Other names
o-Naphthoquinone,
β-naphthoquinone
Identifiers
CAS Number
  • 524-42-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34055
ChEMBL
  • ChEMBL52347 checkY
ChemSpider
  • 10217 checkY
ECHA InfoCard 100.007.602 Edit this at Wikidata
KEGG
  • C14783 checkY
PubChem CID
  • 10667
UNII
  • 804K62F61Q checkY
CompTox Dashboard (EPA)
  • DTXSID2060171 Edit this at Wikidata
InChI
  • InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H checkY
    Key: KETQAJRQOHHATG-UHFFFAOYSA-N checkY
  • InChI=1/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
    Key: KETQAJRQOHHATG-UHFFFAOYAZ
  • O=C1c2ccccc2\C=C/C1=O
Properties
Chemical formula
 C10H6O2
Molar mass 158.156 g·mol−1
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Chemical compound

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.[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]

See also

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 Ca2+ Release and Calpain Activation". Journal of Ocular Pharmacology and Therapeutics. 17 (4): 383–392. doi:10.1089/108076801753162799. PMID 11572469.
  • 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.