1,2-Naphthoquinone

1,2-Naphthoquinone
1,2-Naphthoquinone
Names
Preferred IUPAC name
Naphthalene-1,2-dione
Other names
o-Naphthoquinone,
β-naphthoquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.602 Edit this at Wikidata
KEGG
UNII
  • 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
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).
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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.