Naphthoquinone

Chemical structure of 1,4-naphthoquinone

Naphthoquinones constitute a class of organic compounds (quinones) structurally related to naphthalene. Two isomers are common for the parent naphthoquinones:

• 1,2-Naphthoquinone
• 1,4-Naphthoquinone ^[1]

Naphthoquione structures are found in some dyes ^[2] and natural products. ^[3]

Natural products

Chemical structure of juglone, a compound produced by black walnut trees.

• Alkannin
• Hexahydroxy-1,4-naphthalenedione
• Juglone
• Lapachol
• Lawsone
• Menatetrenone
• 2-Methoxy-1,4-naphthoquinone, a compound found in Impatiens species
• Nigrosporin B
• Phylloquinone
• Plumbagin
• Spinochrome B
• Spinochrome D
• Vitamin K and related compounds
  • Phylloquinone
  • Vitamin K2
  • Menadione (2-Methyl-1,4-naphthoquinone)

Synthetic naphthoquinones

• 5,8-Dihydroxy-1,4-naphthoquinone and dihydroxynaphthoquinones
• Atovaquone
• Buparvaquone, an antiprotozoal drug used in veterinary medicine
• Diazonaphthoquinone, a diazo derivative of naphthoquinone
• 1,2-Naphthoquinone, from the biodegradation of naphthalene.

See also

• Hydroxynaphthoquinones

References

1. Caldwell, Erica; Deloux, Laurent; Srebnik, Morris (2001-04-15), "1,4-Naphthoquinone", in John Wiley & Sons, Ltd (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn001, ISBN   978-0-471-93623-7 , retrieved 2025-10-30
2. Dulo, Benson; Phan, Kim; Githaiga, John; Raes, Katleen; De Meester, Steven (December 2021). "Natural Quinone Dyes: A Review on Structure, Extraction Techniques, Analysis and Application Potential". Waste and Biomass Valorization. 12 (12): 6339–6374. Bibcode:2021WBioV..12.6339D. doi:10.1007/s12649-021-01443-9. ISSN   1877-2641.
3. Ahmadi, Esmaeil Sheikh; Tajbakhsh, Amir; Iranshahy, Milad; Asili, Javad; Kretschmer, Nadine; Shakeri, Abolfazl; Sahebkar, Amirhossein (2020-12-28). "Naphthoquinone Derivatives Isolated from Plants: Recent Advances in Biological Activity". Mini-Reviews in Medicinal Chemistry. 20 (19): 2019–2035. doi:10.2174/1389557520666200818212020. PMID   32811411.