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Naphthoquinones constitute a class of
organic compounds In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone


Natural products

*
Alkannin Alkannin is a natural dye that is obtained from the extracts of plants from the borage family ''Alkanna tinctoria'' that are found in the south of France. The dye is used as a food colouring and in cosmetics. It is used as a red-brown food additive ...
* Hexahydroxy-1,4-naphthalenedione *
Juglone Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is an organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble i ...
*
Lapachol Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree.Record, Samuel J.. "Lapachol" pages 17-19. In: ''Tropical Woods'' (1925). This tree is known botanically as ''Handroanthus impetiginosus'', but was formerly known ...
*
Lawsone Lawsone (2-hydroxy-1,4-naphthoquinone), also known as hennotannic acid, is a red-orange dye present in the leaves of the henna plant (''Lawsonia inermis''), for which it is named, as well as in the flower of water hyacinth ('' Eichhornia crassipe ...
* Menatetrenone * 2-Methoxy-1,4-naphthoquinone, a compound found in '' Impatiens'' species * Nigrosporin B * 2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione *
Phylloquinone Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement. It is on the World Health Organization's List of Essential Medicines. As a supplement it is used to treat certain bleeding ...
* Plumbagin * 2,3,5,7-Tetrahydroxy-1,4-naphthalenedione *
Vitamin K Vitamin K refers to structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-synthesis modification of certain proteins that are required for blood coagulation ...
and related compounds


Synthetic naphthoquinones

*
Menadione Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed ...
(2-Methyl-1,4-naphthoquinone), a vitamin K mimic * 5,8-Dihydroxy-1,4-naphthoquinone and dihydroxynaphthoquinones * Atovaquone * Buparvaquone, an antiprotozoal drug used in veterinary medicine *
Diazonaphthoquinone Diazonaphthoquinone (DNQ) is a diazo derivative of naphthoquinone. Upon exposure to light, DNQ converts to a derivative that is susceptible to etching. In this way, DNQ has become an important reagent in photoresist technology in the semiconduct ...
, a diazo derivative of naphthoquinone * 1,2-Naphthoquinone, from the biodegradation of naphthalene.


See also

* Hydroxynaphthoquinones


References

{{Naphthoquinone pt:Naftoquinona