Naphthoquinones constitute a class of organic compounds structurally related to

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromat ...

. Two

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Is ...

s are common for the parent naphthoquinones: *

1,2-Naphthoquinone 1,2-Naphthoquinone or ''ortho''-naphthoquinone is a polycyclic aromatic organic compound with formula . This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with ferric chloride. Occurrence This diketone (an ortho- quinone ...

* 1,4-Naphthoquinone

Natural products

* Alkannin *

Hexahydroxy-1,4-naphthalenedione Spinochrome E, 2,3,5,6,7,8-Hexahydroxy-1,4-naphthalenedione, also called hexahydroxynaphthoquinone is a polyhydroxylated 1,4-naphthoquinones, pigments found in sea urchin shell ("test"), spine, gonads, coelomic fluid, and eggs, of sea urchin com ...

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 *

Menatetrenone Menatetrenone (INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they ...

* 2-Methoxy-1,4-naphthoquinone, a compound found in ''

Impatiens ''Impatiens'' is a genus of more than 1,000 species of flowering plants, widely distributed throughout the Northern Hemisphere and the tropics. Together with the genus '' Hydrocera'' (one species), ''Impatiens'' make up the family Balsaminacea ...

'' species * Nigrosporin B *

2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione 2,3,5,6,8-Pentahydroxy-1,4-naphthalenedione, also called 2,3,5,6,8-pentahydroxy-1,4-naphthoquinone or spinochrome D, is an organic compound with formula , formally derived from 1,4-naphthoquinone through the replacement of five hydrogen atoms by ...

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 Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula . It is regarded as a toxin and it is genotoxic and mutagenic. Plumbagin is a yellow dye,2,3,5,7-Tetrahydroxy-1,4-naphthalenedione 2,3,5,7-Tetraahydroxy-1,4-naphthalenedione, also called 2,3,5,7-tetrahydroxynaphthoquinone or spinochrome B, is an organic compound with formula , formally derived from 1,4-naphthoquinone through the replacement of four hydrogen atoms by hydroxyl ...

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 (2-Methyl-1,4-naphthoquinone), a vitamin K mimic *

5,8-Dihydroxy-1,4-naphthoquinone Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurringThomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.Thomson R.H. ...

and

dihydroxynaphthoquinone A dihydroxynaphthoquinone (formula: ) is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms (H) by hydroxyl groups (OH). The unqualified term "dihydroxynaphthoquinone" usua ...

s *

Atovaquone Atovaquone, sold under the brand name Mepron, is an antimicrobial medication for the prevention and treatment of ''Pneumocystis jirovecii'' pneumonia (PCP). Atovaquone is a chemical compound that belongs to the class of naphthoquinones. Atova ...

Buparvaquone Buparvaquone is a naphthoquinone antiprotozoal drug related to atovaquone. It is a promising compound for the therapy and prophylaxis of all forms of theileriosis. Buparvaquone has been shown to have anti-leishmanial activity ''in vitro''. It can ...

, an antiprotozoal drug used in veterinary medicine * Diazonaphthoquinone, a diazo derivative of naphthoquinone *

, from the biodegradation of naphthalene.

References

{{Naphthoquinone pt:Naftoquinona

Natural products

Synthetic naphthoquinones

See also

References