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 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 aromati ...

. 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. Iso ...

s 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 Boraginaceae, borage family ''Alkanna tinctoria'' that are found in the south of France. The dye is used as a food coloring, food colouring and in cosmetics. It is used ...

* 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 ''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 Balsaminaceae. ...

'' 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 bleedin ...

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 *

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 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. Atovaq ...

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 (disambiguation), theileriosis. Buparvaquone has been shown to have anti-leishmanial ...

, 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.

References

{{Naphthoquinone pt:Naftoquinona

Natural products

Synthetic naphthoquinones

See also

References