Naphthoquinone

Naphthoquinone
Naphthoquinone[1]
Identifiers
CAS number 130-15-4 YesY
ChEMBL CHEMBL55934 N
Jmol-3D images Image 1
Properties
Molecular formula C10H6O2
Molar mass 158.15 g/mol
Density 1.422 g/cm³
Melting point

126 °C

Boiling point

Begins to sublime at 100 °C

Solubility in water 0.09 g/L
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Naphthoquinone is a class of natural phenols based on the C6-C4 skeleton.

1,4-Naphthoquinone can be viewed as derivatives of naphthalene through the replacement of two hydrogen atoms by two ketone groups.

The name is also used generically for two other isomers:

Naturally occurring naphtoquinones

Contents

Properties

1,4-Naphthoquinone forms yellow triclinic crystals and has an odor similar to benzoquinone. It is sparingly soluble in cold water, slightly soluble in petroleum ether, and freely soluble in most polar organic solvents. In alkaline solutions it produces a reddish-brown color. Because of their aromatic stability, 1,4-naphthoquinone derivatives are known to possess anti-bacterial and anti-tumor properties.

Naphthoquinone forms the central chemical structure of many natural compounds, most notably the K vitamins.

Medicinal uses

Naphthoquinone derivatives have significant pharmacological properties. They are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic properties. Plants with naphthoquinone content are widely used in China and the countries of South America, where they are used to treat malignant and parasitic diseases.[2]

See also

References

  1. ^ Merck Index, 11th Edition, 6315.
  2. ^ Babula, P; Adam, V; Havel, L; Kizek, R (2007). "Naphthoquinones and their pharmacological properties". Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 56 (3): 114–20. PMID 17867522. 

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Look at other dictionaries:

  • Naphthoquinone — Naph tho*qui none, n. [Naphthalene + quinone.] (Chem.) A yellow crystalline substance, {C10H6O2}, analogous to quinone, obtained by oxidizing naphthalene with chromic acid. [1913 Webster] …   The Collaborative International Dictionary of English

  • naphthoquinone — naftochinonas statusas T sritis chemija formulė C₁₀H₆(=O)₂ atitikmenys: angl. naphthoquinone rus. нафтохинон ryšiai: sinonimas – naftalendionas …   Chemijos terminų aiškinamasis žodynas

  • naphthoquinone — noun Either of two isomers of polycyclic aromatic ketones derived from naphthalene …   Wiktionary

  • naphthoquinone — 1. A quinone derivative of naphthalene, reducible to naphthohydroquinone; 1,4 n. derivatives have vitamin K activity ( e.g., menaquinone). 2. A class of compounds containing the n. (1) structure. * * * naph·tho·qui·none also naph·tha·qui·none… …   Medical dictionary

  • naphthoquinone — naph·tho·quinone …   English syllables

  • naphthoquinone — noun a fat soluble vitamin that helps in the clotting of blood • Syn: ↑vitamin K, ↑antihemorrhagic factor • Hypernyms: ↑fat soluble vitamin • Hyponyms: ↑vitamin K1, ↑phylloquinone, ↑ …   Useful english dictionary

  • 1,2-Naphthoquinone — Other names o Naphthoquinone, β naphthoquinone …   Wikipedia

  • 5,8-Dihydroxy-1,4-naphthoquinone — 5,8 Dihydroxy 1,4 naphthoquinone …   Wikipedia

  • 1,2-naphthoquinone — noun An isomer of naphthoquinone …   Wiktionary

  • 1,4-naphthoquinone — noun An isomer of naphthoquinone …   Wiktionary


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