Anthraquinone

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Anthraquinone
IUPAC name Anthraquinone
Other names 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, Hoelite, Morkit, Corbit
Identifiers
3D model (JSmol)
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Properties
C14H8O2
Molar mass 208.23 g/mol
Appearance yellow or light gray to gray-green solid
Melting point
Boiling point
Hazards
R-phrases R36/37/38
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Anthraquinone (9,10-dioxoanthracene) is an aromatic organic compound. It is a derivative of anthracene. It has the appearance of yellow or light gray to gray-green solid crystalline powder.

Its other names are 9,10-anthracenedione, anthradione, 9,10-anthrachinon, anthracene-9,10-quinone, 9,10-dihydro-9,10-dioxoanthracene, and trade names Hoelite, Morkit, Corbit, and others.

Physical properties

It is insoluble in water but dissolves in alcohol, nitrobenzene and aniline. It is chemically fairly stable under normal conditions.

Natural occurrences

Anthraquinone naturally occurs in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where it serves as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.

Chemistry

There are several ways to obtain anthraquinone:

In a classic organic reaction called the Bally-Scholl synthesis (1905), anthraquinone condenses with glycerol forming benzanthrone[1]. In this reaction the quinone is first reduced with copper metal in sulfuric acid (converting one ketone group into a methylene group) after which the glycerol is added.

Industrial applications

Anthraquinone is used in production of dyes, such as alizarin. Many natural pigments are derivatives of anthraquinone. Anthraquinone is also used as a catalyst in production of wood pulp in pulp and paper industry. Another use is as a bird repellant on seeds.

A derivative of anthraquinone (2-ethylanthraquinone) is used to produce hydrogen peroxide commercially.

Medical uses

Anthraquinone is used as a laxative. Prolonged use and abuse leads to melanosis coli.[2][3]

External links

References

  1. L. C. Macleod and C. F. H. Allen (1943). "Benzathrone". Org. Synth.; Coll. Vol. 2: 62. 
  2. Müller-Lissner SA (1993). "Adverse effects of laxatives: fact and fiction". Pharmacology. 47 Suppl 1: 138–45. PMID 8234421.
  3. 3280173

de:Anthrachinon it:Antrachinone no:Antraquinoner sk:Antrachinón fi:Antrakinoni uk:Антрахінон


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