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Anthraquinone (9,10-dioxoanthracene) is an aromatic
Aromatic hydrocarbon

An aromatic hydrocarbon or arene is a hydrocarbon, of which the molecular structure incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds....
 organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
. It is a derivative of anthracene
Anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings derived from coal-tar or other residues of thermal pyrolysis....
. 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.

s semisoluble
Solubility

Solubility is often seen as a property of a substance; for instance the solubility of a solid substance usually refers to the concentration of the substance in a liquid that has reached equilibrium with the substance in solid phase ....
 in water
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
 but dissolves in alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
, nitrobenzene
Nitrobenzene

Nitrobenzene, also known as nitrobenzol or oil of mirbane, is an organic compound with the chemical formula Carbon6Hydrogen5NitrogenOxygen2....
 and aniline
Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
.






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Anthraquinone (9,10-dioxoanthracene) is an aromatic
Aromatic hydrocarbon

An aromatic hydrocarbon or arene is a hydrocarbon, of which the molecular structure incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds....
 organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
. It is a derivative of anthracene
Anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings derived from coal-tar or other residues of thermal pyrolysis....
. 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 semisoluble
Solubility

Solubility is often seen as a property of a substance; for instance the solubility of a solid substance usually refers to the concentration of the substance in a liquid that has reached equilibrium with the substance in solid phase ....
 in water
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
 but dissolves in alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
, nitrobenzene
Nitrobenzene

Nitrobenzene, also known as nitrobenzol or oil of mirbane, is an organic compound with the chemical formula Carbon6Hydrogen5NitrogenOxygen2....
 and aniline
Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
. It is chemically fairly stable under normal conditions.

Natural occurrences

Anthraquinones naturally occur in some plants (eg. aloe latex, senna, rhubarb
Rhubarb

Rheum is a genus of perennial plants that grows from thick short rhizomes. The genus is in the family Polygonaceae, and includes the vegetable rhubarb The plants have large leaf that are somewhat triangular shaped with long fleshy Petiole s....
, and Cascara buckthorn
Rhamnus purshiana

Rhamnus purshiana is a species of buckthorn native to western North America from southern British Columbia south to central California, and inland to western Montana....
), fungi, lichen
Lichen

Lichens are composite organisms consisting of a symbiosis association of a fungus with a Photosynthesis partner , usually either a green algae or Cyanobacteria ....
s, and insect
Insect

Insects are the biggest class of arthropods and the only ones with wings. They are the most diverse group of animals on the planet. They are most diverse at the equator and their diversity declines toward the poles....
s, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative
Laxative

Laxatives are foods, compounds, or drugs taken to induce bowel movements or to loosen the stool, most often taken to treat constipation. Certain stimulant, lubricant, and saline laxatives are used to evacuate the Colon for rectum and bowel examinations, and may be supplemented by enemas in that circumstance....
 effects.

Chemistry

There are several ways to obtain anthraquinone:
  • Oxidation of anthracene
    Anthracene

    Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings derived from coal-tar or other residues of thermal pyrolysis....
  • Condensation of benzene
    Benzene

    Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
     with phthalic anhydride
    Phthalic anhydride

    Phthalic anhydride is the organic compound with the chemical formula C6H42O. This anhydride of phthalic acid, a colourless solid, is an important industrial chemical, especially for the large-scale production of plasticizers for plastics....
     in presence of AlCl3 (Friedel-Crafts substitution
    Friedel-Crafts reaction

    The Friedel-Crafts reactions are a set of organic reaction developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel-Crafts reactions: alkylation reactions and acylation reactions....
    ). The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone.
  • Diels-Alder reaction
    Diels-Alder reaction

    The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
     (from naphthoquinone
    Naphthoquinone

    Naphthoquinone, or more precisely 1,4-naphthoquinone, is an organic compound. It forms yellow triclinic crystals and has an odor similar to benzoquinone....
     and a buta-1,3-diene followed by oxidation)
  • Retro-DA reaction: the Rickert-Alder reaction.


In a classic organic reaction
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 called the Bally-Scholl synthesis (1905), anthraquinone condenses
Condensation reaction

A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule....
 with glycerol
Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
 forming benzanthrone
Benzanthrone

Benzanthrone is an aromatic hydrocarbon derivate used as a dyestuff intermediate for anthraquinone-based dyes. It has the appearance of a light yellow to brown-green powder with melting point of 170 ?C....
. In this reaction the quinone is first reduced with copper
Copper

Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
 metal in sulfuric acid
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
 (converting one ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 group into a methylene
Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
 group) after which the glycerol is added.

Industrial applications

  • Anthraquinone is used in production of dyes, such as alizarin
    Alizarin

    Alizarin is an organic compound that is historically important as a prominent dye. It is an anthraquinone originally derived from the root of the madder plant....
    .
  • Many natural pigment
    Pigment

    A pigment is a material that changes the color of light it Reflection as the result of selective color absorption. This physical process differs from fluorescence, phosphorescence, and other forms of luminescence, in which the material itself emits light....
    s are derivatives of anthraquinone.
  • Anthraquinone may be used as a catalyst in production of chemical pulp by the Kraft
    Kraft process

    The kraft process describes a technology for conversion of wood into wood pulp consisting of almost pure cellulose fibers. The process entails treatment of wood chips with a mixture of sodium hydroxide and sodium sulfide that break the bonds that link lignin to the cellulose....
     or Soda-AQ process
    Soda pulping

    Soda pulping is a chemical process for making wood pulp with sodium hydroxide as cooking chemical. In the Soda-AQ process anthraquinone may be used as a pulping additive to decrease the carbohydrate degradation....
    es.
  • Another use is as a bird repellant on seeds.
  • A derivative of anthraquinone (2-ethylanthraquinone) is used to produce hydrogen peroxide
    Hydrogen peroxide

    Hydrogen peroxide is a very pale blue liquid which appears colorless in a dilute solution, slightly more viscous than water. It is a weak acid....
     commercially.


Medical uses

Anthraquinone is used as a laxative
Laxative

Laxatives are foods, compounds, or drugs taken to induce bowel movements or to loosen the stool, most often taken to treat constipation. Certain stimulant, lubricant, and saline laxatives are used to evacuate the Colon for rectum and bowel examinations, and may be supplemented by enemas in that circumstance....
. Prolonged use and abuse
Substance abuse

Substance abuse is the overindulgence in and dependence of a drug or other chemical leading to effects that are detrimental to the individual's physical and mental health, or the Quality of life of others....
 leads to melanosis coli
Melanosis coli

Melanosis coli is a disorder of pigmentation of the wall of the Colon , identified at the time of colonoscopy. It is benign, and has no significant correlation with disease....
.

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