Introduction

A quinone is a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of CH= groups into C(=O) groups with any necessary rearrangement of double bonds," resulting in "a fully conjugated cyclic dione structure." The class includes some heterocyclic compounds. The prototypical member of the class are 1,4-benzoquinone or cyclohexadienedione, often called simply quinone (whence the name of the class). Other important examples are 1,2benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. (Quinones are conjugated but not aromatic). Quinones are electrophilic Michael acceptors stabilised by conjugation. Depending on the quinone and the site of reduction, reduction can either rearomatise the compound or break the conjugation. Conjugate addition nearly always breaks the conjugation.

1,2- benzoquinone

1,4- benzoquinone

1,4- naphthoquinone

9,10- anthraquinone

The term quinone is also used more generally for a large class of compounds formally derived from aromatic quinones through replacement of some hydrogen atoms by other atoms or radicals.

Chloranil

Lawsone

DDQ

Occurrence and uses

Production of hydrogen peroxide

A large scale industrial application of quinones is for the production of hydrogen peroxide. 2Alkylanthraquinones are hydrogenated to the corresponding hydroquinones (quinizarins), which then transfer H2 to oxygen: dihydroanthraquinone + O2 anthraquinone + H2O2

In this way, several billion kilograms of H2O2 are produced annually. Biochemistry

Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Phylloquinone is also known as Vitamin K1 as it is used by animals to help form certain proteins, which are involved in blood coagulation, bone formation, and other processes. A natural example of the oxidation of hydroquinone to quinone is in the spray of bombardier beetles; hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterrent in the animal world.

Medicinal Uses
Natural or synthetic quinones show a biological or pharmacological activity, and some of them show antitumoral activity. possess a number of biological properties, including some claims in herbal medicine. These applications include purgative (sennosdes), antimicrobacterial (rhein- and saprorthoquinone), anti-tumor (emodin and jugone), inhibition of PGE2 biosynthesis (arnebinone and arnebifuranone) and anti-cardiovascular disease (tanshinone).[3]

Dyes Many natural and artificial coloring substances (dyes and pigments) are quinone derivatives. They are second only to azo dyes in importance as dyestuffs, with particular emphasis on blue colors. Alizarin (2,3-dihydroxy-9,10-anthraquinone), extracted from the madder plant, was the first natural dye to be synthesized from coal tar.

Reagents in organic chemistry Benzoquinone is used in organic chemistry as an oxidizing agent. Stronger quinone oxidising agents exist; for instance: chloranil and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (also known as DDQ). Nomenclature of Quinones Quinones are commonly named with a prefix that indicates the parent aromatic hydrocarbon ("benzo-" for benzene, "naphtho-" for naphthalene, "anthra-" for anthracene, etc.) and the "-quinone" suffix. Infix multipliers "-di-", "-tri-", "-tetra-" (etc.) are used when there are 4, 6, 8 (etc.) carbonyls. The position of the carbonyl groups can be indicated before the prefix (as in "1,4,5,8-naphthodiquinone") or after it ("anthra-1,4-quinone").

9,10-Anthraquineone

Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C14H8O2. Several isomers are possible, each of which can be viewed as a quinone derivative. The term anthraquinone, however, almost invariably refers to one specific isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. For instance, it is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol.

Synthesis
9,10-Anthraquinone is obtained industrially by the oxidation of anthracene, a reaction that is localized at the central ring. Chromium(VI) is the typical oxidant. It is also prepared by the Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. The resulting o-benzoylbenzoic acid then undergoes cyclization, forming anthraquinone. This reaction is useful for producing substituted anthraquinones. The Diels-Alder reaction of naphthoquinone and butadiene followed by oxidative dehydrogenation will also produce 9,10-anthraquinone. In a classic (1905) organic reaction called the Bally-Scholl synthesis, named after Oscar Bally and Roland Scholl, anthraquinone condenses with glycerol forming benzanthrone. 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.

Applications and natural occurrence

Dyestuff precursor
Synthetic dyes are often derived from 9,10-anthraquinone, such as alizarin. Important derivatives are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the

dinitroanthraquinone. Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and some insects.

Medicine
Derivatives of 9,10-anthraquinone include many important drugs (collectively called anthracenediones). They include Laxatives such as dantron, emodin, and aloe emodin, and some of the senna glycosides Antimalarials such as rufigallol Antineoplastics used in the treatment of cancer, such as mitoxantrone, pixantrone, and the anthracyclines.

Aloe emodin

Mitoxantrone

Pixantrone

Niche uses
9,10-Anthraquinone is used as a bird repellant on seeds and as a gas generator in satellite balloons. Natural anthraquinone derivatives tend to have laxative effects. Prolonged use and
abuse leads to melanosis coli. 5 anthraquinones have been shown to inhibit the formation of Tau

aggregates and dissolve paired helical filaments thought to be critical to Alzheimer's disease progression in both mouse models and in vitro testing but have not been investigated as a therapeutic agent.

Other isomers
Several other isomers of anthraquinone are possible, including the 1,2-, 1,4-, and 2,6anthraquinones. They are of comparatively minor importance. The term is also used in the more general sense of any compound that can be viewed as an anthraquinone with some hydrogen atoms replaced by other atoms or functional groups. These derivatives include substances that are technically useful or play important roles in living beings. Metabolism in humans The enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates including anthraquinones.[12] Benzoquinone is a quinone with a single benzene ring, of which there are only two: 1,4-Benzoquinone, most commonly (also para-benzoquinone, p-benzoquinone, paraquinone, or just quinone) 1,2-Benzoquinone, less commonly (also ortho-benzoquinone, o-benzoquinone, orthoquinone)