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The quinones are 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 archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14H
8O
2. Several isomers exist but these terms usually refer to 9,10-anthraquinone wherein the keto groups are located on the central ring. It is used as a digester additive to wood pulp for papermaking. Many anthraquinone derivatives are generated by organisms or synthesised industrially for use as dyes, pharmaceuticals, and catalysts. Anthraquinone is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.
In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups are substituted onto a benzene ring. These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene is commonly known as catechol, 1,3-dihydroxybenzene is commonly known as resorcinol, and 1,4-dihydroxybenzene is commonly known as hydroquinone.
1,2,4-Trihydroxyanthraquinone, commonly called purpurin, is an anthraquinone. It is a naturally occurring red/yellow dye. It is formally derived from 9,10-anthraquinone by replacement of three hydrogen atoms by hydroxyl (OH) groups.
Dantron (INN), also known as chrysazin or 1,8-dihydroxyanthraquinone, is an orange-colored organic substance. Many structurally-related compounds are known. In terms of its molecular structure, it is related anthraquinone by the replacement of two hydrogen atoms by hydroxyl groups (–OH). It is used in some countries as a stimulant laxative.
A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula (C12H53)(CO)2, formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes. The isomers may differ in the parent anthraquinone isomer and/or of the three hydroxyl groups.
1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin, is an organic compound with formula C
14H
8O
4 that occurs in the plant Rubia cordifolia. It is one of ten dihydroxyanthraquinone isomers. Its molecular structure can be viewed as being derived from anthraquinone by replacement of two hydrogen atoms (H) by hydroxyl groups (-OH).
1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts in the root of the madder plant, Rubia tinctorum.
A hydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).
A dihydroxynaphthoquinone is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms (H) by hydroxyl groups (OH).
Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring organic compound with formula C
10H
6O
4, formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.
Hydroxyquinone often refers to a hydroxybenzoquinone, any organic compound with formula C
6H
4O
3 which can be viewed as a derivative of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). When unqualified, the terms usually mean specifically the compound 2-hydroxy-1,4-benzoquinone, derived from 1,4-benzoquinone. That parent is sometimes simply called quinone, and this is the only hydroxy derivative of it.
In organic chemistry hydroxyanthraquinones refers to compounds with the formula C12H8-n(OH)n(CO)2 where n ≥ 1. Almost all hydroxyanthraquinones are derivative of 9,10-anthraquinone.
A tetrahydroxyanthraquinone, also called tetrahydroxyanthradione, is any of several isomeric organic compounds with formula (C12H44)(CO)2, almost invariably derived from 9,10-anthraquinone by replacing four hydrogen atoms by hydroxyl groups. Only a few of these isomers are commercially significant. These are 1,2,5,8-tetrahydroxyanthraquinone (quinalizarin), 1,4,5,8-tetrahydroxyanthraquinone, and 1,2,3,4-tetrahydroxyanthraquinone.
A hydroxybenzoquinone is any of several organic compounds that can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).
2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6H
4O
4, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid with planar molecules that exhibits ferroelectric properties.
1,4-Naphthoquinone or para-naphthoquinone is a quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.
1,2,4,5-Cyclohexanetetrol (also named cyclohexane-1,2,4,5-tetrol, 1,2,4,5-tetrahydroxycyclohexane, or para-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on two non-adjacent pairs of adjacent carbon atoms. Its formula can be written C
6H
12O
4, C
6H
8(OH)
4, or [–(CH(OH)–)2–CH
2–]2.
A dibromoanthracene is a derivative of anthracene with two bromine atoms. All compounds have the formula C14H8Br2. They are all isomers of one another.
1,5-Dihydroxyanthraquinone is an organic compound with the formula (C6H3OH)2(CO)2. It is one of several isomers of dihydroxyanthraquinone. An orange solid, it is a component of traditional Chinese medications. It serves as a chelating ligand for transition metals.
References
- 1 2 Wahl, Andre; Atack, F. W. (1919). The Manufacture Of Organic Dyestuffs. London: G. Bell And Sons, Limited. pp. 202–212.
- ↑ McGuigan, Hugh Alister (1921). An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. Philadelphia: P. Blakiston's son & Co. p. 132.
- ↑ Khalafy, Jabbar; Bruce, J.M. (2002-06-01). "Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones". Journal of Sciences, Islamic Republic of Iran. 13 (2). ISSN 1016-1104.
Silver(I) oxide in 1,4-dioxane converted 9,10-dihydroxy-1-oxo, 9,10-dihydroxy-1,5-dioxo, and 1,8-dioxo-1,2,3,4,5,6,7,8-octahydro anthracene into, respectively, 1-hydroxy-5,6,7,8-tetrahydro-, 1,5-dihydroxy-, and 1,8-dihydroxy-9,10-anthraquinone, in high yield.
- ↑ Thomson, Ronald Hunter (1971). Naturally Occurring Quinones . Academic Press. p. 66. ISBN 978-0-12-689650-3.
- ↑ Thomson, Ronald Hunter (1987). Naturally Occurring Quinones III: Recent Advances. Springer Netherlands. p. 358. ISBN 978-0-412-26730-7.
- ↑ Arcamone, Federico (1981). Doxorubicin: Anticancer Antibiotics. Academic Press. ISBN 978-0-12-059280-7.
- ↑ Ross Kelly, T. (1984). "Preface". Tetrahedron. 40 (22): 4537. doi:10.1016/S0040-4020(01)91512-1.
- ↑ Ashton, Richard E.; Andre, Pierre; Lowe, Nicholas J.; Whitefield, Martin (1983). "Anthralin: Historical and current perspectives". Journal of the American Academy of Dermatology. 9 (2): 173–192. doi:10.1016/s0190-9622(83)70125-8. PMID 6309924.
- ↑ Kemény, L.; Ruzicka, T.; Braun-Falco, O. (1990). "Dithranol: a review of the mechanism of action in the treatment of psoriasis vulgaris". Skin Pharmacology. 3 (1): 1–20. ISSN 1011-0283. PMID 2202336.
- 1 2 Buckingham, John B. (1996). Dictionary of Organic Compounds. Vol. 1. Chapman & Hall. ISBN 978-0-412-54090-5.