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Dihydroxyanthraquinone
A dihydroxyanthraquinone is any of several isomeric organic compounds with formula , formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl oxygens (=O) of the underlying anthraquinone. Isomers From 9,10-anthraquinone The unqualified term "dihydroxyanthraquinone" usually means a hydroxy derivative of 9,10-anthraquinone. The dihydroxy-9,10-anthraquinone functional group occurs widely in natural products, and is an important feature of the anthracycline antitumour antibiotics. In particular, 1,8-Dihydroxy-9,10-anthraquinone is the precursor for the important topical antipsoriatic drug anthralin, 1,8-dihydroxy-9-anthrone, There are 28 ways of choosing two of the 8 possible hydrogens, but because of the four-fold symmetry of the 9,10-an ...
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1,4-Dihydroxyanthraquinone
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 (as a glycoside) in the root of the madder plant, ''Rubia tinctorum''. Production Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride: ] It can also be prepared less efficiently from phthalic anhydride and hydroquinone. Uses Quinizarin is an inexpensive dye that is used to colour gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with aniline derivatives ...
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1,2-Dihydroxyanthraquinone
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, Colour Index International, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the Rubia, madder genus.The primary madder species from which alizarin historically has been obtained is ''Rubia tinctorum''. See also In 1869, it became the first natural dye to be produced synthetically. Alizarin is the main ingredient for the manufacture of the madder Lake pigment, lake pigments known to painters as rose madder and Alizarin crimson (color), alizarin crimson. Alizarin in the most common usage of the term has a deep red color, but the term is also part of the name for several related non-red dyes, such as Alizarine Cyanine Green and Alizarine Brilliant Blue. A use of alizarin in modern times is as a staining agent in biological research because it stains fr ...
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Hydroxyanthraquinone
In organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ... 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. Quoted by Khalafy and Bruce. Quoted by Khalafy and Bruce. Isomers One peculiarity of the hydroxyanthraquinones is the relative obscurity of the monohydroxy derivatives. Most hydroxyanthraquinones have two or more hydroxy groups. Dihydroxy Dihydroxyanthraquinones have the formula . The dyes alizarin ( 1,2-Dihydroxyanthraquinone) and quinizarin are prominent examples. Trihydroxy Trihydroxyanthraquinones have the formula . 1,2,4-Trihydroxyanthraquinone, commonly called purpurin, is a naturally occurring red/yellow dye. Tetrahydroxy Tetrahy ...
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1,5-Dihydroxyanthraquinone
1,5-Dihydroxyanthraquinone is an organic compound with the formula . It is one of several isomers of dihydroxyanthraquinone A dihydroxyanthraquinone is any of several isomeric organic compounds with formula , formally derived from 9,10-anthraquinone by replacing two hydrogen atoms by hydroxyl groups. Dihyroxyantraquinones have been studied since the early 1900s, and in .... An orange solid, it is a component of traditional Chinese medications. It serves as a chelating ligand for transition metals. References {{DEFAULTSORT:Dihydroxyanthraquinone, 1,5- Dihydroxyanthraquinones ...
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1,8-Dihydroxyanthraquinone
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. It should not be confused with ondansetron, an unrelated drug that was marketed in South Africa under the trade name "Dantron". Medical uses In the USA, dantron is not used because it is considered to be a carcinogen. In the UK it is considered a possible carcinogen and so its use is restricted to patients who already have a diagnosis of terminal cancer. It is mainly used in palliative care to counteract the constipating effects of opioids. Its British Approved Name was danthron, but it has now been changed to "dantron", the recommended International Nonproprietary Name.
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1,3-Dihydroxyanthraquinone
1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin, is an organic compound with formula that occurs in the plant ''Rubia cordifolia'' (Indian madder). Padma S. Vankar, Rakhi Shanker, Debajit Mahanta and S.C. Tiwari (2008), ''Ecofriendly sonicator dyeing of cotton with ''Rubia cordifolia'' Linn. using biomordant''. Dyes and Pigments, Volume 76, Issue 1, Pages 207-212. 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). Xanthopurpurin occurs in small amounts (as a glycoside) in the root of the common madder plant, ''Rubia tinctorum'', together with alizarin, purpurin and other anthraquinone derivatives. Goverdina C. H. Derksen, Harm A. G. Niederländer and Teris A. van Beek (2002), ''Analysis of anthraquinones in ''Rubia tinctorum'' L. by liquid chromatography coupled with diode-array UV and mass spectrometric detect ...
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Trihydroxyanthraquinone
A trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula , formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes. Wahl, Andre; Atack, F. W (1919) ''The Manufacture Of Organic Dyestuffs''. G. Bell And Sons, LimitedOnline versionaccessed on 2010-01-22. Hugh Alister McGuigan (1921), ''An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry''. P. Blakiston's son, PhiladelphiaOnline versionat archive.org, accessed on 2010-01-30. The isomers may differ in the parent anthraquinone isomer and/or of the three hydroxyl groups. In general there are 56 ways of choosing three out of the 8 hydrogens. However, if the underlying core is symmetrical, some of these choices will give identical molecules. Isomers From 9,10-anthraquinone Due to the symmetry of the 9,10-anthraquinone core, there are only 14 isomers. CRC (1996 ...
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Hydroxyquinone
Hydroxyquinone often refers to a hydroxybenzoquinone, any organic compound with formula 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. More generally, the term may refer to any derivative of any quinone (such as 1,2-benzoquinone, 1,4-naphthoquinone or 9,10-anthraquinone), where any number ''n'' of hydrogens have been replaced by ''n'' hydroxyls. In this case the number ''n'' is indicated by a multiplier prefix (mono-, di-, tri-, etc.), and the parent quinone's name is used instead of just "quinone" — as in tetrahydroxy-1,4-benzoquinone. File:Tetrahydroxy-1,4-benzoquinone-2D-skeletal.png, Tetrahydroxy-1,4-benzoquinone File:Juglone.png, 5-Hydroxy-1,4-naphthoquinone(Juglone) Fil ...
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Hydroxybenzoquinone
A hydroxybenzoquinone (formula: ) 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). In general, the term may mean any benzoquinone derivative where any number ''n'' of hydrogens have been replaced by ''n'' hydroxyls, so that the formula is . In this case the number ''n'' (which is between 1 and 4) is indicated by a multiplier prefix (mono-, di-, tri-, tetra-, penta-, or hexa-). The unqualified term "hydroxybenzoquinone" usually means a derivative of 1,4-benzoquinone. Other hydroxy- compounds can be derived from the other isomer, namely 1,2-benzoquinone or ''ortho''-benzoquinone. The IUPAC nomenclature uses dihydrobenzenedione instead of "benzoquinone", with the necessary prefixes to indicate the positions of the carbonyl oxygens (=O) — as in 2,3-dihydroxy-1a,4a-dihydrobenzene-1,4-dione (= 2,3-dihydroxy-1,4-benzoquinone). The hydroxybenzoquinones (in the particular or t ...
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Hydroxynaphthoquinone
A hydroxynaphthoquinone (formula: ) 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). In general, the term may mean any naphthoquinone derivative where any number ''n'' of hydrogens have been replaced by ''n'' hydroxyls, so that the formula is . In this case the number ''n'' (which is between 1 and 6) is indicated by a multiplier prefix (mono-, di-, tri-, tetra-, penta-, or hexa-). The unqualified term "hydroxynaphthoquinone" usually means a derivative of 1,4-naphthoquinone. Other hydroxy- compounds can be derived from other isomers of the latter, such as 1,2-naphthoquinone and 2,6-naphthoquinone. The IUPAC nomenclature uses dihydronaphthalenedione instead of "naphthoquinone", with the necessary prefixes to indicate the positions of the carbonyl oxygens (=O) — as in 5,8-dihydroxy-1a,8a-dihydronaphthalene-1,4-dione (= 5,8-dihydroxy-1,4-naphthoquinone). The hydroxyna ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical property, chemical or physical property, physical properties. Two main forms of isomerism are structural isomerism, structural (or constitutional) isomerism, in which ''chemical bond, bonds'' between the atoms differ; and stereoisomerism (or spatial isomerism), in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different Isotopologue, isotopologues. The depth of analy ...
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