Dihydroxyanthraquinones
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Dihydroxyanthraquinones
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-anth ...
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1,2-Dihydroxyanthraquinone
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the 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 pigments known to painters as rose madder and 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 notable use of alizarin in modern times is as a staining agent in biological research because it stains free calcium and certain calcium compounds a red or light ...
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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 detec ...
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1,8-Dihydroxyanthraquinone
Dantron (INN), also known as chrysazin or 1,8-dihydroxyanthraquinone, is an organic substance, formally derived from 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.British National Formulary web ...
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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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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 or ''para''-benzoquinone (which often called just "quinone"). 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) File:Alizarin chemical structure.png, 1, ...
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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 ...
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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 hydroxy ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''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 isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-for ...
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1,2-anthraquinone
Onekama ( ) is a village in Manistee County in the U.S. state of Michigan. The population was 411 at the 2010 census. The village is located on the shores of Portage Lake and is surrounded by Onekama Township. The town's name is derived from "Ona-ga-maa," an Anishinaabe word which means "singing water." Geography According to the United States Census Bureau, the village has a total area of , all land. The M-22 highway runs through downtown Onekama. History The predecessor of the village of Onekama was the settlement of Portage at Portage Point, first established in 1845, at the western end of Portage Portage or portaging (Canada: ; ) is the practice of carrying water craft or cargo over land, either around an obstacle in a river, or between two bodies of water. A path where items are regularly carried between bodies of water is also called a ..., at the outlet of Portage Creek. In 1871, when landowners around the land-locked lake became exasperated with the practices of th ...
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Hydroxyanthraquinone
A hydroxyanthraquinone (formula: C14H9O2(OH)) is any of several organic compounds that can be viewed as derivatives of an anthraquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). The IUPAC nomenclature recommends hydroxyanthracenedione. Usually "hydroxyanthraquinone" refers to a derivative of 9,10-anthraquinone. Quoted by Khalafy and Bruce. Quoted by Khalafy and Bruce. Isomers In general, the term may mean any anthraquinone 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 8) is indicated by a multiplier prefix A prefix is an affix which is placed before the Word stem, stem of a word. Adding it to the beginning of one word changes it into another word. For example, when the prefix ''un-'' is added to the word ''happy'', it creates the word ''unhappy'' ... (mono-, di-, tri-, up to octa-). Additional hydroxy- compounds can be derived f ...
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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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