Natural Anthraquinone
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Natural Anthraquinone
''For the parent molecule 9,10-anthraquinone, see anthraquinone'' Anthraquinones (also known as anthraquinonoids) are a class of naturally occurring phenolic compounds based on the 9,10-anthraquinone skeleton. They are widely used industrially and occur naturally. Occurrence in plants : Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna (plant), senna, rhubarb, and rhamnus purshiana, cascara buckthorn, fungi, lichens, and some insects. A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium ''Photorhabdus luminescens''. Chorismate, formed by isochorismate synthase in the shikimate pathway, is a precursor of anthraquinones in ''Morinda citrifolia''. Tests for anthraquinones in natural extracts have been established. *Senna glycosides from the Senna (plant), senna. *Frangulin in Frangula alnus. *Aloe-emodin in aloe resin. *Carmine, a bright-red pigment derived from insects. *Hypericin and fagopyrin ...
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Anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the 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. 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. Synthesis There are several current industrial methods to produce 9,10-anthraquinone: # The oxidation of anthracene. Chromium(VI) is the typical oxidant. # The Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for produc ...
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Senna (plant)
''Senna'', the sennas, is a large genus of flowering plants in the legume family (Fabaceae, subfamily Caesalpinioideae, tribe Cassieae). This diverse genus is native throughout the tropics, with a small number of species in temperate regions. The number of species is estimated to be from about 260 to 350.Randell, B. R. and B. A. Barlow. 1998. ''Senna''. pp 89-138. In: A. S. George (executive editor). ''Flora of Australia'' volume 12. Australian Government Publishing Service: Canberra, Australia. The type species for the genus is ''Senna alexandrina''. About 50 species of ''Senna'' are known in cultivation.Huxley, A., et al. (1992). ''The New Royal Horticultural Society Dictionary of Gardening''. The Macmillan Press, Limited: London. The Stockton Press: New York. (set). Description ''Senna'' includes herbs, shrubs, and tree In botany, a tree is a perennial plant with an elongated stem, or trunk, usually supporting branches and leaves. In some usages, the definition o ...
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Anthracycline
Anthracyclines are a class of drugs used in cancer chemotherapy that are extracted from ''Streptomyces'' bacterium. These compounds are used to treat many cancers, including leukemias, lymphomas, breast, stomach, uterine, ovarian, bladder cancer, and lung cancers. The first anthracycline discovered was daunorubicin (trade name Daunomycin), which is produced naturally by ''Streptomyces peucetius'', a species of Actinomycetota. Clinically the most important anthracyclines are doxorubicin, daunorubicin, epirubicin and idarubicin. The anthracyclines are among the most effective anticancer treatments ever developed and are effective against more types of cancer than any other class of chemotherapeutic agents. Their main adverse effect is cardiotoxicity, which considerably limits their usefulness. Use of anthracyclines has also been shown to be significantly associated with cycle 1 severe or febrile neutropenia. Other adverse effects include vomiting. The drugs act mainly by interc ...
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Alizarin
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 ligh ...
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Sodium 2-anthraquinonesulfonate
Sodium 2-anthraquinonesulfonate (AMS) is a water-soluble anthraquinone derivative. In the laboratory it could be prepared by sulfonation of anthraquinone. Digester additive in papermaking AMS is used as a catalyst in production of alkaline pulping in the soda process. It goes through a redox cycle similar to that of anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxo ... to give a catalytic effect. AMS was discovered as an efficient pulping catalyst before anthraquinone, but has a higher cost. References {{reflist Anthraquinones Sulfonates Organic sodium salts ...
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Anthraquinone Process
The anthraquinone process is a process for the production of hydrogen peroxide, which was developed by BASF. The industrial production of hydrogen peroxide is based on the reduction of oxygen, as in the direct synthesis from the elements. Instead of hydrogen itself, however, a 2-alkyl-anthrahydroquinone, which is generated before from the corresponding 2-alkyl-anthraquinone by catalytic hydrogenation with palladium is used. Oxygen and the organic phase react under formation of the anthraquinone and hydrogen peroxide. Among other alkyl groups (R) ethyl- and ''tert''-butyl- are used, e.g., 2-ethylanthraquinone. The hydrogen peroxide is then extracted with water and in a second step separated by fractional distillation from the water. The hydrogen peroxide accumulates as sump product. The anthraquinone acts as a catalyst, the overall reaction equation is therefore: : + → If ozone Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale ...
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2-Ethyl-9,10-anthraquinone
2-Ethylanthraquinone is an organic compound that is a derivative of anthraquinone. This pale yellow solid is used in the industrial production of hydrogen peroxide (H2O2).Römpp CD 2006, Georg Thieme Verlag 2006 Production 2-Ethylanthraquinone is prepared from the reaction of phthalic anhydride and ethylbenzene: :C6H4(CO)2O + C6H5Et → C6H4(CO)2C6H3Et + H2O. Both phthalic anhydride and ethylbenzene are readily available, being otherwise used in the large-scale production of plastics. Uses Hydrogen peroxide is produced industrially by the anthraquinone process which involves using 2-alkyl-9,10-anthraquinones for hydrogenation. Many derivatives of anthraquinone are used but 2-ethylanthraquinone is common because of its high selectivity. The hydrogenation of the unsubstituted ring can reach 90% selectivity by using 2-ethylanthraquinone. Hydrogenation follows the Riedl-Pfleiderer, or autoxidation, process: The hydrogenation of 2-ethylanthraquinone 2-Ethylanthraq ...
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Hydrogen Peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%–6% by weight) in water for consumer use, and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or " high-test peroxide", decomposes explosively when heated and has been used as a propellant in rocketry. Hydrogen peroxide is a reactive oxygen species and the simplest peroxide, a compound having an oxygen–oxygen single bond. It decomposes slowly when exposed to light, and rapidly in the presence of organic or reactive compounds. It is typically stored with a stabilizer in a weakly acidic solution in a dark bottle to block light. Hydrogen peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases. Properties The boiling poi ...
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Fagopyrin
Fagopyrin is a term used for several closely related naturally occurring substances in the buckwheat plant. Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. Fagopyrin is located almost exclusively in the cotyledons of the buckwheat herb. When ingested, fagopyrins cause sensitivity to light. References External linksPhytopharmaka VII: Forschung und klinische Anwendung Piperidines Phenols Plant toxins Quinones {{aromatic-stub ...
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Hypericin
Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of ''Hypericum'' (Saint John's wort). Hypericin is believed to act as an antibiotic, antiviral and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine. It was initially believed that the anti-depressant pharmacological activity of hypericin was due to inhibition of monoamine oxidase enzyme. The crude extract of ''Hypericum'' is a weak inhibitor of MAO-A and MAO-B. Isolated hypericin does not display this activity, but does have some affinity for NMDA receptors. This points in the direction that other constituents are responsible for the MAOI effect. The current belief is that the mechanism of antidepressant activity is due to the inhibition of re-uptake of certain neurotransmitters. The large ...
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