Anthraquinone derivatives pdf

Continue 9,10-Anthraquinone Names IUPAC name Anthraquinone Other names 9,10-AnthracenedioneAnthradione9,10-AnthrachinonAnthracene-9,10-quinone9,10-Dihydro-9,10-dioxoanthraceneHoeliteMorkitCorbit Identifiers CAS Number 84-65-1 Y 3D model (JSmol) Interactive image Beilstein Reference 390030 ChEBI CHEBI:40448 N ChEMBL ChEMBL55659 N ChemSpider 6522 Y ECHA InfoCard 100.001.408 Gmelin Reference 102870 KEGG C16207 Y PubChem CID 6780 RTECS number CB4725000 UNII 030MS0JBDO UN number 3143 CompTox Dashboard (EPA) DTXSID3020095 InChI InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8HKey: RZVHIXYEVGDQDX-UHFFFAOYSA-N SMILES O=C1c2ccccc2C(=O)c3ccccc13 Properties Chemical formula C14H8O2 Molar mass 208.216 g·mol−1 Appearance yellow solid Density 1.308 g/cm3 Melting point 286 °C (547 °F; 559 K) Boiling point 379.8 °C (715.6 °F; 653.0 K) Solubility in water insoluble Hazards GHS pictograms GHS Signal word Danger GHS hazard statements H350 GHS precautionary statements P201 , P202, P281, P308+313, P405, P501 Flash point 185 °C (365 °F; 458 K) Related compounds Related compounds quinone, anthracene, unless otherwise specified, standard-state material data (at 25 °C [77 °F], 100 kPa). N check (what is YN?) Infobox links Anthraquinone, also called anthracenedion or dioxoantracene, is an aromatic organic compound with the formula C14H8O2. Isomers include various quinone derivatives. The term anthraquinone, however, refers to the isomer, 9,10-antraquinone (IUPAC: 9,10-dioxanthracene), in which the caste groups are located on the central ring. It is a building block of many paints and is used for the production of bleach pulp paper. It is a yellow, highly crystalline solid, poorly soluble in water, but soluble in a hot organic solvent. 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 a rare mineral hoelite. Synthesis There are several current industrial methods of producing 9,10-antraquinone: anthracene oxidation, a reaction that is localized in the central ring. Chromium (VI) is a typical oxidiser. Reaction of the benzene and phthal anhydride friedel-crafts with the participation of AlCl3, producing o-benzoylbenzencarboxylic acid, which is then added, by forming anthraquinone. This reaction is useful in the production of modified anthraquinones. Reaction of naphthine and butadiene dieler, followed by oxidative dehydrogenation Acid-catalysed styrene dimerization to obtain 1,3-diphenylbutene, which can then be transformed into blackiquinone. [1] This process was initiated by BASF. It also arises through rickert-alder reaction, retro-Diels-Alder reaction. Reactions Hydroanthraquinone (secondhydroquinone). Reduction with copper gives anron. [2] Sulphonation with sulphuric acid anthroquinone-1-sulfonic acid[3], which reacts with sodium chlorate and gives 1-chloroanthequinone. [4] Application See also: Anthraquinone Digester additive paper production 9,10-antraquinone is used as a digester additive in the manufacture of paper pulp alkaline processes such as Kraft, alkaline sulphite or Soda-AQ processes. Anthraquinone is a catalyst for redox. The mechanism of action may include a single electron transmission (SET). [5] Anthraquinone oxidizes the polysaccharide reduction end in cellulose, i.e. cellulose and hemicellulose, thereby preventing alkaline degradation (peeling). Anthraquinone is reduced to 9,10- dihydroxycyancycene, which can then react with lignin. Lignin is degraded and becomes water, making it easier to wash off the pulp, and anthraquinone is recovered. This process gives an increase in pulp output, usually 1-3% and a decrease in the number of cappa. [6] Niche 9,10-anthraquinone is used as a bird repellent for seeds and as a gas generator in satellite cylinders. It was also mixed with lanolon and used as a wool spray to protect flocks of sheep from kea attacks in New Zealand. [8] Other isomers Several other anthraquinone isomers, including 1,2,4-, and 2,6-anthraquinones are available. They are relatively insignificant. The term is also used for a more general sense of any compound that can be seen as a form of anthraquinone with some hydrogen atophageals replaced by other atophageal or functional groups. These derivatives include materials that are technically useful or play an important role in living beings. Recently, a class of antraquinone derivatives has been shown to have self-healing properties when doped in the PMMA matrix. [9] Safety Anthraquinone is not registered in LD50, probably because it is so insoluble in water. Many drugs are derivatives of anthroquinone. [1] From a metabolic point of view of modified anthraquinones, the enzyme encoded by the gene UGT1A8 acts on glucuronidase rich in substrates, including anthraquinones. [10] See also Ullmann's encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. Doi:10.1002/14356007.a02_347. 10000000000000000000000000000000 Allen, C.F.H. (1934). Benzanthrone. Organic Fusion. 14: 4. Doi:10.15227/orgsyn.014.0004. Cite contains an empty unknown parameter: |1= (help) ^ Scott, W.J.; Allen, C.F. H. (1938). Potassium anthraquinone α-sulfonate. Organic Fusion. 18: 72. Doi:10.15227/orgsyn.018.0072. 20:00: Mindaugas Jokubauskas; Allen, C.F. H. (1938). α-chloranthraquinone. Organic Fusion. 18: 15. Doi:10.15227/orgsyn.018.0015. 2008 – Samp. Detailed mechanism for the transfer of anthraquinone mass in alkaline pulp (Disesis). Georgia Institute of Technology. 30(30). hdl:1853/24767. 20:000 Sturgeoff, L.G.; Pitl, Y. (1997) [1993]. Small Kappa Pulping capital investments. Goyal, G.C. (ed.). Anthraquinone pulp. TAPPI Press. On pages 3-9, Isbn 0-89852-340-0. ^ www.americanheritage.com. Archived since the original 2009-06-09. Retrieved 22/09/2009. 29, 2012, in Adam Dudding. How to solve a problem like kea. Sunday star times. New Zealand. Retrieved 11 November 2014 ↑ Ramini, Shiva K.; Kuzyk, Mark G. (2012-08-07). A pattern of self-healing based on polymer-induced chromophore correlations. Journal of Chemical Physics. 137 (5): 054705. 1205.0481. Bibcode:2012JChPh.137e4705R. doi:10.1063/1.4739295. issn 0021-9606. PMID 22894369. 1980 Chen, F.; Shan, Y. Y. Tran, H.M.; Kimura, S.; Yeatman, M.T.; Owens, I. S. (1992). The new complex Locus UGT1 encodes human bilirubin, phenol and other UDP-glucuronosyltransferase Isozymes with identical carboxyl Termini (PDF). Journal of Biological Chemistry. 267 (5): 3257–3261. PMID 1339448. External connections national contaminant inventory - polycyclic aromatic hydrocarbons fact sheet molecules spontaneously form a honeycomb network derived from For the primary molecule 9,10-anthraquinone, see the anthraquinone structure of the proposed pigment carmine. Anthraquinones (also known as antrachinonoids) is a class of natural phenolic compounds based on 9,10-anthraquinone skeleton skeleton. They are widely used in an industrial way and occur naturally. The appearance of plants In the yellow color of certain lichens (here Caloplaca tallincola) is due to the presence of anthraquinones. Natural pigments, which are derivatives of anthraquinone, are found, inter alia, in aloe latex, senna, rhubarb and cascara in sea buckthorn, mushrooms, lichen and some insects. Type II polyketid sintasis is responsible for the biosynthesis of anthraquinone bacterium Photorhabdus luminescens. [1] Chorismat, which consists of isochorismato sintaase in the pathway of shikimate, is the precursor of anthraquinones Morinda citrifolia. [2] Anthraquinone tests have been established in natural extracts. Senna glycosides from senna. Frangulin Frangula alnus. Aloe- emodin in aloe vera resin. Carmine , a bright red pigment obtained from insects. [4] Hypericin and phagopyran are nafthodianthrones, derivatives of anthraquinone. Use in the production of hydrogen peroxide High industrial use of anthraquinones is intended for the production of hydrogen peroxide. 2-ethyl-9,10-anthraquinone or associated alkyl derivative, rather than anthraquinone itself, is used. [5] Catalytic cycle for the anthraquinone process for the production of hydrogen peroxide. Millions of tons of hydrogen peroxide are produced during the anthraquinone process. [6] Cellulose sodium 2-anthraquinoufonate (AMS) is a water-soluble derivative of anthraquinone which was the first derivative of antraquinone which was found to have a catalytic effect pulp processes. [7] Colouring defect Basic product: Anthraquinone dyes 9,10-antraquinone skeleton appear in many colours such as alizarin. [8] Important derivatives of 9,10-anthraquinone are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid and dinitroanthraquinone. [9] Selection of anthraquinone paints. From left: C.I.Acid Blue 43 is an acid dye wool (also called Acilan Saphirol SE), C.I. Vat Violet 1, which is applied to transmission printing using sublimation, blue dye commonly used in gasoline, and C.I. Disperse Red 60. Medical derivatives of 9.10-antraquinone are many important drugs (collectively called anthracenedions). They include laxatives, such as dantron, emodine, and aloe emodin, and some senna glycosides antimalarials such as rufigallol Antineoplastics used in the treatment of cancer, such as mitoxantrone, pixantrone, and anthracycline DNA colorants/nuclear counters such as DRAQ5, DRAQ7 and CyTRAK Orange flow cytometry fluorescence and microscopy. Derivatives of antinone: rhine, emodin, aloe emodine, parietine (fiscionas) and chrysophool extracted from Cassia occidentalis are toxic and are known to cause hepatomyoencephalopathy in children. Aloe emodin Mitoxantrone Pixantrone Pixantrone Natural derivatives of antraquinone usually have a laxative effect. Long-term use and abuse causes melanosis coli. [11] [12] 5 anthraquinones have been shown to inhibit tau aggregate formation and dissolve paired screw threads considered essential for the progression of Alzheimer's disease in both mouse models and in vitro tests, but have not been studied as a therapeutic substance. [13] References ^ Brachmann, AO; Joyce, SA; Jenke-Kodama, H; Schwär, G; Clarke, DJ; Bode, HB (2007). Type II poctindide sintasis is responsible for the biosynthesis of anthraquinone Photorhabdus luminescens. ChemBioChem: European Journal of Chemical Biology. 8 (14): 1721–8. 200700300. PMID 17722122. 2014 Koskamp, AM; Luderer, R; Vernooy, JH; Wind, JC; Wullems, GJ; Croes, AF (2003). Himinvinan biosinthesis in Morinda citrifolia cell cultures. Journal of Plant Physiology. 160 (6): 607–14. doi:10.1078/0176-1617-00773. PMID 12872482. 2010 – Akinjogunla OJ, Yah CS, Eghafona NO, Ogbemudia FO. Antibacterial activity holiday extracts Nymphaea lotus (Nymphaeaceae) methicillin-resistant Staphylococcus aureus (MRSA) and Vancomicin-resistant Staphylococcus aureus (VRSA) isolated from clinical samples. Annals of biological research. 1 (2): 174–184. 1980 – Dawson; Frank, M.; Penney, D.P.; Kiernan, J.A. (2007). Revised carmine certification procedures (C.I. 75470, Natural rev 4) as biological spots. Biotechnology and histochemistry. 82 (1): 13–15. doi:10.1080/10520290701207364. PMID 17510809. 1980 g. Glenneberg, J.; Jacobi, S. (2007). Hydrogen peroxide. Encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. Doi:10.1002/14356007.a13_443.pub2. Isbn 978-3527306732. 1980 – Campos-Martin; Blanco-Brieva, Gema; 2006 Hydrogen Peroxide Synthesis: The outlook for the anthraquine process. Angewandte Chemie International Edition. 45 (42): 6962–6984. doi:10.1002/anie.200503779. PMID 17039551. ↑ Anthraquinone / Alkali pulp - literature review (PDF). Project 3370. Appleton, Wisconsin: Paper Chemistry Institute. 1978-07-05. ^ Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). Anthraquinone dyes and intermediate products Ullmann's encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. 1980 – Vogel. Ullmann's encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. Doi:10.1002/14356007.a02_347. 1988 – Panigrahi; Suthar, M.K.; Verma, N.; Asthana, S.; Tripathi, A.; Gupta, S.K.; Saksena, J.K.; Raisuddin, S.; Das, M. (2015). Cassia occidentalis test for the interaction of anthraquinones of seeds with bovine serum albumin by molecular connection and spectroscopic analysis: correlation with their cytotoxic potential in vitro. Food Research International. 77: 368–377. Doi:10.1016/j.foodres.2015.08.022. 1993 – Müller-Lissner( 1993). Undesirable effects of laxatives: fact and fiction. Pharmacology. 47 (Annex 1): 138-145. Doi:10.1159/000139853. PMID 8234421. 1 January 1980 Silk, D. B. (1988). Laxative abuse. Digestive diseases. 6 (1): 15–29. Doi:10.1159/000171181. PMID 3280173. 1999 Gazova, Z.; von Bergen, M.; Khlistunova, I.; Wang, Y.; Hascher, A.; Mandelkow, E.M.; Biernat, J.; Mandelkow, E. (2005). Anthraquinones inhibit Tau aggregation and dissolve Alzheimer's paired spiral filaments in vitro and cells (PDF). Journal of Biological Chemistry. 280 (5): 3628–3635. Doi:10.1074/jbc. M410984200. PMID 15525637. Retrieved from 2 9,10-Anthraquinone Names IUPAC name Anthraquinone Other names 9,10-AnthracenedioneAnthradione9,10-AnthrachinonAnthracene-9,10-quinone9,10-Dihydro-9,10-dioxoanthraceneHoeliteMorkitCorbit Identifiers CAS Number 84-65-1 Y 3D model (JSmol) Interactive image Beilstein Reference 390030 ChEBI CHEBI:40448 N ChEMBL ChEMBL55659 N ChemSpider 6522 Y ECHA InfoCard 100.001.408 Gmelin Reference 102870 KEGG C16207 Y PubChem CID 6780 RTECS number CB4725000 UNII 030MS0JBDO UN number 3143 CompTox Dashboard (EPA) DTXSID3020095 InChI InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8HKey: RZVHIXYEVGDQDX-UHFFFAOYSA-N SMILES O=C1c2ccccc2C(=O)c3ccccc13 Properties Chemical formula C14H8O2 Molar mass 208.216 g·mol−1 Appearance yellow solid Density 1.308 g/cm3 Melting point 286 °C (547 °F; 559 K) Boiling point 379.8 °C (715.6 °F; 653.0 K) Solubility in water insoluble GHS pictogram GHS signal word Danger GHS hazard statements H350 GHS precautionary statements P201, P202, P281, P308+313, P405, P501 Flash point 185 °C (365 °F; 458 K) Related compounds quinone, anthracene, unless otherwise specified, standard-state material data (at 25 °C [77 °F], 100 kPa). N check (what is YN?) Infobox links Anthraquinone, also called anthracenedion or dioxoantracene, is an aromatic organic compound with the formula C14H8O2. Isomers include various quinone derivatives. The term anthraquinone, however, refers to the isomer, 9,10-antraquinone (IUPAC: 9,10-dioxanthracene), in which the caste groups are located on the central ring. It is a building block of many paints and is used for the production of bleach pulp paper. It is a yellow, highly crystalline solid, poorly soluble in water, but soluble in a hot organic solvent. 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 a rare mineral hoelite. Synthesis There are several current industrial methods of producing 9,10-antraquinone: anthracene oxidation, a reaction that is localized in the central ring. Chromium (VI) is a typical oxidiser. Reaction of the benzene and phthal anhydride friedel-crafts with the participation of AlCl3, producing o-benzoylbenzencarboxylic acid, which is then added, by forming anthraquinone. This reaction is useful in the production of modified anthraquinones. Reaction of naphthine and butadiene dieler, followed by oxidative dehydrogenation Acid-catalysed styrene dimerization to obtain 1,3-diphenylbutene, which can then be transformed into blackiquinone. [1] This process was initiated by BASF. It also arises through rickert-alder reaction, retro-Diels-Alder reaction. Reactions Hydroanthraquinone (secondhydroquinone). Reduction with copper gives anron. [2] Sulphonation with sulphuric acid provides anthroquinone-1-sulfonic acid[3], which reacts with sodium chlorate to give 1-chloranothequinone. [4] Application See also: Anthraquinone Digester additive paper production 9,10-antraquinone is used as a digester additive in the manufacture of paper pulp alkaline processes such as Kraft, alkaline sulphite or Soda-AQ processes. Anthraquinone is a catalyst for redox. The mechanism of action may include a single electron transmission (SET). [5] Anthraquinone oxidizes the polysaccharide reduction end in cellulose, i.e. cellulose and hemicellulose, thereby preventing alkaline degradation (peeling). Anthraquinone is reduced to 9,10-dihydroxycyancycene, which can then react with lignin. Lignin is degraded and becomes water, making it easier to wash off the pulp, and anthraquinone is recovered. This process allows for an increase in usually 1-3% and a decrease in the number of cappa. [6] Niche 9,10-anthraquinone is used as a bird repellent for seeds and as a gas generator in satellite cylinders. It was also mixed with lanolon and used as a wool spray to protect flocks of sheep from kea attacks in New Zealand. [8] Other isomers Several other anthraquinone isomers, including 1,2,4-, and 2,6-anthraquinones are available. They are relatively insignificant. The term is also used for a more general sense of any compound that can be seen as a form of anthraquinone with some hydrogen atophageals replaced by other atophageal or functional groups. These derivatives include materials that are technically useful or play an important role in living beings. Recently, a class of antraquinone derivatives has been shown to have self-healing properties when doped in the PMMA matrix. [9] Safety Anthraquinone is not registered in LD50, probably because it is so insoluble in water. Many drugs are derivatives of anthroquinone. [1] From a metabolic point of view of modified anthraquinones, the enzyme encoded by the gene UGT1A8 acts on glucuronidase rich in substrates, including anthraquinones. [10] See also Ullmann's encyclopedia of industrial chemistry. Weinheim: Wiley-VCH. Doi:10.1002/14356007.a02_347. 10000000000000000000000000000000 Allen, C.F.H. (1934). Benzanthrone. Organic Fusion. 14: 4. Doi:10.15227/orgsyn.014.0004. Cite contains an empty unknown parameter: |1= (help) ^ Scott, W.J.; Allen, C.F. H. (1938). Potassium anthraquinone α-sulfonate. Organic Fusion. 18: 72. Doi:10.15227/orgsyn.018.0072. 20:00: Mindaugas Jokubauskas; Allen, C.F. H. (1938). α-chloranthraquinone. Organic Fusion. 18: 15. Doi:10.15227/orgsyn.018.0015. 2008 – Samp. Detailed mechanism for the transfer of anthraquinone mass in alkaline pulp (Disesis). Georgia Institute of Technology. 30(30). hdl:1853/24767. 20:000 Sturgeoff, L.G.; Pitl, Y. (1997) [1993]. Small Kappa Pulping without capital investment. Goyal, G.C. (ed.). Anthraquinone pulp. TAPPI Press. On pages 3-9, Isbn 0-89852-340-0. ^ www.americanheritage.com. Archived since the original 2009-06-09. Retrieved 22/09/2009. 29, 2012, in Adam Dudding. How to solve a problem like kea. Sunday star times. New Zealand. Retrieved 11 November 2014 ↑ Ramini, Shiva K.; Kuzyk, Mark G. (2012-08-07). A pattern of self-healing based on polymer-induced chromophore correlations. Journal of Chemical Physics. 137 (5): 054705. 1205.0481. Bibcode:2012JChPh.137e4705R. doi:10.1063/1.4739295. issn 0021-9606. PMID 22894369. 1980 Chen, F.; Shan, Y. Y. Tran, H.M.; Kimura, S.; Yeatman, M.T.; Owens, I. S. (1992). The new complex Locus UGT1 encodes human bilirubin, phenol and other UDP-glucuronosyltransferase Isozymes with identical carboxyl Termini (PDF). Journal of Biological 267 (5): 3257–3261. PMID 1339448. External connections National pollutant inventory - polycyclic aromatic hydrocarbon fact sheet Molecules in spontaneous form Honeycomb network Retrieved from

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