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Anthraquinones

January 01, 1970

For the parent molecule 9,10-anthraquinone, see anthraquinone

Structure proposed for the pigment carmine.

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.

The name "anthraquinone" was first used by German chemists Carl Graebe and Carl Theodore Liebermann in a 1868 publication describing the chemical synthesis of the red dye alizarin from anthracene, a component of coal tar. This discovery led to the industrial production of alizarin and the impetus for further research on anthraquinone chemistry.[1]

Occurrence in plants edit

 
The yellow color of certain lichens, particularly in the family Teloschistaceae (here Variospora thallincola), is due to the presence of anthraquinones.[2]

Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and cascara buckthorn, fungi, lichens, and some insects. A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium Photorhabdus luminescens.[3] Chorismate, formed by isochorismate synthase in the shikimate pathway, is a precursor of anthraquinones in Morinda citrifolia.[4] Tests for anthraquinones in natural extracts have been established.[5]

Applications edit

In the production of hydrogen peroxide edit

A large industrial application of anthraquinones is for the production of hydrogen peroxide. 2-Ethyl-9,10-anthraquinone or a related alkyl derivative is used, rather than anthraquinone itself.[7]

 
Catalytic cycle for the anthraquinone process to produce hydrogen peroxide.

Millions of tons of hydrogen peroxide are manufactured by the anthraquinone process.[8]

Pulping edit

Sodium 2-anthraquinonesulfonate (AMS) is a water-soluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes.[9]

Dyestuff precursor edit

Main article: Anthraquinone dyes

The 9,10-anthraquinone skeleton occurs in many dyes, such as alizarin.[10] Important derivatives of 9,10-anthraquinone are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.[11]

 
Selection of anthraquinone dyes. From the left: C.I.Acid Blue 43 an "acid dye" for wool (also called "Acilan Saphirol SE"), C.I. Vat Violet 1, which is applied by transfer printing using sublimation, a blue colorant commonly used in gasoline, and C.I. Disperse Red 60.

Medicine edit

Derivatives of 9,10-anthraquinone include drugs such as the anthracenediones and the anthracycline family of chemotherapy drugs. The latter drugs are derived from the bacterium Streptomyces peucetius, discovered in a soil sample near the Adriatic sea. Drugs in the anthraquinone family include the prototypical daunorubicin, doxorubicin, mitoxantrone, losoxantrone, and pixantrone. Most of these drugs, with the notable exception of pixantrone, are extremely cardiotoxic, causing irreversible cardiomyopathy, which can limit their practical usefulness in cancer treatment.[11]

The anthracenediones also include

Dantron, emodin, and aloe emodin, and some of the senna glycosides have laxative effects. Prolonged use and abuse leads to melanosis coli.[13][14]

References edit

  1. ^ Phillips, Max (1929). "The chemistry of anthraquinone". Chemical Reviews. 6 (1): 157–174. doi:10.1021/cr60021a007.
  2. ^ Llewellyn, Theo; Nowell, Reuben W.; Aptroot, Andre; Temina, Marina; Prescott, Thomas A.K.; Barraclough, Timothy G.; Gaya, Ester (2023). "Metagenomics shines light on the evolution of "sunscreen" pigment metabolism in the Teloschistales (lichen-forming Ascomycota)". Genome Biology and Evolution. 15 (2): evad002. doi:10.1093/gbe/evad002. PMC 9907504. PMID 36634008.
  3. ^ Brachmann, AO; Joyce, SA; Jenke-Kodama, H; Schwär, G; Clarke, DJ; Bode, HB (2007). "A type II polyketide synthase is responsible for anthraquinone biosynthesis in Photorhabdus luminescens". ChemBioChem. 8 (14): 1721–8. doi:10.1002/cbic.200700300. PMID 17722122.
  4. ^ Stalman, M; Koskamp, AM; Luderer, R; Vernooy, JH; Wind, JC; Wullems, GJ; Croes, AF (2003). "Regulation of anthraquinone biosynthesis in cell cultures of Morinda citrifolia". Journal of Plant Physiology. 160 (6): 607–14. doi:10.1078/0176-1617-00773. PMID 12872482.
  5. ^ Akinjogunla OJ, Yah CS, Eghafona NO, Ogbemudia FO (2010). "Antibacterial activity of leave extracts of Nymphaea lotus (Nymphaeaceae) on Methicillin resistant Staphylococcus aureus (MRSA) and Vancomycin resistant Staphylococcus aureus (VRSA) isolated from clinical samples". Annals of Biological Research. 1 (2): 174–184.
  6. ^ Dapson, R. W.; Frank, M.; Penney, D. P.; Kiernan, J. A. (2007). "Revised procedures for the certification of carmine (C.I. 75470, Natural red 4) as a biological stain". Biotechnic & Histochemistry. 82 (1): 13–15. doi:10.1080/10520290701207364. PMID 17510809.
  7. ^ Goor, G.; Glenneberg, J.; Jacobi, S. (2007). "Hydrogen Peroxide". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_443.pub2. ISBN 978-3527306732.
  8. ^ Campos-Martin, Jose M.; Blanco-Brieva, Gema; Fierro, Jose L. G. (2006). "Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process". Angewandte Chemie International Edition. 45 (42): 6962–6984. doi:10.1002/anie.200503779. PMID 17039551.
  9. ^ "Anthraquinone / Alkali Pulping - A Literature Review" (PDF). Project 3370. Appleton, Wisconsin: The Institute of Paper Chemistry. 1978-07-05.
  10. ^ Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN 978-3527306732.
  11. ^ a b Vogel, A. "Anthraquinone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_347. ISBN 978-3527306732.
  12. ^ Panigrahi, G.K.; Suthar, M.K.; Verma, N.; Asthana, S.; Tripathi, A.; Gupta, S.K.; Saxena, J. K.; Raisuddin, S.; Das, M. (2015). "Investigation of the interaction of anthraquinones of Cassia occidentalis seeds with bovine serum albumin by molecular docking and spectroscopic analysis: Correlation to their in vitro cytotoxic potential". Food Research International. 77: 368–377. doi:10.1016/j.foodres.2015.08.022.
  13. ^ Müller-Lissner, S. A. (1993). "Adverse Effects of Laxatives: Fact and Fiction". Pharmacology. 47 (Suppl 1): 138–145. doi:10.1159/000139853. PMID 8234421.
  14. ^ Moriarty, K. J.; Silk, D. B. (1988). "Laxative Abuse". Digestive Diseases. 6 (1): 15–29. doi:10.1159/000171181. PMID 3280173.

January 01, 1970
anthraquinones, parent, molecule, anthraquinone, anthraquinone, structure, proposed, pigment, carmine, also, known, anthraquinonoids, class, naturally, occurring, phenolic, compounds, based, anthraquinone, skeleton, they, widely, used, industrially, occur, nat. For the parent molecule 9 10 anthraquinone see anthraquinone Structure proposed for the pigment carmine 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 The name anthraquinone was first used by German chemists Carl Graebe and Carl Theodore Liebermann in a 1868 publication describing the chemical synthesis of the red dye alizarin from anthracene a component of coal tar This discovery led to the industrial production of alizarin and the impetus for further research on anthraquinone chemistry 1 Contents 1 Occurrence in plants 2 Applications 2 1 In the production of hydrogen peroxide 2 2 Pulping 2 3 Dyestuff precursor 2 4 Medicine 3 ReferencesOccurrence in plants edit nbsp The yellow color of certain lichens particularly in the family Teloschistaceae here Variospora thallincola is due to the presence of anthraquinones 2 Natural pigments that are derivatives of anthraquinone are found inter alia in aloe latex senna rhubarb and cascara buckthorn fungi lichens and some insects A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium Photorhabdus luminescens 3 Chorismate formed by isochorismate synthase in the shikimate pathway is a precursor of anthraquinones in Morinda citrifolia 4 Tests for anthraquinones in natural extracts have been established 5 Senna glycosides from the senna Frangulin in Frangula alnus Aloe emodin in aloe resin Carmine a bright red pigment derived from insects 6 Hypericin and fagopyrin are naphthodianthrones anthraquinone derivatives Applications editIn the production of hydrogen peroxide edit A large industrial application of anthraquinones is for the production of hydrogen peroxide 2 Ethyl 9 10 anthraquinone or a related alkyl derivative is used rather than anthraquinone itself 7 nbsp Catalytic cycle for the anthraquinone process to produce hydrogen peroxide Millions of tons of hydrogen peroxide are manufactured by the anthraquinone process 8 Pulping edit Sodium 2 anthraquinonesulfonate AMS is a water soluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes 9 Dyestuff precursor edit Main article Anthraquinone dyes The 9 10 anthraquinone skeleton occurs in many dyes such as alizarin 10 Important derivatives of 9 10 anthraquinone are 1 nitroanthraquinone anthraquinone 1 sulfonic acid and the dinitroanthraquinone 11 nbsp Selection of anthraquinone dyes From the left C I Acid Blue 43 an acid dye for wool also called Acilan Saphirol SE C I Vat Violet 1 which is applied by transfer printing using sublimation a blue colorant commonly used in gasoline and C I Disperse Red 60 Medicine edit Derivatives of 9 10 anthraquinone include drugs such as the anthracenediones and the anthracycline family of chemotherapy drugs The latter drugs are derived from the bacterium Streptomyces peucetius discovered in a soil sample near the Adriatic sea Drugs in the anthraquinone family include the prototypical daunorubicin doxorubicin mitoxantrone losoxantrone and pixantrone Most of these drugs with the notable exception of pixantrone are extremely cardiotoxic causing irreversible cardiomyopathy which can limit their practical usefulness in cancer treatment 11 The anthracenediones also include Antimalarials such as rufigallol DNA dyes nuclear counterstains such as DRAQ5 DRAQ7 and CyTRAK Orange for flow cytometry and fluorescence microscopy Anthraquinone derivatives rhein emodin aloe emodin parietin physcion and chrysophanol extracted from Cassia occidentalis are toxic and known to cause hepatomyoencephalopathy in children 12 nbsp Aloe emodin nbsp Daunorubicin nbsp Mitoxantrone nbsp Pixantrone Dantron emodin and aloe emodin and some of the senna glycosides have laxative effects Prolonged use and abuse leads to melanosis coli 13 14 References edit Phillips Max 1929 The chemistry of anthraquinone Chemical Reviews 6 1 157 174 doi 10 1021 cr60021a007 Llewellyn Theo Nowell Reuben W Aptroot Andre Temina Marina Prescott Thomas A K Barraclough Timothy G Gaya Ester 2023 Metagenomics shines light on the evolution of sunscreen pigment metabolism in the Teloschistales lichen forming Ascomycota Genome Biology and Evolution 15 2 evad002 doi 10 1093 gbe evad002 PMC 9907504 PMID 36634008 Brachmann AO Joyce SA Jenke Kodama H Schwar G Clarke DJ Bode HB 2007 A type II polyketide synthase is responsible for anthraquinone biosynthesis in Photorhabdus luminescens ChemBioChem 8 14 1721 8 doi 10 1002 cbic 200700300 PMID 17722122 Stalman M Koskamp AM Luderer R Vernooy JH Wind JC Wullems GJ Croes AF 2003 Regulation of anthraquinone biosynthesis in cell cultures of Morinda citrifolia Journal of Plant Physiology 160 6 607 14 doi 10 1078 0176 1617 00773 PMID 12872482 Akinjogunla OJ Yah CS Eghafona NO Ogbemudia FO 2010 Antibacterial activity of leave extracts of Nymphaea lotus Nymphaeaceae on Methicillin resistant Staphylococcus aureus MRSA and Vancomycin resistant Staphylococcus aureus VRSA isolated from clinical samples Annals of Biological Research 1 2 174 184 Dapson R W Frank M Penney D P Kiernan J A 2007 Revised procedures for the certification of carmine C I 75470 Natural red 4 as a biological stain Biotechnic amp Histochemistry 82 1 13 15 doi 10 1080 10520290701207364 PMID 17510809 Goor G Glenneberg J Jacobi S 2007 Hydrogen Peroxide Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a13 443 pub2 ISBN 978 3527306732 Campos Martin Jose M Blanco Brieva Gema Fierro Jose L G 2006 Hydrogen Peroxide Synthesis An Outlook beyond the Anthraquinone Process Angewandte Chemie International Edition 45 42 6962 6984 doi 10 1002 anie 200503779 PMID 17039551 Anthraquinone Alkali Pulping A Literature Review PDF Project 3370 Appleton Wisconsin The Institute of Paper Chemistry 1978 07 05 Bien H S Stawitz J Wunderlich K 2005 Anthraquinone Dyes and Intermediates Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 355 ISBN 978 3527306732 a b Vogel A Anthraquinone Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 347 ISBN 978 3527306732 Panigrahi G K Suthar M K Verma N Asthana S Tripathi A Gupta S K Saxena J K Raisuddin S Das M 2015 Investigation of the interaction of anthraquinones of Cassia occidentalis seeds with bovine serum albumin by molecular docking and spectroscopic analysis Correlation to their in vitro cytotoxic potential Food Research International 77 368 377 doi 10 1016 j foodres 2015 08 022 Muller Lissner S A 1993 Adverse Effects of Laxatives Fact and Fiction Pharmacology 47 Suppl 1 138 145 doi 10 1159 000139853 PMID 8234421 Moriarty K J Silk D B 1988 Laxative Abuse Digestive Diseases 6 1 15 29 doi 10 1159 000171181 PMID 3280173 Retrieved from https en wikipedia org w index php title Anthraquinones amp oldid 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