Purpurin is also called verantin, smoke Brown G, hydroxylizaric acid, and C.I. 58205. It is a minor component of the classical lake pigment "madder lake" or Rose Madder.
Madder root has been used for dying cloth at least since 1500 BC.[2] Purpurin and alizarin were isolated from the root by Pierre Robiquet and Colin, two French chemists, in 1826. They were identified as anthracene derivatives by Gräbe and Liebermann in 1868. They also synthesized alizarin from bromoanthraquinone, which, together with the conversion of alizarin into purpurin published previously by M. F. De Lalande, provided the first synthetic route to purpurin.[3] The positions of the OH groups were determined by Bayer and Caro in 1874–1875.[4]
Natural occurrenceedit
Purpurin occurs in the roots of the madder plant (Rubia tinctorum), together with alizarin (1,2-dihydroxyanthraquinone). The root actually contains colorless glycosides of the dyes.
Propertiesedit
Purpurin is a crystalline solid, that forms orange-red needles melting at 259 °C (498 °F).[1] It becomes red when dissolved in ethanol, and yellow when dissolved with alkalis in boiling water. It is insoluble in hexane but soluble in chloroform, and can be obtained from chloroform as reddish needles.[5] Unlike alizarin, purpurin is dissolved by boiling in a solution of aluminium sulfate, from which it can be precipitated by acid. This procedure can be used to separate the two dyes.[6]
Like many dihydroxy- and trihydroxyanthraquinones, pupurin has a purgative action, although only 1/20 as effective as 1,2,7-trihydroxyanthraquinone (anthrapurpurin).[7]
Usesedit
Purpurin is a fast dye for cotton printing and forms complexes with various metal ions. It fades faster than alizarin on exposure to sunlight.[2]
A study published in Nature journal Scientific Reports suggests that the purpurin could replace cobalt in lithium-ion batteries.[8] Eliminating cobalt would mean eliminating a hazardous material, allow batteries to be produced at room temperature, and lower the cost of recycling batteries. Extracting purpurin from farmed madder is a simple task; alternately, the chemical could be synthesized in a lab.[9]
^ abMadder Root 2011-07-14 at the Wayback Machine catalog entry at Natural Pigments website. Accessed on 2010-01-22.
^Chemical news and journal of industrial science, Volume 30, Page 207
^ Wahl, Andre; Atack, F. W (1919) The Manufacture Of Organic Dyestuffs. G. Bell And Sons, Limited. Online version accessed on 2010-01-22.
^Vankar, Padma S.; Shanker, Rakhi; Mahanta, Debajit; Tiwari, S.C. (2008). "Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn. using biomordant". Dyes and Pigments. 76 (1): 207–212. doi:10.1016/j.dyepig.2006.08.023.
^Irving Wetherbee Fay (1919) The chemistry of the coal-tar dyes. Van Nostrand Online version accessed on 2010-01-22.
^Alister McGuigan, Hugh (1921) An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry. P. Blakiston's son, Philadelphia.
^Reddy, Arava Leela Mohana; Nagarajan, Subbiah; Chumyim, Porramate; Gowda, Sanketh R; Pradhan, Padmanava; Jadhav, Swapnil R; Dubey, Madan; John, George; Ajayan, Pulickel M; Ajayan, Pulickel M (2012). "Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes". Scientific Reports. 2: 960. Bibcode:2012NatSR...2E.960R. doi:10.1038/srep00960. PMC3518813. PMID 23233879.
^Chirgwin, Richard (12 December 2012). "Dying to make greener batteries". The Register. Retrieved 12 December 2012.
April 08, 2024
trihydroxyanthraquinone, commonly, called, purpurin, anthraquinone, naturally, occurring, yellow, formally, derived, from, anthraquinone, replacement, three, hydrogen, atoms, hydroxyl, groups, namespreferred, iupac, name, trihydroxyanthracene, dioneother, name. 1 2 4 Trihydroxyanthraquinone commonly called purpurin is an anthraquinone It is a naturally occurring red yellow dye It is formally derived from 9 10 anthraquinone by replacement of three hydrogen atoms by hydroxyl OH groups 1 2 4 Trihydroxyanthraquinone NamesPreferred IUPAC name 1 2 4 Trihydroxyanthracene 9 10 dioneOther names Purpurin Purpurine Hydroxylizaric acidIdentifiersCAS Number 81 54 9 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 8645 YChEMBL ChEMBL294264 YChemSpider 6431 YECHA InfoCard 100 001 237KEGG C10395 YPubChem CID 6683UNII L1GT81LS6N YCompTox Dashboard EPA DTXSID4021214InChI InChI 1S C14H8O5 c15 8 5 9 16 14 19 11 10 8 12 17 6 3 1 2 4 7 6 13 11 18 h1 5 15 16 19H YKey BBNQQADTFFCFGB UHFFFAOYSA N YInChI 1 C14H8O5 c15 8 5 9 16 14 19 11 10 8 12 17 6 3 1 2 4 7 6 13 11 18 h1 5 15 16 19HKey BBNQQADTFFCFGB UHFFFAOYAWSMILES C1 CC C2C C1 C O C3 C C2 O C C C C3O O OO C2c1ccccc1C O c3c2c O cc O c3OPropertiesChemical formula C14H8O5Molar mass 256 21 g molMelting point 259 C 498 F 532 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Purpurin is also called verantin smoke Brown G hydroxylizaric acid and C I 58205 It is a minor component of the classical lake pigment madder lake or Rose Madder Contents 1 History 2 Natural occurrence 3 Properties 4 Uses 5 See also 6 ReferencesHistory editMadder root has been used for dying cloth at least since 1500 BC 2 Purpurin and alizarin were isolated from the root by Pierre Robiquet and Colin two French chemists in 1826 They were identified as anthracene derivatives by Grabe and Liebermann in 1868 They also synthesized alizarin from bromoanthraquinone which together with the conversion of alizarin into purpurin published previously by M F De Lalande provided the first synthetic route to purpurin 3 The positions of the OH groups were determined by Bayer and Caro in 1874 1875 4 Natural occurrence editPurpurin occurs in the roots of the madder plant Rubia tinctorum together with alizarin 1 2 dihydroxyanthraquinone The root actually contains colorless glycosides of the dyes Properties editPurpurin is a crystalline solid that forms orange red needles melting at 259 C 498 F 1 It becomes red when dissolved in ethanol and yellow when dissolved with alkalis in boiling water It is insoluble in hexane but soluble in chloroform and can be obtained from chloroform as reddish needles 5 Unlike alizarin purpurin is dissolved by boiling in a solution of aluminium sulfate from which it can be precipitated by acid This procedure can be used to separate the two dyes 6 Like many dihydroxy and trihydroxyanthraquinones pupurin has a purgative action although only 1 20 as effective as 1 2 7 trihydroxyanthraquinone anthrapurpurin 7 Uses editPurpurin is a fast dye for cotton printing and forms complexes with various metal ions It fades faster than alizarin on exposure to sunlight 2 A study published in Nature journal Scientific Reports suggests that the purpurin could replace cobalt in lithium ion batteries 8 Eliminating cobalt would mean eliminating a hazardous material allow batteries to be produced at room temperature and lower the cost of recycling batteries Extracting purpurin from farmed madder is a simple task alternately the chemical could be synthesized in a lab 9 See also editTrihydroxyanthraquinone Pierre Robiquet discoverer of purpurin in 1826References edit a b Haynes William M ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press p 3 530 ISBN 9781498754293 a b Madder Root Archived 2011 07 14 at the Wayback Machine catalog entry at Natural Pigments website Accessed on 2010 01 22 Chemical news and journal of industrial science Volume 30 Page 207 Wahl Andre Atack F W 1919 The Manufacture Of Organic Dyestuffs G Bell And Sons Limited Online version accessed on 2010 01 22 Vankar Padma S Shanker Rakhi Mahanta Debajit Tiwari S C 2008 Ecofriendly sonicator dyeing of cotton with Rubia cordifolia Linn using biomordant Dyes and Pigments 76 1 207 212 doi 10 1016 j dyepig 2006 08 023 Irving Wetherbee Fay 1919 The chemistry of the coal tar dyes Van Nostrand Online version accessed on 2010 01 22 Alister McGuigan Hugh 1921 An introduction to chemical pharmacology pharmacodynamics in relation to chemistry P Blakiston s son Philadelphia Reddy Arava Leela Mohana Nagarajan Subbiah Chumyim Porramate Gowda Sanketh R Pradhan Padmanava Jadhav Swapnil R Dubey Madan John George Ajayan Pulickel M Ajayan Pulickel M 2012 Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes Scientific Reports 2 960 Bibcode 2012NatSR 2E 960R doi 10 1038 srep00960 PMC 3518813 PMID 23233879 Chirgwin Richard 12 December 2012 Dying to make greener batteries The Register Retrieved 12 December 2012 Retrieved from https en wikipedia org w index php title 1 2 4 Trihydroxyanthraquinone amp oldid 1149765103, wikipedia, wiki, book, books, library,
