Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,2,4-Trihydroxyanthraquinone: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477202730

| ImageFile = Purpurin powder crop.jpg

| ImageFile1 = 1,2,4-trihydroxyanthracene-9,10-dione 200.svg

| ImageName1 = Skeletal formula

| ImageFile2 = Purpurin-3D-balls.png

| ImageName2 = Ball-and-stick model

| PIN = 1,2,4-Trihydroxyanthracene-9,10-dione

| OtherNames = Purpurin, Purpurine, Hydroxylizaric acid

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 81-54-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L1GT81LS6N

|Section2={{Chembox Properties

| Formula = C{{sub|14}}H{{sub|8}}O{{sub|5}}

| MeltingPt_ref = <ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293|page=3.530}}</ref>

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'''1,2,4-Trihydroxyanthraquinone''', commonly called '''purpurin''', is an [[natural anthraquinone|anthraquinone]]. It is a [[natural dye|naturally occurring red/yellow dye]]. It is formally derived from 9,10-[[anthraquinone]] by replacement of three [[hydrogen]] atoms by [[hydroxyl]] (OH) groups.

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|Rose Madder]].

== History ==

Madder root has been used for dying cloth at least since 1500 BC.<ref name=natpig>''[http://naturalpigments.com/detail.asp?PRODUCT_ID=455-22B Madder Root] {{Webarchive|url=https://web.archive.org/web/20110714160122/http://naturalpigments.com/detail.asp?PRODUCT_ID=455-22B |date=2011-07-14 }}'' catalog entry at Natural Pigments website. Accessed on 2010-01-22.</ref> Purpurin and alizarin were isolated from the root by [[Pierre Robiquet]] and [[Jean Jacques Colin|Colin]], two French chemists, in 1826. They were identified as anthracene derivatives by [[Carl Gräbe|Gräbe]] and [[Carl Theodore Liebermann|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.<ref>Chemical news and journal of industrial science, Volume 30, Page 207</ref> The positions of the OH groups were determined by [[Adolph Bäyer|Bayer]] and [[Heinrich Caro|Caro]] in 1874–1875.<ref>

Wahl, Andre; Atack, F. W (1919) ''The Manufacture Of Organic Dyestuffs''. G. Bell And Sons, Limited. [https://archive.org/stream/manufactureoforg031846mbp#page/n219 Online version] accessed on 2010-01-22.

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==Natural occurrence==

Purpurin occurs in the roots of the [[Rose madder|madder]] plant (''[[Rubia tinctorum]]''), together with [[alizarin]] (1,2-dihydroxyanthraquinone). The root actually contains colorless [[glycoside]]s of the dyes.

==Properties==

Purpurin is a [[crystalline]] solid, that forms orange-red needles melting at {{convert|259|C}}.<ref name=crc/> It becomes red when dissolved in [[ethanol]], and yellow when dissolved with [[alkali]]s in boiling water. It is insoluble in [[hexane]] but soluble in [[chloroform]], and can be obtained from chloroform as reddish needles.<!--m.p. 253–256 °C. Vis λ{{sub|max}} (MeOH) (nm): 485, 512; IR ν{{sub|max}} (KBr) (cm{{sup|−1}}): 3400 (-OH), 1675, 1650, 1630 (-C=O), 1594, 1585 (aromatic C=C); MS: ''m''/''z'' 256 (M{{sup|+}})--><ref name=vankar>{{cite journal | last1 = Vankar | first1 = Padma S. | last2 = Shanker | first2 = Rakhi | last3 = Mahanta | first3 = Debajit | last4 = Tiwari | first4 = S.C. | year = 2008 | title = Ecofriendly sonicator dyeing of cotton with ''Rubia cordifolia'' Linn. using biomordant | journal = Dyes and Pigments | volume = 76 | issue = 1| pages = 207–212 | doi = 10.1016/j.dyepig.2006.08.023 }}</ref> Unlike alizarin, purpurin is dissolved by boiling in a solution of [[aluminium sulfate]], from which it can be [[precipitate]]d by acid. This procedure can be used to separate the two dyes.<ref name=cotar>Irving Wetherbee Fay (1919) ''The chemistry of the coal-tar dyes''. Van Nostrand [https://archive.org/stream/chemistryofcoalt00fayirich#page/360 Online version] accessed on 2010-01-22.

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Like many dihydroxy- and trihydroxyanthraquinones, pupurin has a [[purgative]] action, although only 1/20 as effective as [[1,2,7-trihydroxyanthraquinone]] (anthrapurpurin).<ref name= guigan>Alister McGuigan, Hugh (1921) [https://archive.org/stream/introductiontoch00mcguuoft#page/132 ''An introduction to chemical pharmacology; pharmacodynamics in relation to chemistry'']. P. Blakiston's son, Philadelphia.

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==Uses==

Purpurin is a fast dye for [[cotton]] printing and forms complexes with various metal ions. It fades faster than alizarin on exposure to sunlight.<ref name=natpig/>

A study published in ''[[Nature (journal)|Nature]]'' journal ''Scientific Reports'' suggests that the purpurin could replace cobalt in [[lithium-ion batteries]].<ref>{{cite journal |last1=Reddy |first1=Arava Leela Mohana |last2=Nagarajan |first2=Subbiah |last3=Chumyim |first3=Porramate |last4=Gowda |first4=Sanketh R |last5=Pradhan |first5=Padmanava |last6=Jadhav |first6=Swapnil R |last7=Dubey |first7=Madan |last8=John |first8=George |last9=Ajayan |first9=Pulickel M |last10=Ajayan |first10=Pulickel M |year=2012 |title=Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes |journal=Scientific Reports |doi=10.1038/srep00960 |volume=2 |pages=960 |pmid=23233879 |pmc=3518813|bibcode=2012NatSR...2E.960R }}</ref> 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 [[Rubia tinctorum|madder]] is a simple task; alternately, the chemical could be synthesized in a lab.<ref>{{cite news |title=Dying to make greener batteries |author=Chirgwin, Richard |date=12 December 2012 |work=The Register |url=https://www.theregister.co.uk/2012/12/12/rose_madder_battery_matter/ |access-date=12 December 2012}}</ref>

==See also==

* [[Trihydroxyanthraquinone]]

* [[Pierre Robiquet]], discoverer of purpurin in 1826

==References==

{{reflist|30em}}

{{DEFAULTSORT:Trihydroxyanthraquinone, 1, 2, 4-}}

[[Category:Anthraquinone dyes]]

[[Category:Hydroxyquinols]]

[[Category:Trihydroxyanthraquinones]]