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Revision as of 05:16, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 474899983 of page Alizarin for the Chem/Drugbox validation project (updated: '').		Latest revision as of 02:02, 19 July 2024 edit 38.49.72.163 (talk) rmv peacockish and instructional "notable" per MOS:PEA and MOS:NOTETags: Mobile edit Mobile web edit
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			{{short description|Chemical compound and histologic stain}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{redirect|Madder lake|the Australian band|Madder Lake (band)}}
	{{chembox		{{chembox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 443375249		| verifiedrevid = 477317635
	| Name = Alizarin		| Name = Alizarin
	| ImageFile1_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
			| ImageFile = Alizarin sublimed crop.jpg
	| ImageFile1 = Alizaryna.svg
			| ImageFile1 = Alizarin molecule ball from xtal.png
	| ImageName1 = Skeletal formula of alizarin
			| ImageName1 = Ball-and-stick model of alizarin
	| ImageFile2 = Alizarin-3D-balls.png
			| PIN = 1,2-Dihydroxyanthracene-9,10-dione
	| ImageName2 = Ball-and-stick model of alizarin
			| OtherNames = 1,2-Dihydroxy-9,10-anthracenedione<ref name=crc/><br />1,2-Dihydroxyanthraquinone<br />Turkey red<br />Mordant red 11<br />Alizarin B<br />Alizarin red
	| ImageFile3 = Alizarin-sample.jpg
			|Section1={{Chembox Identifiers
	| ImageSize3 = 160px
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ImageName3 = Sample of alizarin
	| IUPACName = 1,2-dihydroxy-9,10-anthracenedione
	| OtherNames = 1,2-Dihydroxyanthraquinone, Turkey red, Mordant red 11, Alizarin B, Alizarin red
	| Section1 = {{Chembox Identifiers
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 16866		| ChEBI = 16866
	| SMILES = O=C2c1ccccc1C(=O)c3c2ccc(O)c3O		| SMILES = O=C2c1ccccc1C(=O)c3c2ccc(O)c3O
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 60MEW57T9G		| UNII = 60MEW57T9G
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
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	| CASNo = 72-48-0		| CASNo = 72-48-0
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID=6056		| ChemSpiderID =6056
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| RTECS =		| RTECS =
			| 3DMet = B00298
			| Gmelin = 34541
			| Beilstein = 1914037
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 14 | H = 8 | O = 4		| C=14 | H=8 | O=4
	| Appearance = orange-red crystals or powder		| Appearance = orange-red crystals or powder
	| Density = 1.540 g/cm<sup>3</sup>		| Density = 1.540 g/cm<sup>3</sup>
	| Solubility = slightly to sparingly soluble		| Solubility = slightly to sparingly soluble
			| MeltingPtC = 289.5
	| MeltingPt = 279–83 °C
			| MeltingPt_ref =<ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293|page=3.10}}</ref>
	| BoilingPt = 430 °C
	| pKa = 6.94		| BoilingPtC = 430
			| BoilingPt_notes =
			| pKa = 6.94
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| RPhrases = {{R36}} {{R37}} {{R38}}		| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
	| SPhrases = {{S26}} {{S36}}
			| HPhrases = {{H-phrases|302|315|319}}
			| PPhrases = {{P-phrases|264|270|280|301+312|302+352|305+351+338|321|330|332+313|337+313|362|501}}
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherCpds = ], ]		| OtherCompounds = ], ]
	}}		}}
	}}		}}
			'''Alizarin''' (also known as '''1,2-dihydroxyanthraquinone''', '''Mordant Red 11''', ] '''58000''', and '''Turkey Red'''<ref></ref>) is an ] with formula {{chem|C|14|H|8|O|4}} that has been used throughout history as a red ], principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the ] genus.<ref name=vankar>The primary madder species from which alizarin historically has been obtained is '']''. See also {{ cite journal |author1=Vankar, P. S. |author2=Shanker, R. |author3=Mahanta, D. |author4=Tiwari, 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> In 1869, it became the first natural dye to be produced synthetically.<ref name=Ull/>
			Alizarin is the main ingredient for the manufacture of the madder ] known to painters as ] and ]. 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 use of alizarin in modern times is as a ] agent in biological research because it stains free ] and certain calcium compounds a red or light purple color. Alizarin continues to be used commercially as a red textile dye, but to a lesser extent than in the past.
			==History==
			Madder has been cultivated as a ] since antiquity in central ] and ], where it was grown as early as 1500 BC. Cloth dyed with madder root pigment was found in the tomb of the ] ],<ref>{{cite journal |last=Pfister |first=R. |date=December 1937 |title=Les Textiles du Tombeau de Toutankhamon |trans-title=Textiles of Tutankhamun's Tomb |url=https://www.jstor.org/stable/43475067 |url-access=limited |language=French |journal=Revue des arts asiatiques |volume=11 |issue=4 |pages=209 |jstor=43475067 |access-date=February 13, 2021}}</ref> in the ruins of ]{{citation needed|date=March 2012}}, and ancient ] and ].<ref>{{cite journal |last=Farnsworth |first=Marie |date=July 1951 |title=Second Century B. C. Rose Madder from Corinth and Athens |url=https://www.jstor.org/stable/500972 |url-access=limited |journal=American Journal of Archaeology |volume=55 |issue=3 |pages=236–239 |doi=10.2307/500972 |jstor=500972 |access-date=February 13, 2021}}</ref> In the Middle Ages, ] encouraged madder cultivation. Madder was widely used as a dye in Western Europe in the Late Medieval centuries.<ref>Many examples of the use of the word "madder", meaning the roots of the plant ''Rubia tinctorum'' used as a dye, are given in the , a dictionary of late medieval English.</ref> In 17th century England, alizarin was used as a red dye for the clothing of the parliamentary ]. The distinctive red color would continue to be worn for centuries (though also produced by other dyes such as ]), giving English and later British soldiers the nickname of "]".
			] ]]
			The madder dyestuff is combined with a dye ]. Depending on which mordant is used, the resulting color may be anywhere from pink through purple to dark brown. In the 18th century, the most valued color was a bright red known as "Turkey Red". The combination of mordants and overall technique used to obtain the Turkey Red originated in the Middle East or Turkey (hence the name). It was a complex and multi-step technique in its Middle Eastern formulation, some parts of which were unnecessary.<ref>{{ cite book | author = Lowengard, S. | year = 2006 | chapter = Industry and Ideas: Turkey Red | title = The Creation of Color in 18th Century Europe | publisher = Gutenberg-E.org | isbn = 9780231503693 | chapter-url = http://www.gutenberg-e.org/lowengard/C_Chap36.html }} Additional 18th century history at {{ cite web | url = http://www.colorantshistory.org/TurkeyRed.html | title = Turkey Red Dyeing in Blackley - The Delaunay Dyeworks | publisher = ColorantsInHistory.org }}</ref> The process was simplified in late 18th-century Europe. By 1804, dye maker ] in Britain had refined a technique to make '']'' madder by treating it with ], and an ],<ref>George Field's notes are held at the Courtauld Institute of Art. See {{cite web | url = http://www.aim25.ac.uk/cgi-bin/search2?coll_id=4107&inst_id=2 | title = FIELD, George (?1777–1854) | access-date = 2012-08-04 | archive-date = 2008-10-17 | archive-url = https://web.archive.org/web/20081017134954/http://www.aim25.ac.uk/cgi-bin/search2?coll_id=4107&inst_id=2 | url-status = dead }}</ref> that converts the water-soluble madder extract into a solid, insoluble pigment. This resulting ''madder lake'' has a longer-lasting color, and can be used more efficaciously, for example by blending it into a ]. Over the following years, it was found that other metal salts, including those containing ], ], and ], could be used in place of alum to give madder-based pigments of various other colors. This general method of preparing lakes has been known for centuries<ref>{{cite book | author = Thompson, D. V. | title = The Materials and Techniques of Medieval Painting | year = 1956 | publisher = Dover | pages = | isbn = 978-0-486-20327-0 | url-access = registration | url = https://archive.org/details/materialstechniq00thom/page/115 }}</ref> but was simplified in the late 18th and early 19th centuries.
			In 1826, the ] chemist ] found that madder root contained two colorants, the red alizarin and the more rapidly fading ].<ref>See:
			* Pierre-Jean Robiquet and Jean-Jacques Colin (1826) (On a new substance from plants (alizarin) obtained from madder), ''Journal de pharmacie et des sciences accessoires'', 2nd series, '''12''' : 407–412.
			* Jean-Jacques Colin and Pierre-Jean Robiquet (1827) (New research into the coloring material of madder), ''Annales de chimie et de physique'', 2nd series, '''34''' : 225–253.</ref> The alizarin component became the first natural dye to be synthetically duplicated in 1868 when the ] chemists ] and ], working for ], found a way to produce it from ].<ref>Note:
			* In 1868, Graebe and Liebermann showed that alizarin can be converted into anthracene. See: C. Graebe and C. Liebermann (1868) (On alizarin and anthracene), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', '''1''' : 49–51.
			* In 1869, Graebe and Liebermann announced that they had succeeded in transforming anthracene into alizarin. See: C. Graebe and C. Liebermann (1869) (On the artificial formation of alizarin), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', '''2''' : 14.
			* For Graebe and Liebermann's original process for making alizarin from anthracene, see: Charles Graebe and Charles Liebermann, U.S. Patent no. 95,465 (issued: October 5, 1869). (See also their English patent, no. 3,850, issued December 18, 1868.)
			* A more efficient process for making alizarin from anthracene was developed by Caro, Graebe and Liebermann in 1870. See: H. Caro, C. Graebe, and C. Liebermann (1870) (On the manufacture of artificial alizarin), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', '''3''' : 359–360.</ref> The ] company draws its roots from alizarin as well.<ref name="bayereh">{{cite news |title=History The Early Years (1863–1881) |url=https://www.bayer.com/en/history/1863-1881 |access-date=4 February 2021 |publisher=Bayer AG}}</ref> About the same time, the ] dye chemist ] independently discovered the same synthesis, although the BASF group filed their patent before Perkin by one day. The subsequent discovery (made by Broenner and Gutzhow in 1871) that anthracene could be abstracted from ] further advanced the importance and affordability of alizarin's artificial synthesis.<ref>{{ cite journal |author1=Brönner, J. |author2=Gutzkow, H. | title = Verfahren zur Darstellung von Anthracen aus dem Pech von Steinkohlentheer, und zur Darstellung von Farbstoffen aus Anthracen |trans-title=Process for Preparing Anthracene from Coal-Tar Pitch, and Preparation of Dye-Stuffs from Anthracene | language = de | journal = Dinglers Polytechnisches Journal | year = 1871 | volume = 201 | pages = 545–546 | url = https://books.google.com/books?id=QRQ1AAAAMAAJ&pg=PA545 }}</ref>
			The synthetic alizarin could be produced for a fraction of the cost of the natural product, and the market for madder collapsed virtually overnight. The principal synthesis entailed bromination of anthraquinone by bromine (in a sealed tube at 100 <sup>o</sup>C) to give 1,2-dibromoanthraquinone. Then the two bromine atoms were substituted by -OH by heating (170 <sup>o</sup>C) with KOH, followed by treatment with strong acid.<ref>{{Cite journal |last1=Graebe |first1=C. |last2=Liebermann |first2=C. |date=1869 |title=Ueber künstliches Alizarin |url=https://onlinelibrary.wiley.com/doi/10.1002/cber.186900201141 |journal=Berichte der Deutschen Chemischen Gesellschaft |language=en |volume=2 |issue=1 |pages=332–334 |doi=10.1002/cber.186900201141 |s2cid=96340805 |issn=0365-9496}}</ref> The incorporation of two bromine atoms in 1 and 2 position is not expected by an aromatic electrophilic substitution, and suggest the existence of an α,β unsaturated enol form of anthraquinone which suffer electrophilic addition by bromine.
			Alizarin, as a dye, has been largely replaced today by the more light-resistant ] pigments developed at ] in 1958.
			==Structure and properties==
			], is an isomer of alizarin.<ref name=Ull>{{ Ullmann | author = Bien, H.-S. | author2 = Stawitz, J. | author3 = Wunderlich, K. | title = Anthraquinone Dyes and Intermediates | doi = 10.1002/14356007.a02_355 }}</ref><ref>{{cite journal|journal=Org. Synth.|year=1926|volume=6|page=78|doi=10.15227/orgsyn.006.0078|title=Quinizarin|first1=L. A.|last1=Bigelow|first2=H. H.|last2=Reynolds}}</ref>]]
			Alizarin is one of ten ] isomers. It is soluble in ] and ], and can be obtained from the latter as red-purple crystals, melting point 277–278&nbsp;°C.<!--Vis λ<sub>max</sub> (MeOH) (nm): 431, UV λ<sub>max</sub> (MeOH) (nm): 245, 260, 271, 331; IR ν<sub>max</sub> (KBr) (cm<sup>−1</sup>): 3338 (-OH), 1662, 1628 (-C=O), 1580 (aromatic -C=C-); MS: ''m''/''z'' 240 (M<sup>+</sup>).--><ref name=vankar/>
			Alizarin changes color depending on the pH of the solution it is in, thereby making it a ].<ref>{{ cite journal |author1=Meloan, S. N. |author2=Puchtler, H. |author3=Valentine, L. S. | title = Alkaline and Acid Alizarin Red S Stains for Alkali-Soluble and Alkali-Insoluble Calcium Deposits | journal = Archives of Pathology | year = 1972 | volume = 93 | issue = 3 | pages = 190–197 | pmid = 4110754 }}</ref>
			==Applications==
			Alizarin Red is used in a biochemical assay to determine, quantitatively by ], the presence of calcific deposition by cells of an ] lineage. As such it is an early stage marker (days 10–16 of in vitro culture) of matrix mineralization, a crucial step towards the formation of calcified ] associated with true bone.{{Citation needed|date=July 2010}}
			Alizarin's abilities as a biological stain were first noted in 1567, when it was observed that when fed to animals, it stained their teeth and bones red. The chemical is now commonly used in medical studies involving calcium. Free (ionic) calcium forms precipitates with alizarin, and tissue block containing calcium stain red immediately when immersed in alizarin. Thus, both pure calcium and calcium in bones and other tissues can be stained. These alizarin-stained elements can be better visualized under fluorescent lights, excited by 440–460 nm.<ref>{{Cite journal|last1=Smith|first1=W. Leo|last2=Buck|first2=Chesney A.|last3=Ornay|first3=Gregory S.|last4=Davis|first4=Matthew P.|last5=Martin|first5=Rene P.|last6=Gibson|first6=Sarah Z.|last7=Girard|first7=Matthew G.|date=2018-08-20|title=Improving Vertebrate Skeleton Images: Fluorescence and the Non-Permanent Mounting of Cleared-and-Stained Specimens|journal=Copeia|language=en-US|volume=106|issue=3|pages=427–435|doi=10.1643/cg-18-047|issn=0045-8511|doi-access=free}}</ref> The process of staining calcium with alizarin works best when conducted in acidic solution (in many labs, it works better in pH 4.1 to 4.3).<ref name=puchtler>{{ cite journal |author1=Puchtler, H. |author2=Meloan, S. N. |author3=Terry, M. S. | title = On the History and Mechanism of Alizarin Red S Stains for Calcium | journal = The Journal of Histochemistry and Cytochemistry | year = 1969 | volume = 17 | issue = 2 | pages = 110–124 | pmid = 4179464 | doi=10.1177/17.2.110| doi-access = free }}</ref>
			In clinical practice, it is used to stain ] to assess for basic ] crystals.<ref>{{ cite journal |author1=Paul, H. |author2=Reginato, A. J. |author3=Schumacher, H. R. | title = Alizarin Red S Staining as a Screening Test to Detect Calcium Compounds in Synovial Fluid | journal = Arthritis and Rheumatism | year = 1983 | volume = 26 | issue = 2 | pages = 191–200 | pmid = 6186260 | doi=10.1002/art.1780260211| doi-access = free }}</ref> Alizarin has also been used in studies involving bone growth, osteoporosis, bone marrow, calcium deposits in the vascular system, cellular signaling, gene expression, tissue engineering, and mesenchymal stem cells.<ref name=puchtler/>
			In ], it is used as a stain to differentiate the ] ], especially ] and ] in ] or polished surfaces.<ref>{{Cite book | last = Green | first = O. R. | title = A Manual of Practical Laboratory and Field Techniques in Palaeobiology | publisher = Springer | year = 2001 | page = 56 | url = https://books.google.com/books?id=4lJr5LwvnX8C | isbn = 978-0-412-58980-5 }}</ref><ref name="Dickson, 1966">{{cite journal |last1=Dickson |first1=J. A. D. |title=Carbonate identification and genesis as revealed by staining |journal=Journal of Sedimentary Research |date=1966 |volume=36 |issue=4 |pages=491–505 |doi=10.1306/74D714F6-2B21-11D7-8648000102C1865D}}</ref>
			Madder lake had been in use as a red pigment in paintings since antiquity.<ref>Schweppe, H., and Winter, J. Madder and Alizarin in Artists’ Pigments. A Handbook of Their History and Characteristics, Vol 3: E.W. Fitzhugh (Ed.) Oxford University Press 1997, p. 111 – 112</ref>
			<gallery widths="200px" heights="200px">
			File:Red alizarin 1.jpg|Red alizarin staining of rat's embryonic bones for osteogenesis study
			File:N pectoralis.jpg|Red alizarin stained juvenile ] lit by fluorescent light. <ref>{{Cite journal|last1=Smith|first1=W. Leo|last2=Buck|first2=Chesney A.|last3=Ornay|first3=Gregory S.|last4=Davis|first4=Matthew P.|last5=Martin|first5=Rene P.|last6=Gibson|first6=Sarah Z.|last7=Girard|first7=Matthew G.|date=2018-08-20|title=Improving Vertebrate Skeleton Images: Fluorescence and the Non-Permanent Mounting of Cleared-and-Stained Specimens|journal=Copeia|language=en-US|volume=106|issue=3|pages=427–435|doi=10.1643/cg-18-047|s2cid=91688529 |issn=0045-8511}}</ref>
			File:Johannes (Jan) Vermeer - Christ in the House of Martha and Mary - Google Art Project.jpg|Johannes Vermeer, Christ in the House of Martha and Mary, 1654-56. The red jacket worn by Mary is painted in madder lake
			File:Walraversijde18.jpg|Reconstruction blankets dyed with madder
			</gallery>
			==See also==
			* ] or purpurin, another red dye that occurs in madder root
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			*]
			* ]
			==References==
			{{Reflist}}
			== Further reading ==
			* Schweppe, H., and Winter, J. "Madder and Alizarin", in ''Artists’ Pigments: A Handbook of Their History and Characteristics, Vol. 3'': E.W. Fitzhugh (Ed.) Oxford University Press 1997, pp. 109–142
			==External links==
			{{Commonscat}}
			*
			* , Colourlex
			{{Anthraquinone}}
			{{Authority control}}
			]
			]
			]
			]
			]
			]