Alizarin Red S

{{short description|Chemical compound and histologic dye}} {{Chembox  | ImageFile = Alizarin Red S.png | ImageSize = 270px | ImageAlt = Chemical structure of Alizarin Red S  | IUPACName = Sodium 3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate | OtherNames = {{Unbulleted list | Mordant Red 3 | C.I 58005 | Sodium alizarinesulfonate | Alizarine S | Alizarine sulfonate | Alizarin Red, water-soluble | Alizarin Carmine | Alizarin sodium monosulfonate }}  | Section1 = {{Chembox Identifiers | CASNo = 130-22-3 | CASNo_Ref = {{cascite|correct|CAS}} | ChEBI = 87358 | ChEMBL = 175336 | ChemSpiderID = 8217 | EC_number = 204-981-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3F3AT0Q12H | PubChem = 3955344 | StdInChI=1S/C14H8O7S.Na/c15-11-6-3-1-2-4-7(6)12(16)10-8(11)5-9(22(19,20)21)13(17)14(10)18;/h1-5,17-18H,(H,19,20,21);/q;+1/p-1 | StdInChIKey = HFVAFDPGUJEFBQ-UHFFFAOYSA-M | SMILES = [Na+].Oc1c(O)c2C(=O)c3ccccc3C(=O)c2cc1S([O-])(=O)=O }} | Section2 = {{Chembox Properties | Formula = C14H7NaO7S | MolarMass = 342.253 g/mol | Appearance = yellow-orange powder | Density = | MeltingPt = | BoilingPt = | Solubility = Soluble in water and ethanol }} | Section3 = {{Chembox Hazards | ExternalSDS = [https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=A5533&brand=SIAL&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Fsial%2Fa5533%3Flang%3Den] | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Alizarin Red S''' (also known as [[Colour Index International|C.I.]] '''Mordant Red 3''', '''Alizarin Carmine''', and C.I '''58005'''.<ref name="Lillie, 1977" />) is a water-soluble sodium [[salt (chemistry)|salt]] of [[Alizarin]] sulfonic acid with a [[chemical formula]] of {{chem|C|14|H|7|NaO|7|S}}.<ref name="Legan et al., 2016" /><ref name="Lillie, 1977" /> Alizarin Red S was discovered by [[Carl Gräbe|Graebe]] and [[Carl Theodore Liebermann|Liebermann]] in 1871.<ref name="Legan et al., 2016" /> In the field of [[histology]] alizarin Red S is used to [[staining|stain]] [[calcium]] deposits in tissues,<ref name="Puchtler et al., 1969" /><ref name="Bancroft and Stevens, 1982" /> and in [[geology]] to stain and differentiate [[carbonate minerals]].<ref name="Puchtler et al., 1969" />

==Uses== [[File:Alizarin_Red_S_powder_in_boat.jpg|thumb|left|upright=1|Alizarin Red S, as sold for use as a histologic stain.]] Alizarin Red S is used in histology and [[histopathology]] to stain, or locate calcium deposits in tissues.<ref name="Lillie, 1977" /><ref name="Puchtler et al., 1969" /><ref name="Bancroft and Stevens, 1982" /> In the presence of calcium, Alizarin Red S, binds to the calcium to form a [[Lake pigment]] that is orange to red in color.<ref name="Bancroft and Stevens, 1982" /> Whole specimens can be stained with Alizarin Red S to show the distribution of bone, especially in developing embryos.<ref name="Bancroft and Stevens, 1982" /> In living [[corals]] alizarin Red S has been used to mark daily growth layers.<ref name="Holcomb et al., 2013" />

In geology, Alizarin Red S is used on [[thin section]]s, and polished surfaces to help identify [[carbonate mineral]]s which stain at different rates.<ref name="Dickson, 1966" />

==See also== * [[Aniline]] * [[1,2,4-Trihydroxyanthraquinone]] or purpurin, another red dye that occurs in madder root * [[Hydroxyanthraquinone]] * [[Dihydroxyanthraquinone]] * [[List of dyes]] * [[List of colors (compact)]]

==References== {{Reflist|refs=

<ref name="Bancroft and Stevens, 1982">{{cite book |editor1-last=Bancroft |editor1-first=John |editor2-last=Stevens |editor2-first=Alan |title=The Theory and Practice of Histological Techniques |date=1982 |publisher=Longman Group Limited |edition=2nd}}</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>

<ref name="Holcomb et al., 2013">{{cite journal |last1=Holcomb |first1=Michael |last2=Cohen |first2=Anne L. |last3=McCorkle |first3=Daniel C. |title=An evaluation of staining techniques for marking daily growth in scleractinian corals |journal=Journal of Experimental Marine Biology and Ecology |volume=440 |year=2013 |pages=126–131 |issn=0022-0981 |doi=10.1016/j.jembe.2012.12.003 |bibcode=2013JEMBE.440..126H |hdl=1912/5857 |url=https://darchive.mblwhoilibrary.org/bitstream/1912/5857/1/dyepapsmjembe2.pdf |hdl-access=free}}</ref>

<ref name="Legan et al., 2016">{{cite journal |last1=Legan |first1=Lea |last2=Retko |first2=Klara |last3=Ropret |first3=Polonca |title=Vibrational spectroscopic study on degradation of alizarin carmine |journal=Microchemical Journal |volume=127 |year=2016 |pages=36–45 |issn=0026-265X |doi=10.1016/j.microc.2016.02.002}}</ref>

<ref name="Lillie, 1977">{{cite book |last1=Lillie |first1=Ralph Dougall |title=H. J. Conn's Biological stains |date=1977 |publisher=Williams & Wilkins |location=Baltimore |pages=692p |edition=9th}}</ref>

<ref name="Puchtler et al., 1969">{{cite journal |last1=Puchtler |first1=Holde |last2=Meloan |first2=Susan N. |last3=Terry |first3=Mary S. |title=On the history and mechanism of alizarin and alizarin red S stains for calcium |journal=Journal of Histochemistry & Cytochemistry |volume=17 |issue=2 |year=1969 |pages=110–124 |issn=0022-1554 |doi=10.1177/17.2.110 |pmid=4179464 |doi-access=free}}</ref>

}}

[[Category:Anthraquinone dyes]] [[Category:Catechols]] [[Category:Chelating agents]] [[Category:Dihydroxyanthraquinones]] [[Category:Organic pigments]] [[Category:Natural dyes]] [[Category:Staining dyes]] [[Category:Histology]] [[Category:Histotechnology]] [[Category:Histochemistry]]