# Alizarin Red S

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Chemical compound and histologic dye

Alizarin Red S Names IUPAC name Sodium 3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate Other names Mordant Red 3 C.I 58005 Sodium alizarinesulfonate Alizarine S Alizarine sulfonate Alizarin Red, water-soluble Alizarin Carmine Alizarin sodium monosulfonate Identifiers CAS Number 130-22-3 Y 3D model (JSmol) Interactive image ChEBI CHEBI:87358 ChEMBL ChEMBL175336 ChemSpider 8217 ECHA InfoCard 100.004.530 EC Number 204-981-8 PubChem CID 3955344 UNII 3F3AT0Q12H Y CompTox Dashboard (EPA) DTXSID6052744 InChI InChI=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 Key: HFVAFDPGUJEFBQ-UHFFFAOYSA-M SMILES [Na+].Oc1c(O)c2C(=O)c3ccccc3C(=O)c2cc1S([O-])(=O)=O Properties Chemical formula C14H7NaO7S Molar mass 342.253 g/mol Appearance yellow-orange powder Solubility in water Soluble in water and ethanol Hazards Safety data sheet (SDS) [1] Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

**Alizarin Red S** (also known as [C.I.](/source/Colour_Index_International) **Mordant Red 3**, **Alizarin Carmine**, and C.I **58005**.[1]) is a water-soluble sodium [salt](/source/Salt_(chemistry)) of [Alizarin](/source/Alizarin) sulfonic acid with a [chemical formula](/source/Chemical_formula) of C 14H 7NaO 7S.[2][1] Alizarin Red S was discovered by [Graebe](/source/Carl_Gr%C3%A4be) and [Liebermann](/source/Carl_Theodore_Liebermann) in 1871.[2] In the field of [histology](/source/Histology) alizarin Red S is used to [stain](/source/Staining) [calcium](/source/Calcium) deposits in tissues,[3][4] and in [geology](/source/Geology) to stain and differentiate [carbonate minerals](/source/Carbonate_minerals).[3]

## Uses

Alizarin Red S, as sold for use as a histologic stain.

Alizarin Red S is used in histology and [histopathology](/source/Histopathology) to stain, or locate calcium deposits in tissues.[1][3][4] In the presence of calcium, Alizarin Red S, binds to the calcium to form a [Lake pigment](/source/Lake_pigment) that is orange to red in color.[4] Whole specimens can be stained with Alizarin Red S to show the distribution of bone, especially in developing embryos.[4] In living [corals](/source/Corals) alizarin Red S has been used to mark daily growth layers.[5]

In geology, Alizarin Red S is used on [thin sections](/source/Thin_section), and polished surfaces to help identify [carbonate minerals](/source/Carbonate_mineral) which stain at different rates.[6]

## See also

- [Aniline](/source/Aniline)

- [1,2,4-Trihydroxyanthraquinone](/source/1%2C2%2C4-Trihydroxyanthraquinone) or purpurin, another red dye that occurs in madder root

- [Hydroxyanthraquinone](/source/Hydroxyanthraquinone)

- [Dihydroxyanthraquinone](/source/Dihydroxyanthraquinone)

- [List of dyes](/source/List_of_dyes)

- [List of colors (compact)](/source/List_of_colors_(compact))

## References

1. ^ [***a***](#cite_ref-Lillie,_1977_1-0) [***b***](#cite_ref-Lillie,_1977_1-1) [***c***](#cite_ref-Lillie,_1977_1-2) Lillie, Ralph Dougall (1977). *H. J. Conn's Biological stains* (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.

1. ^ [***a***](#cite_ref-Legan_et_al.,_2016_2-0) [***b***](#cite_ref-Legan_et_al.,_2016_2-1) Legan, Lea; Retko, Klara; Ropret, Polonca (2016). "Vibrational spectroscopic study on degradation of alizarin carmine". *Microchemical Journal*. **127**: 36–45. [doi](/source/Doi_(identifier)):[10.1016/j.microc.2016.02.002](https://doi.org/10.1016%2Fj.microc.2016.02.002). [ISSN](/source/ISSN_(identifier)) [0026-265X](https://search.worldcat.org/issn/0026-265X).

1. ^ [***a***](#cite_ref-Puchtler_et_al.,_1969_3-0) [***b***](#cite_ref-Puchtler_et_al.,_1969_3-1) [***c***](#cite_ref-Puchtler_et_al.,_1969_3-2) Puchtler, Holde; Meloan, Susan N.; Terry, Mary S. (1969). ["On the history and mechanism of alizarin and alizarin red S stains for calcium"](https://doi.org/10.1177%2F17.2.110). *Journal of Histochemistry & Cytochemistry*. **17** (2): 110–124. [doi](/source/Doi_(identifier)):[10.1177/17.2.110](https://doi.org/10.1177%2F17.2.110). [ISSN](/source/ISSN_(identifier)) [0022-1554](https://search.worldcat.org/issn/0022-1554). [PMID](/source/PMID_(identifier)) [4179464](https://pubmed.ncbi.nlm.nih.gov/4179464).

1. ^ [***a***](#cite_ref-Bancroft_and_Stevens,_1982_4-0) [***b***](#cite_ref-Bancroft_and_Stevens,_1982_4-1) [***c***](#cite_ref-Bancroft_and_Stevens,_1982_4-2) [***d***](#cite_ref-Bancroft_and_Stevens,_1982_4-3) Bancroft, John; Stevens, Alan, eds. (1982). *The Theory and Practice of Histological Techniques* (2nd ed.). Longman Group Limited.

1. **[^](#cite_ref-Holcomb_et_al.,_2013_5-0)** Holcomb, Michael; Cohen, Anne L.; McCorkle, Daniel C. (2013). ["An evaluation of staining techniques for marking daily growth in scleractinian corals"](https://darchive.mblwhoilibrary.org/bitstream/1912/5857/1/dyepapsmjembe2.pdf) (PDF). *Journal of Experimental Marine Biology and Ecology*. **440**: 126–131. [Bibcode](/source/Bibcode_(identifier)):[2013JEMBE.440..126H](https://ui.adsabs.harvard.edu/abs/2013JEMBE.440..126H). [doi](/source/Doi_(identifier)):[10.1016/j.jembe.2012.12.003](https://doi.org/10.1016%2Fj.jembe.2012.12.003). [hdl](/source/Hdl_(identifier)):[1912/5857](https://hdl.handle.net/1912%2F5857). [ISSN](/source/ISSN_(identifier)) [0022-0981](https://search.worldcat.org/issn/0022-0981).

1. **[^](#cite_ref-Dickson,_1966_6-0)** Dickson, J. A. D. (1966). "Carbonate identification and genesis as revealed by staining". *Journal of Sedimentary Research*. **36** (4): 491–505. [doi](/source/Doi_(identifier)):[10.1306/74D714F6-2B21-11D7-8648000102C1865D](https://doi.org/10.1306%2F74D714F6-2B21-11D7-8648000102C1865D).

v t e Types of natural anthraquinones Dihydroxyanthraquinones Alizarin Aloe emodin Damnacanthal 1,3-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone Rhein Trihydroxyanthraquinones Parietin Emodin 1,2,4-Trihydroxyanthraquinone 1,3,8-Trihydroxyanthraquinone Tetrahydroxyanthraquinones quinalizarin rheoemodin Misc: Kermesic acid Carminic acid Senna glycosides

v t e Microbial and histological stains Iron/hemosiderin Perls Prussian blue Lipids Sudan stain Sudan II Sudan III Sudan IV Oil Red O Sudan Black B Carbohydrates Alcian blue Mucicarmine Periodic acid–Schiff stain Amyloid Congo red Thioflavin Bacteria Gram stain Methyl violet/Gentian violet Safranin Acid-fast Ziehl–Neelsen stain/Kinyoun stain Carbol fuchsin/Fuchsine Methylene blue Auramine–rhodamine stain Auramine O Rhodamine B Auramine phenol stain Connective tissue trichrome stain: Masson's trichrome stain/Lillie's trichrome Light Green SF yellowish Biebrich scarlet Phosphomolybdic acid Fast Green FCF Sirius Red Van Gieson's stain Other Cresyl violet Cyanine Jaswant Singh–Bhattacharji (JSB) stain H&E stain Haematoxylin Eosin Y Janus Green B Giemsa stain Gömöri trichrome stain Luxol fast blue stain Methyl blue Moeller stain Movat's stain Neutral red Schaeffer–Fulton stain Silver stain Bielschowsky stain Grocott's methenamine silver stain Warthin–Starry stain Wright's stain Tissue stainability Acidophilic Basophilic Chromophobic

v t e Dyeing Techniques Batik Dyeing Ikat Kasuri Kalamkari Katazome Leheriya Mordant Reactive dye printing Resist Ring dyeing Rōketsuzome Shibori Tie-dye Tsutsugaki Yūzen Types of dyes Dyes Natural Acid Reactive Solvent Substantive Sulfur Vat Disperse Discharge Pigment Traditional textile dyes Armenian cochineal Black walnut Bloodroot Brazilin Cochineal Cudbear Cutch Dyewoods Fustic Gamboge Dyer's broom Henna Indigo Kermes Logwood Madder Polish cochineal Saffron Turmeric Tyrian purple Weld Woad History Use of saffron Traditional dyes of the Scottish Highlands Craft dyes Dylon Inkodye Procion Rit Reference Glossary of dyeing terms List of dyes

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Adapted from the Wikipedia article [Alizarin Red S](https://en.wikipedia.org/wiki/Alizarin_Red_S) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Alizarin_Red_S?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.