ALIZARIN RED S

Alizarin Red S
Names
	IUPAC name 3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
	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 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:87358;
ChemSpider	8217;
ECHA InfoCard	100.004.530
EC Number	204-981-8;
PubChem CID	3955344;
UNII	3F3AT0Q12H ;
CompTox Dashboard ( EPA)	DTXSID0052679 ;
	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

Alizarin Red S (also known as C.I. Mordant Red 3, Alizarin Carmine, and C.I 58005.^[1]) is a water-soluble sodium salt of Alizarin sulfonic acid with a chemical formula of C
₁₄H
₇NaO
₇S.^[2]^[1] Alizarin Red S was discovered by Graebe and Libermann in 1871.^[2] In the field of histology alizarin Red S is used to stain calcium deposits in tissues,^[3]^[4] and in geology to stain and differentiate carbonate minerals.^[3]

Uses

Alizarin Red S is used in histology and 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 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 alizarin Red S has been used to mark daily growth layers.^[5]

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

References

^ ^a ^b ^c Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.
^ ^a ^b Legan, Lea; Retko, Klara; Ropret, Polonca (2016). "Vibrational spectroscopic study on degradation of alizarin carmine". Microchemical Journal. 127: 36–45. doi: 10.1016/j.microc.2016.02.002. ISSN 0026-265X.
^ ^a ^b ^c Puchtler, Holde; Meloan, Susan N.; Terry, Mary S. (1969). "On the history and mechanism of alizarin and alizarin red S stains for calcium". Journal of Histochemistry & Cytochemistry. 17 (2): 110–124. doi: 10.1177/17.2.110. ISSN 0022-1554. PMID 4179464.
^ ^a ^b ^c ^d Bancroft, John; Stevens, Alan, eds. (1982). The Theory and Practice of Histological Techniques (2nd ed.). Longman Group Limited.
^ Holcomb, Michael; Cohen, Anne L.; McCorkle, Daniel C. (2013). "An evaluation of staining techniques for marking daily growth in scleractinian corals" (PDF). Journal of Experimental Marine Biology and Ecology. 440: 126–131. doi: 10.1016/j.jembe.2012.12.003. hdl: 1912/5857. ISSN 0022-0981.
^ Dickson, J. A. D. (1966). "Carbonate identification and genesis as revealed by staining". Journal of Sedimentary Research. 36 (4): 491–505. doi: 10.1306/74D714F6-2B21-11D7-8648000102C1865D.

[Lillie,_1977-1] Lillie, Ralph Dougall (1977). H. J. Conn's Biological stains (9th ed.). Baltimore: Williams & Wilkins. pp. 692p.

[Legan_et_al.,_2016-2] Legan, Lea; Retko, Klara; Ropret, Polonca (2016). "Vibrational spectroscopic study on degradation of alizarin carmine". Microchemical Journal. 127: 36–45. doi: 10.1016/j.microc.2016.02.002. ISSN 0026-265X.

[Puchtler_et_al.,_1969-3] Puchtler, Holde; Meloan, Susan N.; Terry, Mary S. (1969). "On the history and mechanism of alizarin and alizarin red S stains for calcium". Journal of Histochemistry & Cytochemistry. 17 (2): 110–124. doi: 10.1177/17.2.110. ISSN 0022-1554. PMID 4179464.

[Bancroft_and_Stevens,_1982-4] Bancroft, John; Stevens, Alan, eds. (1982). The Theory and Practice of Histological Techniques (2nd ed.). Longman Group Limited.

[Holcomb_et_al.,_2013-5] Holcomb, Michael; Cohen, Anne L.; McCorkle, Daniel C. (2013). "An evaluation of staining techniques for marking daily growth in scleractinian corals" (PDF). Journal of Experimental Marine Biology and Ecology. 440: 126–131. doi: 10.1016/j.jembe.2012.12.003. hdl: 1912/5857. ISSN 0022-0981.

[Dickson,_1966-6] Dickson, J. A. D. (1966). "Carbonate identification and genesis as revealed by staining". Journal of Sedimentary Research. 36 (4): 491–505. doi: 10.1306/74D714F6-2B21-11D7-8648000102C1865D.

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[3]

[4]

[5]

[6]

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
Misc:	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 Leheria 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

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
Misc:	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

Uses

See also

References

Uses

See also

References

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Names

IUPAC name 3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
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
ChemSpider	8217
ECHA InfoCard	100.004.530
EC Number	204-981-8
PubChem CID	3955344
UNII	3F3AT0Q12H^Y
CompTox Dashboard ( EPA)	DTXSID0052679
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