Synthesis of Alizarin Red S

Preparation of Alizarin Red S

Preparation of Alizarin Red S

Preparation of Alizarin Red S

25 g of alizarin and 150 g of oleum containing 20% of SO3 were mixed in a porcelain beaker and heated in an oil bath at 140-150  C°. The heating is continued until the sample from the reaction mass will not completely dissolve in water. Then the reaction mixture is poured into 500-750 ml of water and filtered. The clear filtrate with good stirring is treated with lead carbonate until carbon dioxide evolution ceases. Lead sulfate is filtered and -SO4-2 ions are separated gently with lead acetate solution. The solution is filtered and saturated with hydrogen sulfide. PbS is filtered and the filtrate is evaporated to dryness on a water bath. The resulting residue is dissolved in 50-75 ml of water and filtered off unreacted alizarin.In order to  completely remove unreacted alizarin the filtrate is shaken in a separatory funnel with ether. The aqueous layer is separated and evaporated on a water bath to a small volume and saturated sodium chloride. The liquid is left for a day to cool, filtered and the sodium salt (Alizarin Red S ) is recrystallized from ethanol. Alizarin Red S forms the orange-yellow powder, soluble in water and alcohol. Insoluble in ether.

Л.М. Кульберг, Синтезы органических реактивов для неорганического анализа, 11, (1947) (LM Koulberg, Synthesis of organic reagents for inorganic analysis, 11, (1947))

IUPAC Name

sodium;3,4-dihydroxy-9,10-dioxoanthracene-2-sulfonate

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

InChI Key

HFVAFDPGUJEFBQ-UHFFFAOYSA-M

Canonical SMILES

C1=CC=C2C(=C1)C(=O)C3=CC(=C(C(=C3C2=O)O)O)S(=O)(=O)[O-].[Na+]

MeSH Synonyms

Alizarin Red S, Alizarin Red S, monosodium salt, Alizarine S, alizarine sulfonate

Depositor-Supplied Synonyms

Alizarin Red S, 130-22-3, sodium 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, Mordant Red 3, Sodium alizarinesulfonate, Alizarin Carmine, Alizarine S, Sodium alizarinsulfonate, Acid Red Alizarine, alizarine carmine, C.I. 58005, Sodium alizarin-3-sulfonate, Alizarine Red S sodium salt, Alizarinsulfonate, Alizarin S, Alizarin-3-sulfonate sodium salt, Alizarine Red A, Alizarine Red W, Fenakrom Red W, Diamond Red W, Alizarine Red AS, Alizarine Red SW, Alizarine Red SZ, Alizarine Red WA, Alizarine Red WS, Ahcoquinone Red S, Alizarinrot-S [German], Alizarin sulfonate sodium, Carnelio Rubine Lake, Chrome Red Alizarine, Oxanal Fast Red SW, Alizarin Red, water soluble, Alizarin sodium monosulfonate, Ext D and C Red No. 7, Alizarine Red Indicator, Alizarine Red For Wool, Mitsui Alizarine Red S, C.I. Mordant Red 3, Alizarinsulfonic acid sodium salt, CHEBI:87358, Sodium 3,4-dihydroxyanthraquinone-2-sulfonate, Alizarine S Extra Pure A, Alizarine Carmine Indicator, Alizarine S Extra Conc. A Export, Alizarin Carmine (biological stain), Alizarine Red S (biological stain), Calcochrome Alizarine Red SC, EINECS 204-981-8, Alizarine Carmine (Biological stain), NSC 56653, STK076707, ST055357, 9,10-Dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid monosodium salt, sodium 3,4-dihydroxy-9,10-dioxoanthracene-2-sulfonate, 2-Anthraquinonesulfonic acid, 3,4-dihydroxy-, sodium salt, 3,4-Dihydroxy-9,10-dioxo-2-anthracenesulfonic acid sodium salt, CHEMBL175336, 2-Anthracenesulfonic acid, 9,10-dihydro-3,4-dihydroxy-9,10-dioxo-, monosodium salt, 2-Anthracenesulfonic acid, 9,10-dihydro-3,4-dihydroxy-9,10-dioxo-, sodium salt (1:1), Sodium 9,10-dihydro-3,4-dihydroxy-9,10-dioxoanthracene-2-sulphonate monohydrate, 3,4-dihydroxy-9,10-dioxoanthracene-2-sulfonic acid, sodium salt, Alizarinrot-S, UcEO>>CEaAAE, UcEO>>CEa AAENI, UcEO S AAE, UcEOeUO not masculinei, Alizarin sodium sulfonate, AC1Q1HJB, C14H7NaO7S, AC1N00NK, E(R)EUEthOUcEO masculinei, UNII-3F3AT0Q12H, 83-61-4 (Parent), SCHEMBL728494, 3F3AT0Q12H, A5533_SIAL, MolPort-002-136-077, MolPort-002-941-680, MolPort-009-752-638, Alizarin Red S (C.I. 58005), AR-1H6724, MFCD00013049, SBB005411, STL445507, AKOS004901450, AKOS015903821, AKOS024282311, AK116532, L935, LS-20381, PL006626, PL043964, KB-259797, FT-0621968, ST24031634, EN300-92948, Z-0090, I14-18022, potassium 3,4-dihydroxy-9,10-dioxoanthracene-2-sulfonate, 3,4- paragraph signthornoC>>u-9,10- paragraph signthornNo u-2-Yi>>CEa AAENI, 12777-35-4, 63309-95-5

Removed Synonyms

Alizarin, CID8533, CID3955344, T1761, 89125-21-3

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *