130-22-3

Basic information

• Product Name: Alizarin Red S
• Synonyms: Alizarin Red S, certified, pure;ALIZARIN RED S SOLUTION 1% AQUEOUS;Alazarin red s.;dihydroxyanthraquinone-sulfonic acid sodium salt;ALIZARINSODIUMSULPHONATE;ALIZARINSODIUMSULPHATE;Alizarin Red S sodium salt, 1% w/v aq. sol.;Alizarine Red S (C.I. 58005)
• CAS NO: 130-22-3
• Molecular Formula: C₁₄H₇O₇S*Na
• Molecular Weight: 342.26
• EINECS: 204-981-8
• Product Categories: Dyes and Pigments;marker;Anthraquinone
• Mol File: 130-22-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: >250°C
• Boiling Point: 287-289°C
• Appearance: Various/Powder
• Storage Temp.: Store at +5°C to +30°C.
• Solubility: H2O: soluble1mg/mL
• PKA: 4.5, 11(at 25℃)
• Water Solubility: Soluble in water and alcohol.
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,8573
• BRN: 4117090
• CAS DataBase Reference: Alizarin Red S(CAS DataBase Reference)
• NIST Chemistry Reference: Alizarin Red S(130-22-3)
• EPA Substance Registry System: Alizarin Red S(130-22-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CB1095300
• TSCA: Yes
• Hazardous Substances Data: 130-22-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow-orange powder

Uses

Different sources of media describe the Uses of 130-22-3 differently. You can refer to the following data:
1. Alizarin Red S is used in the biochemical assay to determine the presence of calcium.
2. Alizarin Red S sodium salt is used as a chromogenic agent for the colorimetric determination of dothiepin hydrochloride in pharmaceutical formulations. It is also used as an ion-pair reagent for the spectrophotometric assay of fexofenadine in pharmaceuticals. It acts as a colorometric pH indicator in the range of 3.8-5.4. Further, it is used in a biochemical assay to determine the presence of calcific deposition by cells of an osteogenic lineage.

Definition

ChEBI: An organic sodium salt having 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate as the counterion. It is commonly used to stain embryo skeletons in cleared whole mounts, usually of small mammals.

Preparation

1,2-Dihydroxyanthracene-9,10-dione with fuming sulfuric acid sulphonate, and translated into Sodium salt.

Biochem/physiol Actions

Alizarin Red S is used for the staining of cartilage and bone. It reacts with calcium, thereby helping in the diagnosis of calcium deposits. It is also used to study carbohydrate–boronic acid interactions.

Properties and Applications

dark blue light red (chromium), brilliant yellow red (aluminum). Claybank powder. Soluble in Cellosolve, slightly soluble in ethanol and Acetone. In concentrated sulfuric acid to orange, dilution to pale yellow. Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water Alkali Acid ISO 3 6 4-5 1 4-5 5 5 AATCC 3-4 6-7 3 5 4 4

Standard

Ironing Fastness

Alkali

Acid

ISO

3

AATCC

3-4

InChI:InChI=1/C14H8O7S.Na.H2O/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);;1H2/q;+1;/p-1

Synthetic route

C21H11BO8S(2-) → alizarin red S (130-22-3) + 3H-benzo[c][1,2]oxaborol-1-ol (5735-41-1)

Conditions	Yield
In acetonitrile Kinetics; pH-value; Inert atmosphere; Darkness; Sealed tube;

C28H12O14S2Zn(2-)*2Na(1+) + hydrogen sulfide (7783-06-4) → alizarin red S (130-22-3) + zinc sulfide

Conditions	Yield
In methanol; aq. phosphate buffer at 20℃; pH=7.4; pH-value;

potassium tetrachloropalladate(II) (10025-98-6) + alizarin red S (130-22-3) → [C6H4(CO)2C6HO(OH)SO3Na]2Pd

Conditions	Yield
With potassium hydroxide In water mixed, treated with equimolar amount of KOH, heated at 100°C for1 h, standed for 12 h, pptd.(ethanol); filtered, dried (air), elem. anal., IR;	90%

alizarin red S (130-22-3) + nickel dichloride → Ni(C6H4(CO)2C6H(OH)(O)SO3)2(2-)*2Na(1+)=Ni(C6H4(CO)2C6H(OH)(O)SO3Na)2

Conditions	Yield
In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	82%

alizarin red S (130-22-3) + copper dichloride → [Cu(C6H4(CO)2C6H(O)2SO3)(H2O)](1-)*Na(1+)*H2O=[Cu(C6H4(CO)2C6H(O)2SO3Na)(H2O)]*H2O

Conditions	Yield
With water In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	81%

alizarin red S (130-22-3) + nickel dichloride → [Ni(C6H4(CO)2C6H(O)2SO3)(H2O)](1-)*Na(1+)=[Ni(C6H4(CO)2C6H(O)2SO3Na)(H2O)] (90568-30-2)

Conditions	Yield
With water In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	79%

alizarin red S (130-22-3) + cobalt(II) chloride (7646-79-9) → [Co(C6H4(CO)2C6H(O)2SO3)(H2O)](1-)*Na(1+)=[Co(C6H4(CO)2C6H(O)2SO3Na)(H2O)] (90568-29-9)

Conditions	Yield
With water In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	78%

alizarin red S (130-22-3) + ferric nitrate (7782-61-8) → Fe(C6H4(CO)2C6H(O)2SO3)2(3-)*H(1+)*2Na(1+)=Fe(C6H4(CO)2C6H(O)2SO3Na)(C6H4(CO)2C6H(OH)(O)SO3Na)

Conditions	Yield
In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	77%

alizarin red S (130-22-3) + copper(II) sulfate (7758-99-8) → [Cu2(C6H4(CO)2C6H(O)2SO3)(SO4)(H2O)4](1-)*Na(1+)=[Cu2(C6H4(CO)2C6H(O)2SO3Na)(SO4)(H2O)4] (89973-58-0)

Conditions	Yield
With water In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	77%

alizarin red S (130-22-3) + ferric nitrate (7782-61-8) → [Fe(C6H4(CO)2C6H(O)2SO3)(NO3)(H2O)2](1-)*Na(1+)=[Fe(C6H4(CO)2C6H(O)2SO3Na)(NO3)(H2O)2] (90386-78-0)

Conditions	Yield
With water In water ligand refluxed for 30 min with H2O, filtered at 100°C, added toaq. soln. of metal salt, refluxed for 2 h, left overnight at 25°C; ppt. filtered, washed with H2O and MeOH, dried at 85°C, stored over P2O5 (vac.); elem. anal.;	76%

2-Chlorobutanal (28832-55-5) + alizarin red S (130-22-3) → C18H13O8S(1-)*Na(1+)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 12h;	75.4%

alizarin red S (130-22-3) + β‐cyclodextrin (7585-39-9) → Na(1+)*C14H7O7S(1-)*C42H70O35

Conditions	Yield
In ethanol for 0.5h;	75%

3-(4-(bromomethyl)phenyl)acrylaldehyde + alizarin red S (130-22-3) → C24H15O8S(1-)*Na(1+)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 12h;	72.4%

3-bromocyclopentene (36291-48-2) + alizarin red S (130-22-3) → C19H13O7S(1-)*Na(1+)

Conditions	Yield
Stage #1: alizarin red S With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #2: 3-bromocyclopentene In N,N-dimethyl-formamide for 12.5h;	67%

alizarin red S (130-22-3) → 3,4-dihydroxy-9,10-dioxo-2-anthracenesulfonyl chloride

Conditions	Yield
With chlorosulfonic acid	66%
With chlorosulfonic acid at 90 - 100℃; for 5h;	35%

arquad 316 + alizarin red S (130-22-3) → C49H102N(1+)*C14H7O7S(1-) (1526914-98-6)

Conditions	Yield
In water at 80℃; for 1h;	49%

alizarin red S (130-22-3) → C14H7O7S(2-)*Na(1+)

Conditions	Yield
With sodium dithionite; ammonia In ethanol; water at 9.9℃; pH 9-11;

alizarin red S (130-22-3) → C14H5(2)H2O7S(2-)*Na(1+)

Conditions	Yield
With sodium dithionite; ammonia In ethyl [2]alcohol; water-d2 at 9.9℃; pH 9-11;

alizarin red S (130-22-3) + phenylboronic acid (98-80-6) → sodium; 6,11-dioxo-2-phenyl-6,11-dihydro-1,3-dioxa-2-bora-cyclopenta[a]anthracene-4-sulfonate

Conditions	Yield
Equilibrium constant;
In aq. phosphate buffer; dimethyl sulfoxide pH=7.4;

lead(II) nitrate + alizarin red S (130-22-3) → Na(1+)*{Pb(C14H5O7S)}(1-)=Na{Pb(C14H5O7S)}

Conditions	Yield
In water react. of sodium alizarinsulfonate with Pb(NO3)2 in aq. medium;; pptn.;
In water

alizarin red S (130-22-3) + copper(II) sulfate (7758-99-8) → Na(1+)*Cu(2+)*C14H5O7S(3-)=Na{CuC14H5O7S}

Conditions	Yield
In water spectrophotometric detection;;

alizarin red S (130-22-3) + cobalt(II) chloride (7646-79-9) → sodium 1,2-dihydroxyanthraquinone-3-sulphonate Co(II) complex

Conditions	Yield
In water a soln. of CoCl2 was added to a soln. of alizarine red S (both in H2O, as concd. as possible); then 0.1 N NH4OH was added drop-wise with stirring until pH 7 had been achieved;; after filtration, the ppt. was washed several times with H2O, EtOH and Et2O, dried in a vac. desiccator over P2O5; elem. anal.;;

alizarin red S (130-22-3) + nickel dichloride → sodium 1,2-dihydroxyanthraquinone-3-sulphonate Ni(II) complex

Conditions	Yield
In water a soln. of NiCl2 was added to a soln. of alizarine red S (both in H2O, as concd. as possible); then 0.1 N NH4OH was added drop-wise with stirring until pH 7 had been achieved;; after filtration, the ppt. was washed several times with H2O, EtOH and Et2O, dried in a vac. desiccator over P2O5; elem. anal.;;

alizarin red S (130-22-3) + manganese(ll) chloride → sodium 1,2-dihydroxyanthraquinone-3-sulphonate Mn(II) complex

Conditions	Yield
In water a soln. of MnCl2 was added to a soln. of alizarine red S (both in H2O, as concd. as possible); then 0.1 N NH4OH was added drop-wise with stirring until pH 7 had been achieved;; after filtration, the ppt. was washed several times with H2O, EtOH and Et2O, dried in a vac. desiccator over P2O5; elem. anal.;;

copper(ll) sulfate pentahydrate + alizarin red S (130-22-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Cu(C14H5O4SO3)(1-)*HCON(CH3)2

Conditions	Yield
In N,N-dimethyl-formamide solns. mixing;

cerium(III) sulfate + alizarin red S (130-22-3) → Ce(C14H5O4SO3)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In ethanol; water solns. mixing (pH 4-9, HCl or NaOH);
With hydrogenchloride; sodium hydroxide In water solns. mixing (pH 4-9, HCl or NaOH);
With hydrogenchloride; sodium hydroxide In water; dimethyl sulfoxide solns. mixing (pH 4-9, HCl or NaOH);
With hydrogenchloride; sodium hydroxide In water; acetone solns. mixing (pH 4-9, HCl or NaOH);

copper(ll) sulfate pentahydrate + cerium(III) sulfate + alizarin red S (130-22-3) → Cu2Ce2(C14H5O4SO3)4(2-)

Conditions	Yield
With hydrogenchloride In water; dimethyl sulfoxide solns. mixing (pH(opt) 3, HCl);
With hydrogenchloride In water solns. mixing (pH(opt) 3, HCl);
With hydrogenchloride In water; N,N-dimethyl-formamide solns. mixing (pH(opt) 3, HCl);

sodium molybdate + alizarin red S (130-22-3) → MoO3C14H5O4SO3(3-)

Conditions	Yield
With sodium nitrate In methanol in aq. soln. (ionic strength of 0.1 with NaNO3) at 25°C; detected by UV;

Upstream product

• 7783-06-4 hydrogen sulfide 

Downstream Products

• 88-99-3 benzene-1,2-dicarboxylic acid 
• 526-86-3 2,3-dimethyl-1,4-benzoquinone 
• 7446-11-9 sulfur trioxide 
• 123-73-9 crotonaldehyde 

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Relevant articles and documents

Alizarin red S-zinc(II) fluorescent ensemble for selective detection of hydrogen sulphide and assay with an H2S donor

A new Alizarin Red S based fluorescent probe ARS-Zn(ii) has been reported for the detection of H2S in aqueous buffer solution. In the presence of zinc ions, ARS displayed an increase in fluorescence intensity through the formation of an ARS-Zn(ii) ensemble. The addition of H2S to the ensemble caused the disassembly of the metal and ARS, which restored the fluorescence intensity of ARS. This sensing ensemble exhibited H2S-selectivity over other biothiols and biologically relevant analytes. The calculated detection limit of ARS-Zn(ii) with H2S was 92 nM. ARS-Zn(ii) also detected H2S in serum under physiological conditions. Moreover, as a practical application, it could be used for the real time monitoring of H2S released from the H2S-donor molecule benzoic (methyl carbonic) dithioperoxyanhydride and also applied to live cell imaging. The reported ensemble ARS-Zn(ii) has advantages like ready availability, high selectivity with good sensitivity, fast response time, higher excitation (520 nm) and emission (625 nm) wavelengths and real time fluorescence assay with H2S donors.