72-48-0

Basic information

• Product Name: 1,2-Dihydroxy-9,10-anthracenedione
• Synonyms: 10-Anthracenedione,1,2-dihydroxy-9;9,10-Anthracenedione, 1,2-dihydroxy-;9,10-Anthracenedione,1,2-dihydroxy-;Ailzarin(c.1.No.5800);Aliazrin;Alizarin B;Alizarin,CI 58000;Alizarina
• CAS NO: 72-48-0
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.213
• EINECS: 200-782-5
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Hydroxyanthraquinones;Inhibitors;Anthraquinone;Miscellaneous
• Mol File: 72-48-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 287 °C
• Boiling Point: 430 °C
• Flash Point: 430°C subl.
• Appearance: Orange to orange-brown/Fine Powder
• Density: 1.06 g/mL at 20 °C
• Vapor Pressure: 5.34E-08mmHg at 25°C
• Refractive Index: 1.5190 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Solubility Virtually insoluble in water; moderately soluble in e
• PKA: 6.77(at 25℃)
• Water Solubility: Soluble in hexane and chloroform. Slightly soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,251
• BRN: 1914037
• CAS DataBase Reference: 1,2-Dihydroxy-9,10-anthracenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dihydroxy-9,10-anthracenedione(72-48-0)
• EPA Substance Registry System: 1,2-Dihydroxy-9,10-anthracenedione(72-48-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36-24/25-22
• WGK Germany: 3
• RTECS: YO8300000
• TSCA: Yes
• Hazardous Substances Data: 72-48-0(Hazardous Substances Data)

Usage

History

In ancient times, alizarin was the preferred red dye. Cloth dyed with it has been found in Egyptian tombs dating 6000 years ago. The dye is found in the madder plant, a member of the Rubiaceae family. In 1944 about 35 species of this plant were known, but the use of more sophisticated analytical methods led to the detection of many more species; by 1984 the number had increased to 50. Alizarin is a mordant dye forming various colored coordination complexes with different metallic salts.

Uses

Different sources of media describe the Uses of 72-48-0 differently. You can refer to the following data:
1. antimutagen
2. Alizarin is used widely as a prominent red dye for textile facbrics. Alizarin red is now used in biochemical assay to determine quantitatively by colorimetry, the presence of calcific deposition by ce lls of the osteogenic lineage. Alzarine derivatives was evaluated as new inhibitors of the HIV-1 reverse transcriptase associated DNA polymerase and RNase H. Alizarin was also shown to inhibit prolife ration, tumor growth and suppress tumorigenesis in human osteosarcoma and breast cancer cell representative for bone metastasis.
3. Alizarin has a major application in the manufacture of the madder lake pigments which is commonly called as Rose madder and Alizarin crimson. It is involved in the studies of bone growth, osteoporosis, bone marrow and calcium deposits in the vascular system. It is also used as a stain in calcite and aragonite to identify calcium carbonate, and synovial fluid to asses for basic calcium phosphate crystals. It is used in colorimetric measurements for quantification of amine extraction by model food simulants from epoxy polymer.

Definition

Different sources of media describe the Definition of 72-48-0 differently. You can refer to the following data:
1. ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione in which the two hydroxy groups are located at positions 1 and 2.
2. An important orange-red organic compound used in the dyestuffs industry to produce red lakes. It occurs naturally in the root of the plant madder and may also be synthesized from anthraquinone.
3. alizarin: An orange-red compound,C14H8O4. The compound is a derivativeof anthraquinone, with hydroxylgroups substituted at the 1and 2 positions. It is an importantdyestuff producing red or violetlakes with metal hydroxide.Alizarin occurs naturally as the glucosidein madder. It can be synthesizedby heating anthraquinone withsodium hydroxide.

Preparation

(a) 2 – Bromoanthraquinone and Potassium hydroxide heating; (b) 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid (Sodium) and Sodium hydroxide and Sodium nitrate and Sodium chlorate heating; (C) Anthracene-9,10-dione?and Sodium hydroxide and Sodium chlorate and Sodium nitrate heating (GP 186526); (d) in the presence of Sodium nitrite and Sodium hydroxide and Anthracene-9,10-dione?and Sodium nitrate heating (GP 241806245 987); (e) in the Oxidant and Sodium sulfite and the presence of lime, anthracene in a nitrocellulose derivatives and Sodium hydroxide heating (GP 292247); (f) 2 – Anthraquinonesulfonic acid in the presence of air, with the Sodium hydroxide Etanol wetting treatment (GP 287270); (g) 2-Chloroanthracene-9,10-dione Sodium chlorate in the presence of alkali fusion for (USP 1744815); (h) 2-Methylanthracene-9,10-dione in the presence of Oxidant, with Sodium hydroxide treatment (BP 293328).

Biological Activity

alizarin is an anthraquinone dye for detecting the presence of calcium salts [1].alizarin belongs to the anthraquinone group. it is a chelator for calcium and is commonly used to stain the calcifying or calcio-receptive zone of the collagenous matrix where calcium salts are being deposited. on the other hand, the alizarin complexone is used for bone staining in vivo to study bone remodeling [1].alizarin is proved to have anti-tumor efficacy. it suppresses the cell growth of the prostate cancer, breast cancer and osteosarcoma cell lines in vitro. among these, the osteosarcoma cells appear to be most sensitive. the ic50 values of alizarin against three osteosarcoma cell lines saos-2, mg-63 and u-2 os are 27.5, 29 and 69.9μg/ml, respectively. alizarin inhibits the cell growth through cell proliferation blockade rather than induction of apoptosis. it inhibits the phosphorylation of erk. in addition, alizarin is also found to induce s-phase arrest as well as a decrease of the g0/g1 and g2/m phases [1].

Properties and Applications

commonly known as 1,2-Dihydroxyanthracene-9,10-dione , calcium, aluminum mordanting for red to blue light red, chromium for dark blue light red, iron as dark purplish red. Claybank powder. Slightly soluble in water, but soluble in Methanol, Acetone Etanol, boiling, alkali and Cellosolve, slightly soluble in benzene, Carbon tetrachloride, insoluble in cold Etanol, Stout solvent, soluble in alkali liquor for royal purple. In concentrated sulfuric acid for yellow red, red yellow after diluted produce precipitation; In the Sodium hydroxide to purple. Used for wool fabric dyeing and used as organic pigment. Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water Alkali Acid ISO 3-4 7 3-4 1 3 4 4 AATCC Dry 2,wet 5 7 2-3 4 4 5

Standard

Ironing Fastness

Alkali

Acid

ISO

3-4

Purification Methods

Alizarin crystallises from glacial acetic acid or 95% EtOH. It can also be sublimed at 110o/2mm. It is an indicator with max at 452nm (pH 5.8) and 520nm (pH 7.2). [Beilstein 8 IV 3256.]

references

[1] fotia c, avnet s, granchi d, baldini n. the natural compound alizarin as an osteotropic drug for the treatment of bone tumors. j orthop res. 2012 sep;30(9):1486-92.

InChI:InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H

Synthetic route

benzene-1,2-diol (120-80-9) + Phthaloyl dichloride (88-95-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 80℃; for 0.25h;	60%
With aluminium trichloride; C6H4NO2 at 165℃; for 4h; Fridel-Crafts acylation;

phthalic anhydride (85-44-9) + benzene-1,2-diol (120-80-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With aluminium trichloride; sodium chloride at 165℃; for 4h; Fridel-Crafts acylation;	55%
Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel Crafts Acylation; Stage #2: With hydrogenchloride In water at 0 - 100℃; for 0.75h; Heating / reflux;	55%
Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel-Crafts Acylation; Stage #2: With hydrogenchloride In water at 20 - 100℃; for 0.75h;	36%

1-nitroanthraquinone (82-34-8) → 1-hydroxyanthraquinone (129-43-1) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide; Cumene hydroperoxide In dimethyl sulfoxide at 15 - 25℃; for 10h;	A 55% B 13% C 32%
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 3h;	A 45% B 8% C 35%

2-aminoanthraquinone (117-79-3) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 6,15-dihydroanthrazine-5,9,14,18-tetrone (81-77-6) + 16-hydroxy-8,17-dihydrodinaphtho<2,3-a:2',3'-i>phenazine-5,10,15,18-tetrone (16135-99-2)

Conditions	Yield
With potassium hydroxide; potassium chlorate In various solvent(s) at 168 - 172℃; for 2h;	A n/a B 48% C n/a
With potassium hydroxide; potassium chlorate In 2-ethoxy-ethanol at 168 - 172℃; for 2h; Product distribution; further solvents and oxidants;

tetrachloromethane (56-23-5) + 2,3-dichloro-anthraquinone (84-45-7) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
beim Schmelzen;

phthalic anhydride (85-44-9) + benzo-1,4-dioxane (493-09-4) → hystazarin (483-35-2) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With aluminium trichloride; sodium chloride at 130 - 140℃;
With aluminium trichloride; sodium chloride at 170 - 180℃;

phthalic anhydride (85-44-9) + benzo-1,4-dioxane (493-09-4) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With aluminium trichloride; sodium chloride at 130 - 140℃;
With aluminium trichloride; sodium chloride at 170 - 180℃;

phthalic anhydride (85-44-9) + 2-monochlorophenol (95-57-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sulfuric acid; boric acid at 240 - 255℃;

phthalic anhydride (85-44-9) + benzene-1,2-diol (120-80-9) → hystazarin (483-35-2) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With Japanese acid earth
With sulfuric acid at 180 - 200℃;
With aluminium trichloride; sulfuric acid; sodium chloride 1.) reflux, 2 h, 2.) reflux, 3 h; Multistep reaction. Title compound not separated from byproducts;

phthalic anhydride (85-44-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

2-(3,4-dimethoxybenzoyl)benzoic acid (51439-85-1) → hystazarin (483-35-2) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sulfuric acid at 100℃; Verseifen den Hystazarindimethylaether mit konz.Schwefelsaeure auf 200-205grad;

3,4-dimethoxyphthalic anhydride (1567-56-2) + benzene (71-43-2) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With aluminium trichloride Erwaermen des Reaktionsprodukts mit konz.Schwefelsaeure auf 100grad,und nachfolgend verseifen mit Jodwasserstoffsaeure;

ethanol (64-17-5) + 1,2-dihydroxy-3-hydroxyazo-anthraquinone → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

1-methyl-4-nitrosobenzene (623-11-0) + 2-hydroxy-2,4a-dihydro-anthraquinone → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
at 215℃; und Leiten von Luft durch die Reaktionsloesung;

2-hydroxy-9,10-anthraquinone (605-32-3) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium carbonate durch Schmelzen;
Multi-step reaction with 2 steps 1: aqueous ammonia / 150 °C 2: NaNO2; concentrated sulfuric acid / 190 °C View Scheme

1-nitroanthraquinone (82-34-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium carbonate durch Schmelzen;

1-hydroxyanthraquinone (129-43-1) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium carbonate durch Schmelzen;

9-nitroanthrone (6313-44-6) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sodium hydroxide; methyllithium; nitric acid; calcium carbonate at 200℃; Reagens 4: Na2SO3;

2-chloro-1-hydroxy-anthraquinone (35582-88-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
bei der Kalischmelze;

2-chloroanthracene-9,10-dione (131-09-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sodium chlorate; sodium hydroxide technische Darstellung durch Schmelzen;

2-bromoanthracene-9,10-dione (572-83-8) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-bromoanthracene-9,10-dione (572-83-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide
With sodium hydroxide

1,3-dichloroanthraquinone (602-73-3) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide bei Schmelzen;
With sodium hydroxide bei Schmelzen;
in der Kalischmelze;

anthragallol (602-64-2) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sodium amalgam

2-phenylaminoanthraquinone (36339-31-8) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1-Hydroxy-2-phenylaminoanthraquinone (68637-85-4)

Conditions	Yield
With potassium hydroxide; potassium acetate; potassium nitrate weiteres Reagens: H2O;

2,3-dichloro-anthraquinone (84-45-7) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With sodium hydroxide
durch Kalischmelze;
With potassium hydroxide

2-sulfo-anthraquinone (84-48-0) → 2-hydroxy-9,10-anthraquinone (605-32-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With potassium hydroxide

2-sulfo-anthraquinone (84-48-0) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

Conditions	Yield
With alkali anschliessendes Oxydation des gebildeten 2-Oxy-anthrachinons mit Luft;
With potassium chlorate anschliessendes Oxydation des gebildeten 2-Oxy-anthrachinons mit Luft;

Alizarin S (83-61-4) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0)

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + propynoic acid ethyl ester (623-47-2) → ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-2-acetate (1312024-63-7)

Conditions	Yield
With triphenylphosphine In toluene for 24h; Reflux;	97%

Cyclohexyl isocyanide (931-53-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(cyclohexylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	97%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 2-(2,4,4-trimethylpentan-2-ylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	96%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + benzoyl chloride (98-88-4) → 1,2-dibenzoyloxy-9,10-anthraquinone (6375-18-4)

Conditions	Yield
for 0.5h; Heating;	95%
With pyridine
at 190℃;

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + dimethyl acetylenedicarboxylate (762-42-5) → methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate (1312024-60-4)

Conditions	Yield
With triphenylphosphine In toluene for 24h; Reflux;	95%

Cyclohexyl isocyanide (931-53-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 2-(cyclohexylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	95%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(2,4,4-trimethylpentan-2-ylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	95%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → ethyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylate (1312024-61-5)

Conditions	Yield
With triphenylphosphine In toluene for 24h; Reflux;	94%

potassium tetrachloropalladate(II) (10025-98-6) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → [C6H4(CO)2C6H2O(OH)]2Pd (757898-87-6, 74091-57-9)

Conditions	Yield
With potassium hydroxide In water alizarin dissolved in boiling water with equimolar amount of KOH, K2PdCl4 added, pptd., suspn. standed overnight, cooled; ppt. filtered, washed (dilute HCl soln., water, acetone, ether), dried (air) elem. anal.;	93%
In N,N-dimethyl-formamide byproducts: KCl; mixed, suspn. stirred at 90°C, cooled, KCl filtered off; solv. removed (vac.), washed (ether), elem. anal., IR;	83%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1-Bromooctadecane (112-89-0) → 1,2-bis[octadecyloxy]anthraquinone (912278-50-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide; water	93%
Stage #1: 1,2-dihydroxy-9,10-anthracenedione With potassium carbonate In ISOPROPYLAMIDE at 80℃; for 1h; Stage #2: 1-Bromooctadecane In ISOPROPYLAMIDE for 7h;	93%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + ethyl chloromethyl ether (3188-13-4) → 2-(ethoxymethoxy)-1-hydroxyanthracene-9,10-dione

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;	93%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide (77377-52-7) → 1,2-bis(tert-butyldimethylsiloxy)-9,10-anthracenedione

Conditions	Yield
With tert-butyldimethylsilyl chloride In acetonitrile at 70℃; for 0.25h; silylation;	92%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 10-[(2,4-dinitro-phenyl)-hydrazono]-1,2-dihydroxy-10H-anthracen-9-one

Conditions	Yield
With sulfuric acid In methanol for 48h; Heating;	92%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 10-[(2,4-dinitrophenyl)hydrazono]-1,2-dihydroxy-10H-anthracen-9-one

Conditions	Yield
With sulfuric acid In ethanol at 60℃; for 2h; Product distribution / selectivity;	92%
With sulfuric acid In methanol at 50℃; for 48h; Product distribution / selectivity; Heating / reflux;	92%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + methyl iodide (74-88-4) → 1-hydroxy-2-methoxyanthraquinone (6003-11-8)

Conditions	Yield
With lithium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;	90%
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 24h;	28%
With potassium carbonate
With water; barium(II) oxide In N,N-dimethyl-formamide
With sodium hydroxide In N,N-dimethyl-formamide

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 5-methyl-o-tolyl isocyanide (71119-75-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(2,6-dimethylphenylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	90%

tetrahydrofuran (109-99-9) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → C36H28O10Si

Conditions	Yield
With tetrachlorosilane at 75℃; for 20h; Inert atmosphere; Schlenk technique;	90%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 5-methyl-o-tolyl isocyanide (71119-75-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 2-(2,6-dimethylphenylamino)-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho[2,3-g]chromene-3,4-dicarboxylate

Conditions	Yield
In toluene for 24h; Reflux;	88%

dichloro(2-anilinopyridyl-kappa.N,C)gold (198711-19-2) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → [Au(alizarin)(2-anilinopyridyl)]

Conditions	Yield
With trimethylamine In methanol for 0.333333h; Reflux;	87%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + di(n-butyl)tin oxide (818-08-6) → [(Bu2Sn)3O(1,2-dihydroxyanthraquinone(-2H))2]

Conditions	Yield
In methanol refluxing alizarin and Bu2SnO in MeOH for 3 h; elem. anal.;	86%

cisplatin (15663-27-1) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → C14H12N2O4Pt

Conditions	Yield
Stage #1: cisplatin With silver nitrate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Stage #2: 1,2-dihydroxy-9,10-anthracenedione With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;	85%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1-dodecylbromide (143-15-7) → 1,2-bis(dodecycloxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating;	84%
With potassium carbonate In dimethyl sulfoxide; butanone for 15h; Reflux;	42%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + di(n-butyl)tin oxide (818-08-6) + dimethyl sulfoxide (67-68-5) → [Bu2Sn(1,2-dihydroxyanthraquinone(-2H))(dmso)]2 (1202356-51-1)

Conditions	Yield
In chloroform; dimethyl sulfoxide refluxing alizarin and Bu2SnO in DMSO/CHCl3 for 6 h; slow evapn. of CHCl3; elem. anal.;	83%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + bromoacetic acid (79-08-3) → 1-hydroxyanthracene-9,10-dione-2-yl 2-bromoacetate (1610041-41-2)

Conditions	Yield
Stage #1: bromoacetic acid With dmap In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dimethyl sulfoxide for 0.166667h; Stage #3: 1,2-dihydroxy-9,10-anthracenedione In dimethyl sulfoxide for 4h;	82%

trifluoromethylsulfonic anhydride (358-23-6) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → 1,2-bis[(trifluoromethylsulfonyl)oxy]anthraquinone (1234556-16-1)

Conditions	Yield
Stage #1: 1,2-dihydroxy-9,10-anthracenedione With pyridine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere;	81%
With pyridine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere;	81%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 2-Bromopropionic acid (598-72-1) → 1-hydroxyanthracene-9,10-dione-2-yl 2-bromopropionate (1610041-42-3)

Conditions	Yield
Stage #1: 2-Bromopropionic acid With dmap In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dimethyl sulfoxide for 0.166667h; Stage #3: 1,2-dihydroxy-9,10-anthracenedione In dimethyl sulfoxide for 4h;	80%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + tributylphosphine (998-40-3) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → Ru(CO)(dppe)(PBu3)(AL-2H)

Conditions	Yield
In toluene soln. of Ru-complex, dppe, and ligand in toluene was heated at reflux under Ar for 4 h, PBu3 was added, refluxed for 6 h; evapd. to dryness, recrystd. from CH2Cl2/MeOH; elem. anal.;	79%

1,2-dihydroxy-9,10-anthracenedione (72-48-0) + 1-bromoacetone (598-31-2) → 1-hydroxy-2-acetonyloxyanthraquinone (1204905-36-1)

Conditions	Yield
With potassium carbonate In acetone Reflux;	79%

(CH3CO2CH2CH2)2SnCl2 (10175-01-6) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → (CH3OCOCH2CH2)2Sn(C14H6O4) (114048-37-2)

Conditions	Yield
With ammonia In methanol byproducts: NH4Cl; heated on a water bath, ammonia soln. was added; filtered, refluxed for 1 h, recrystd. from chloroform/methanol; elem. anal.;	78%

1-methyl-piperazine (109-01-3) + formaldehyd (50-00-0) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) → C20H20N2O4

Conditions	Yield
Stage #1: 1-methyl-piperazine; formaldehyd With hydrogenchloride In ethanol at 80℃; for 2h; Stage #2: 1,2-dihydroxy-9,10-anthracenedione In ethanol at 80℃; for 10.5h; Inert atmosphere;	78%

Upstream product

• 1567-56-2 3,4-dimethoxyphthalic anhydride 
• 71-43-2 benzene 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 602-64-2 anthragallol 
• 84-48-0 2-sulfo-anthraquinone 
• 83-61-4 Alizarin S 
• 33685-60-8 9,10-dinitroanthracene 
• 568-99-0 2-amino-1-hydroxy-anthraquinone 
• 131-08-8 sodium anthraquinone-2-sulfonate 
• 1629-51-2 diacetylalizarin 
• 117-79-3 2-aminoanthraquinone 
• 483-35-2 hystazarin 
• 7664-93-9 sulfuric acid 
• 22506-55-4 2,3-dimethoxy-anthraquinone 

Downstream Products

• 6003-11-8 1-hydroxy-2-methoxyanthraquinone 
• 6003-12-9 alizarin dimethyl ether 
• 108-95-2 phenol 
• 605-32-3 2-hydroxy-9,10-anthraquinone 
• 81-54-9 1,2,4-trihydroxy-9,10-anthraquinone 
• 81-61-8 1,2,5,8-tetrahydroxy-anthraquinone 
• 120-12-7 anthracene 
• 568-93-4 3-nitroalizarin 
• 2243-71-2 4-nitroalizarin 
• 61169-36-6 1,2,4,5,6,8-hexahydroxy-9,10-anthraquinone 
• 83-61-4 Alizarin S 
• 96652-08-3 3,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid 
• 577-95-7 1,2-dihydroxyanthracene 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents

Background: A phytochemical study on medicinal plants used for the treatment of fever and malaria in Africa yielded metabolites with potential antiplasmodial activity, many of which are Anthraquinones (AQ). AQs have similar sub-structure as naphthoquinones and xanthones, which were previously reported as novel antiplasmodial agents. Objective: The present study aimed to investigate the structural requirements of 9,10-anthraquinones with hydroxy, methoxy and methyl substituents to exert strong antiplasmodial activity and to investigate their possible mode of action. Methods: Thirty-one AQs were synthesized through Friedel-Crafts reaction and assayed for antiplasmodial activity in vitro against Plasmodium falciparum (3D7). The selected compounds were tested for toxicity and probed for their mode of action against β-hematin dimerization through HRP2 and lipid catalyses. The most active compounds were subjected to a docking study using AutoDock 4.2. Results: The active AQs have similar common structural characteristics. However, it is difficult to establish a structure-activity relationship as certain compounds are active despite the absence of the structural features exhibited by other active AQs. They have either ortho- or meta-arranged substituents and one free hydroxyl and/or carbonyl groups. When C-6 is substituted with a methyl group, the activity of AQs generally increased. 1,3-DihydroxyAQ (15) showed good antiplasmodial activity with an IC50 value of 1.08 μM, and when C-6 was substituted with a methyl group, 1,3-dihydroxy-6-methylAQ (24) showed stronger antiplasmodial activity with an IC50 value of 0.02μM, with better selectivity index. Compounds 15 and 24 showed strong HRP2 activity and mild toxicity against hepatocyte cells. Molecular docking studies showed that the hydroxyl groups at the ortho (23) and meta (24) positions are able to form hydrogen bonds with heme, of 3.49 A and 3.02 A, respectively. Conclusion: The activity of 1,3-dihydroxy-6-methylAQ (24) could be due to their inhibition against the free heme dimerization by inhibiting the HRP2 protein. It was further observed that the anthraquinone moiety of compound 24 bind in parallel to the heme ring through hydrophobic interactions, thus preventing crystallization of heme into hemozoin.

Synthesis and antitumor activities of novel α-aminophosphonate derivatives containing an alizarin moiety

A series of novel α-aminophosphonate derivatives containing an alizarin moiety (6-7) was designed and synthesized as antitumor agents. MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) assay results indicated that most compounds exhibited moderate to high inhibitory activity against KB, NCI-H460, HepG 2, A549, MGC-803, Hct-116, CNE and Hela tumor cell lines. The action mechanism of representative compounds 7h, 7j and 7n were investigated by fluorescence staining assays, flow cytometric analysis and real-time polymerase chain reaction (PCR) assays, which indicated that these compounds induced apoptosis and involved G1 phase arrest by increasing the production of intracellular Ca2+ and reactive oxygen species (ROS) and affecting associated enzymes and genes. The results demonstrated that these compounds may induce apoptosis through a mitochondrion-dependent pathway.

An anthraquinone scaffold for putative, two-face bim BH3 α-helix mimic

Bim BH3 peptide features an α-helix with hotspot residues on multiple faces. Compound 5 (6-bromo-2,3-dihydroxyanthracene-9,10-dione), which adopts a rigid-plan amphipathic conformation, was designed and evaluated as a scaffold to mimic two faces of Bim α-helix. It reproduced the functionalities of both D67 and I65 on two opposing helical sides. Moreover, it maintained the two-faced binding mode during further evolution. A putative BH3 α-helix mimic and nanomolar Bcl-2/Mcl-1 dual inhibitor, 6, was obtained based on the structure of 5.