Alizarin

Base Information

• Chemical Name: Alizarin
• CAS No.: 72-48-0
• Deprecated CAS: 1328-02-5,84754-86-9,84754-86-9
• Molecular Formula: C14H8O4
• Molecular Weight: 240.215
• Hs Code.: 29146990
• European Community (EC) Number: 200-782-5
• NSC Number: 7212
• UNII: 60MEW57T9G
• DSSTox Substance ID: DTXSID5045960
• Nikkaji Number: J2.816I
• Wikipedia: Alizarin
• Wikidata: Q267813
• NCI Thesaurus Code: C80142
• Pharos Ligand ID: JMVW1SJL6STG
• Metabolomics Workbench ID: 50680
• ChEMBL ID: CHEMBL55814
• Mol file: 72-48-0.mol

Synonyms:1,2-dihydroxyanthraquinone;alizarin;alizarin red;alizarine

Chemical Property of Alizarin

Chemical Property:

• Appearance/Colour: orange-red crystals or powder
• Vapor Pressure: 5.34E-08mmHg at 25°C
• Melting Point: 287 °C
• Refractive Index: 1.732
• Boiling Point: 430 °C at 760 mmHg
• PKA: 6.77(at 25℃)
• Flash Point: 228 °C
• PSA: 74.60000
• Density: 1.54 g/cm³
• LogP: 1.87320
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Solubility Virtually insoluble in water; moderately soluble in e
• Water Solubility.: Soluble in hexane and chloroform. Slightly soluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 240.04225873
• Heavy Atom Count: 18
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

Alizarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Anthraquinone Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
• Recent ClinicalTrials: Effects of Azithromycin as an Adjunct to Scaling and Root Planning in the Treatment of Periodontitis
• Uses: antimutagen 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. 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.

Technology Process of Alizarin

There total 137 articles about Alizarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + Phthaloyl dichloride (88-95-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0,84754-86-9)

Guidance literature:

With aluminium trichloride; In nitrobenzene; at 80 ℃; for 0.25h;

Reference yield: 55.0%

phthalic anhydride (85-44-9) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 1,2-dihydroxy-9,10-anthracenedione (72-48-0,84754-86-9)

Guidance literature:

With aluminium trichloride; sodium chloride; at 165 ℃; for 4h;

DOI:10.1021/jm0492655

Reference yield: 45.0%

1-nitroanthraquinone (82-34-8) → 1-hydroxyanthraquinone (129-43-1) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0,84754-86-9)

Guidance literature:

With potassium hydroxide; Cumene hydroperoxide; In dimethyl sulfoxide; at 15 - 25 ℃; for 10h;

DOI:10.1002/prac.19923340609

upstream raw materials:

tetrachloromethane

2,3-dichloro-anthraquinone

phthalic anhydride

benzo-1,4-dioxane

Downstream raw materials:

1-hydroxy-2-methoxyanthraquinone

alizarin dimethyl ether

phenol

2-hydroxy-9,10-anthraquinone

Refernces

• 1、 Ye, Man-Yi,Yao, Gui-Yang,Pan, Ying-Ming,Liao, Zhi-Xin,Zhang, Ye,Wang, Heng-Shan. "Synthesis and antitumor activities of novel α-aminophosphonate derivatives containing an alizarin moiety". . p. 116 - 128. Retrieved 2014/07/08.
• 2、 Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu. "Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues". . p. 10042 - 10055. Retrieved 2013/09/23.