72-48-0 Usage
Description
1,2-Dihydroxy-9,10-anthracenedione, also known as Alizarin, is an orange-red organic compound that belongs to the anthraquinone family. It is characterized by the presence of two hydroxy groups at positions 1 and 2. Alizarin is used in various industries due to its unique properties and applications.
Uses
1. Used in Antimutagenesis:
Alizarin is used as an antimutagen, which helps in preventing genetic mutations and protecting cells from damage.
2. Used in Textile Industry:
Alizarin is widely used as a prominent red dye for textile fabrics. It is known for its excellent colorfastness properties, making it a preferred choice for dyeing wool fabrics.
3. Used in Biochemical Assays:
Alizarin red is used in biochemical assays to determine the presence of calcific deposition by cells of the osteogenic lineage through colorimetry.
4. Used in Pharmaceutical Industry:
Alizarin derivatives have been evaluated as new inhibitors of the HIV-1 reverse transcriptase associated DNA polymerase and RNase H. It has also shown to inhibit proliferation, tumor growth, and suppress tumorigenesis in human osteosarcoma and breast cancer cell lines.
5. Used in Pigment Manufacturing:
Alizarin has a major application in the manufacture of madder lake pigments, commonly known as Rose madder and Alizarin crimson.
6. Used in Medical Research:
Alizarin is involved in 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 in synovial fluid to assess basic calcium phosphate crystals.
7. Used in Colorimetric Measurements:
Alizarin is used in colorimetric measurements for the quantification of amine extraction by model food simulants from epoxy polymer.
8. Used as an Organic Pigment:
Due to its color properties, Alizarin is used as an organic pigment in various applications.
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.
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].
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.
Check Digit Verification of cas no
The CAS Registry Mumber 72-48-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 2 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 72-48:
(4*7)+(3*2)+(2*4)+(1*8)=50
50 % 10 = 0
So 72-48-0 is a valid CAS Registry Number.
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
72-48-0Relevant articles and documents
Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents
Osman, Che Puteh,Ismail, Nor Hadiani,Widyawaruyanti, Aty,Imran, Syahrul,Tumewu, Lidya,Choo, Chee Yan,Ideris, Sharinah
, p. 353 - 363 (2019/06/20)
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.
COLLAGEN MATRIX WITH LOCALLY CONTROLLED INTRAFIBRILLAR AND EXTRAFIBRILLAR MINERAL CONTENT AND METHODS OF PRODUCING
-
Page/Page column, (2014/08/19)
A mineralized collagen matrix with an intrafibrillar and/or extrafibrillar gradient of mineralization for insertion replacement is disclosed. The intrafibrillar mineralization of the collagen matrix is formed by the addition of fetuin to the simulated body fluid. The gradient of intrafibrillar mineralization may stiffen the collagen matrix and simulate a natural insertion for improved cell infiltration and regeneration.
An anthraquinone scaffold for putative, two-face bim BH3 α-helix mimic
Zhang, Zhichao,Li, Xiangqian,Song, Ting,Zhao, Yan,Feng, Yingang
, p. 10735 - 10741 (2013/02/23)
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.