Astemisinin

Base Information

• Chemical Name: Astemisinin
• CAS No.: 63968-64-9
• Molecular Formula: C15H22O5
• Molecular Weight: 282.337
• Hs Code.: 29322985
• European Community (EC) Number: 700-290-5,613-408-4
• Wikipedia: Artemisinin
• Pharos Ligand ID: VM1YPKYFRX7U
• ChEMBL ID: CHEMBL567597
• Mol file: 63968-64-9.mol

Synonyms:Artemisinine;Qing Hau Sau;63968-64-9;Arteannuin;Astemisinin;GNF-Pf-5341;Artemisinin,(S);NSC-369397;Artemisinin, 18;SCHEMBL60303;CHEMBL567597;BDBM36349;BLUAFEHZUWYNDE-DKGJTOOQSA-N;CID452191;AKOS015894973

Chemical Property of Astemisinin

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 156-157 oC
• Refractive Index: 75 ° (C=0.5, MeOH)
• Boiling Point: 389.9oC at 760 mmHg
• Flash Point: 172oC
• PSA: 53.99000
• Density: 1.24 g/cm3
• LogP: 2.39490
• Storage Temp.: Store at +4°C
• Solubility.: Soluble to 100mM in DMSO and to 75mM in ethanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 282.14672380
• Heavy Atom Count: 20
• Complexity: 452

Purity/Quality:

98% ^*data from raw suppliers

Artemisinin ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@@](O3)(OO4)C)C
• Indications: A sesquiterpene peroxide derived from A. annua, chiefly used in the form of artemether, the methyl ester synthesized from dihydroartemisinin, or artesunate, the water-soluble hemisuccinate. Formulated for administration by the oral, intramuscular or intrarectal routes; artesunate can also be given intravenously. Artemisinin and its derivatives are valuable drugs for the management of malaria. They should not be used unnecessarily or with incomplete dosage regimens. They are indicated only in areas where multidrug resistant P. falciparum malaria is prevalent [5]. Clinically, artemisinin is mainly used to treat malaria symptoms, malignant cerebral malaria, uncomplicated malaria, and severe malaria. Combined with different antimalarial can delay and prevent resistance of malaria parasites. In additional, artemisinin can also be used for systemic lupus erythematosus or discoid lupus erythematosus. Currently, artemisinin derivatives and their compound preparations are widely used in clinic.
• Uses: Artemisia annua is used as antimalarial drugs. Clinical application has shown that artemisinin and its derivatives have special effects on treating the malaria and falciparum malaria, especially artemisinin which has stronger killing effect on Plasmodium falciparum intracellular phorozoon than other artemisinin drugs, characterized by high efficiency, rapid efficacy, low toxicity and no cross-resistance with chloroquine, etc. It can be not only used for treatment, but also for emergency treatment. It is applicable to a variety of malaria such as falciparum malaria, vivax malaria, anti-chloroquine malaria and cerebral malaria, including dangerous type. The most notable drug is dihydroartemisinin and its tablets. This drug has its antimalarial effect be 10 times as strong as artemisinin with the recurrence rate of only 1.95%, thus having been rated as China's top ten scientific and technological achievements in 1992. Artemisinin and its derivatives not only are excellent antimalarial drugs, but also have potentially attractive prospect in the treatment of other diseases. Animal experiments have found that artemisinin treatment of Clonorchis sinensis can achieve a rate of pest control being up to 100%; treatment of animal schistosomiasis can achieve a pest control rate of 33.8-99.3%. Application of artemisinin treatment of discoid lupus erythematosus can achieve a total effective rate of 90%. Its efficacy in the treatment of dengue fever is significantly better than morphine biguanide and other western medicines. Immunologists have also found that artemisinin can significantly improve the lymphocyte transformation rate and enhance the immune function of antibodies. People haven’t found toxic effect of this product on the heart, liver and kidney. People haven’t observed any significant side effects in clinical practice. An antimalarial agent that inhibits VEGF expression and NOS2. Artemisinin inhibits angiogenesis by down-regulating HIF-1α and VEGF expression in mouse embryonic stem cells. Artemisinin crosses the blood-brain barrier and is an inhibitor of human NOS2 (iNOS).
• Production method: It can be extracted from the leaves of Artemisia annua L. (Compositae). In addition to artemisinin, China also produces both artemether and sodium artemisinin.
• Description: Artemisinin is an antimalarial agent with anticancer activity. It is an iron(II) oxide-reactive endoperoxide that generates reactive oxygen species (ROS) upon cleavage of its endoperoxide bridge. It reduces the growth of various P. falciparum strains in vitro (IC50s = 3.98-20.36 nM) and reduces parasitemia in mice infected with P. falciparum with a curative dose (CD50) value of 140 mg/kg. It also reduces P. berghei infection in mice (ED50 = 5.6 mg/kg per day). Artemisinin (100-400 μM) induces cell cycle arrest in the G0/G1 phase and apoptosis and inhibits growth of SK-N-AS, BE(2)-C, SK-N-DZ, and SHEP1 neuroblastoma cells in a time- and concentration-dependent manner. It also suppresses BE(2)-C cell colony formation in a soft agar assay and reduces tumor growth in a BE(2)-C mouse xenograft model. Formulations containing artemisinin have been used in combination therapies for the treatment of malaria. Artemisinin, a sesquiterpene isolated from a traditional Chinese remedy (quinghao), is useful in the treatment of Fafciparum malaria, including infections caused by chloroquine resistant strains. It is reported to clear parasitemia quicker than i.v. quinine, and is effective in cerebral malaria.
• Physical properties: Appearance: colorless needles or white crystalline powder. Solubility: practically insoluble in water, very soluble in dichloromethane, freely soluble in acetone and ethyl acetate, and soluble in glacial acetic acid, methanol, and ethanol. Melting point: 150–153?°C. Specific optical rotation: +75 to +78°.
• Clinical Use: Malaria (including cerebral malaria), in combination with other antimalarials.

Technology Process of Astemisinin

There total 167 articles about Astemisinin 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: 96.0%

(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl carbamate → C12H13O2(CH3)3(O)(OO) (63968-64-9)

Guidance literature:

With [bis(acetoxy)iodo]benzene; magnesium oxide; Rh₂(fb)4; In dichloromethane; for 24h; Heating;

DOI:10.1021/ol071269r

Reference yield: 75.0%

4-chloro-3-nitrobenzoate (96-99-1) + 9β-hydroxyartemisinin → C12H13O2(CH3)3(O)(OO) (63968-64-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

Reference yield: 65.0%

4α-hydroperoxy-amorph-5-en-12-oic acid (85031-60-3) → C12H13O2(CH3)3(O)(OO) (63968-64-9)

Guidance literature:

With oxygen; copper(I) triflate; at 20 ℃; Temperature;

upstream raw materials:

dihydroartemisinic acid

methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

artemisinic acid

methyl <2'R,4a'S,5'R,8'R>-2-(2',5'-dimethyl-2'-hydroperoxy-2',3',4',4a',5',6',7',8'-octahydronaphthalen-8'-yl)propenoate

Downstream raw materials:

(+)-deoxyartemisinin

3,4-epoxy-4-methyl-2-pentanone

(R)-2-((4S,7R,7aS)-7-Methyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-propionic acid

C₁₅H₂₀O₄

Refernces

• 1、 Zhu, Chunyin,Cook, Silas P.. "A concise synthesis of (+)-artemisinin". . p. 13577 - 13579. Retrieved 2012.
• 2、 Kazemeini, Mohammad,Roxas, Alexander Perez,Tamtaji, Mohsen,Tyagi, Abhishek. "Selective Photooxygenation of Dihydroartemisinic Acid in a Reusable Microreactor with Physically Immobilized Photocatalysts". . . Retrieved 2022.
• 3、 Liu, Yungen,Xiao, Wenbo,Wong, Man-Kin,Che, Chi-Ming. "Transition-metal-catalyzed group transfer reactions for selective C-H bond functionalization of artemisinin". . p. 4107 - 4110. Retrieved 2007.
• 4、 Varela, Kaitlyn,Arman, Hadi D.,Yoshimoto, Francis K.. "Synthesis of [3,3-2H2]-Dihydroartemisinic Acid to Measure the Rate of Nonenzymatic Conversion of Dihydroartemisinic Acid to Artemisinin". . p. 66 - 78. Retrieved 2020.
• 5、 Amara, Zacharias,Bellamy, Jessica F. B.,Horvath, Raphael,Miller, Samuel J.,Beeby, Andrew,Burgard, Andreas,Rossen, Kai,Poliakoff, Martyn,George, Michael W.. "Applying green chemistry to the photochemical route to artemisinin". . p. 489 - 495. Retrieved 2015.