(1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

Base Information

• Chemical Name: (1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane
• CAS No.: 71963-77-4
• Molecular Formula: C16H26O5
• Molecular Weight: 298.379
• Hs Code.: 29329930
• European Community (EC) Number: 663-549-0
• Wikipedia: Artemether
• Mol file: 71963-77-4.mol

Synonyms:Artemether [INN];71963-77-4;CGP 56696;SM-224;C16-H26-O5;SCHEMBL7741790;s2264;CCG-267451;NCGC00386152-01;(1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane;EN300-19651964

Chemical Property of (1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

Chemical Property:

• Melting Point: 86-89oC
• Refractive Index: 1.518
• Boiling Point: 357.5 °C at 760 mmHg
• Flash Point: 140.5 °C
• PSA: 46.15000
• Density: 1.18 g/cm³
• LogP: 2.84080
• Storage Temp.: room temp
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 298.17802393
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

99%, ^*data from raw suppliers

Artemether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@@](O3)(OO4)C)OC)C
• Description: Artemether is an antiparasitic compound and a derivative of artemisinin . It induces mortality in adult wild-type and pfatp6-mutant P. falciparum but the efficacy is decreased in the mutants (IC50s = 8.2 and 13.5 nM, respectively). Artemether reduces parasitemia in P. falciparum-infected monkeys and P. berghei-infected mice with 50% curative dose (CD50) values of 7.1 and 55 mg/kg, respectively. It also reduces the worm burden of S. mansoni trematodes in mice when used at doses ranging from 200 to 500 mg/kg. Formulations containing artemether have been used in the treatment of malaria.
• Uses: Derivative of Artemisinin (A777500). Antimalarial, used to treat strains of malaria which are multi-drug resistant. atypical antidepressant, norepinephrine and dopamine reuptake inhibitor, and nicotinic antagonist Artemether and lumefantrine combination therapy is indicated for the treatment of acute uncomplicated malaria caused by Plasmodium falciparum, including malaria acquired in chloroquine-resistant areas. May also be used to treat uncomplicated malaria when

Technology Process of (1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

There total 18 articles about (1S,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane 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: 97.6%

Trimethyl orthoacetate (1445-45-0) + dihydroartemisinin (71939-50-9) → artemether (71963-77-4)

Guidance literature:

With perchloric acid; In ethanol; at 0 ℃; for 8h; pH=2; Reagent/catalyst; pH-value; Temperature;

Reference yield: 97.2%

trimethoxypropane (24823-81-2) + dihydroartemisinin (71939-50-9) → artemether (71963-77-4)

Guidance literature:

With sulfuric acid; In isopropyl alcohol; at 0 - 12 ℃; for 4h; pH=2; Solvent; Temperature; Reagent/catalyst; pH-value;

Reference yield: 96.6%

dihydroartemisinin (71939-50-9) + trimethyl orthoformate (149-73-5) → artemether (71963-77-4)

Guidance literature:

With methanesulfonic acid; In ethanol; at 5 - 20 ℃; for 3h; pH=5; Solvent; pH-value; Temperature; Reagent/catalyst;

upstream raw materials:

(S)-3-hydroxybutyric acid methyl ester

dihydroartemisinin

Methyl (R)-3-hydroxybutyrate

methanol

Downstream raw materials:

9α-acetoxy-10β-methoxyartemethin-I

3α-hydroxy-12β-methoxyartemethin-III

β-2-deoxy-9-epidihydroartemisinin

deoxydihydroqinghaosu

Refernces

• 1、 -. "Preparation method of beta-artemether". Paragraph 0046-0072. . Retrieved 2021/02/13.
• 2、 -. "Process for preparation of β - pedic methyl ether". Paragraph 0041-0044; 0067; 0068. . Retrieved 2017/08/25.