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88495-63-0

Basic Information
CAS No.: 88495-63-0
Name: Artesunate
Article Data: 11
Cas Database
Molecular Structure:
Molecular Structure of 88495-63-0 (Artesunate)
Formula: C19H28O8
Molecular Weight: 384.427
Synonyms: Butanedioicacid,mono(decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl)ester, [3R-(3a,5ab,6b,8ab,9a,10b,12b,12aR*)]-;Butanedioic acid,mono[(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]ester (9CI);Arinate;Armax 200;Arsumax;Artesunata;Artesunic acid;Asumax;Cosunate;Dihydroqinghasu hemsuccinate;Gsunate Forte;Plasmotrim;Plasmotrin;Qinghaozhi;Saphnate;WR 256283;Zysunate;
EINECS: 618-170-5
Density: 1.31 g/cm3
Melting Point: 132-135 °C
Boiling Point: 502.1 °C at 760 mmHg
Flash Point: 173.5 °C
Solubility: N/A
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 20/21/22
Safety: 24/25
Transport Information: N/A
PSA: 100.52000
LogP: 2.60240
Synthetic route
108-30-5

succinic acid anhydride

81496-81-3

dihydroartesiminin

88495-63-0

artesunate

Conditions
ConditionsYield
With dmap In 1,2-dichloro-ethane at 45℃; for 6h; Reagent/catalyst; Solvent; Temperature; Industrial scale;97%
108-30-5

succinic acid anhydride

63968-64-9

C12H13O2(CH3)3(O)(OO)

88495-63-0

artesunate

Conditions
ConditionsYield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; cation exchange resin In tetrahydrofuran at 20 - 35℃; for 0.666667h;
Stage #2: succinic acid anhydride With triethylamine In tetrahydrofuran at 20 - 35℃; for 1h;
96%
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; D-glucose In 1,4-dioxane at 20 - 30℃; for 2h;
Stage #2: succinic acid anhydride In 1,4-dioxane at 20 - 30℃; for 2h;
93%
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; cation exchange resin In tetrahydrofuran at 20 - 35℃; for 0.75h;
Stage #2: succinic acid anhydride With sodium hydrogencarbonate In tetrahydrofuran at 20 - 35℃; for 1.25h;
93%
110-15-6

succinic acid

C17H24Cl3NO5

88495-63-0

artesunate

Conditions
ConditionsYield
In dichloromethane for 4h;45%
71939-50-9

dihydroartemisinin

88495-63-0

artesunate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,8-diazabicyclo[5.4.0]undecane / CH2Cl2 / 2 h / 20 °C
2: 45 percent / CH2Cl2 / 4 h
View Scheme
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

88495-63-0

artesunate

artesunate succinimidyl ester

Conditions
ConditionsYield
Stage #1: artesunate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 1-hydroxy-pyrrolidine-2,5-dione In dichloromethane at 20℃; Inert atmosphere;
99%
Stage #1: artesunate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 1-hydroxy-pyrrolidine-2,5-dione at 20℃; for 10h;
99%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 30℃;
7689-03-4

camptothecin

88495-63-0

artesunate

C39H42N2O11

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃;90.9%

4-((1-(3-hydroxyethyl)piperidin-4-yl)amino)-3-nitrobenzenesulfonamide

88495-63-0

artesunate

C32H46N4O12S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;81.6%

4-((2-aminoethyl)amino)-3-nitrobenzenesulfonamide monohydrochloride

88495-63-0

artesunate

C27H38N4O11S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;75.5%
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

88495-63-0

artesunate

C41H46N2O12

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃;59.5%

8,9-dihydro-5-(3-hydroxy-4-methoxyphenyl)-1,2,3-trimethoxybenzo[7]annulen-7-one

88495-63-0

artesunate

C40H48O13

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Inert atmosphere;59.3%
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Chemistry

Molecular structure of Artesunate (CAS NO.88495-63-0) is:

Product Name: Artesunate
CAS Registry Number: 88495-63-0
Molecular Weight: 384.42082 [g/mol]
Molecular Formula: C19H28O8
XLogP3-AA: 2.5
H-Bond Donor: 1
H-Bond Acceptor: 8
Melting Point: 132-1350°C
Surface Tension: 51.4 dyne/cm
Density: 1.31 g/cm3
Flash Point: 173.5 °C
Enthalpy of Vaporization: 84.4 kJ/mol
Boiling Point: 502.1 °C at 760 mmHg
Vapour Pressure: 1.92E-11 mmHg at 25°C 
Product Categories: Active Pharmaceutical Ingredients;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals

Uses

 Artesunate (CAS NO.88495-63-0) can be used primarily as treatment for malaria; but artesunate has also been shown to be >90% efficacious at reducing egg production in Schistosoma haematobium infection.

Production

 Artesunate (CAS NO.88495-63-0) is prepared from Dihydroartemisinin (DHA) by reacting it with SUCCINIC ACID anhydride in basic medium. Pyridine as base/solvent, sodium bicarbonate in chloroform and catalyst DMAP (N,N-dimethylaminopyridine) and triethylamine in 1,2-dichloroethane have been used, with yields of up to 100%. A large scale process involves treatment of DHA in dichloromethane with a mixture of pyridine, a catalytic amount of DMAP and SUCCINIC ANHYDRIDE. The dichloromethane mixture is stirred for 6–9 h to get artesunate in quantitative yield. The product is further re-crystallized from dichloromethane.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 20/21/22

Specification

 Artesunate , its cas register number is 88495-63-0. It also can be called Artesunic acid ; 4-Oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10-yl hydrogen butanedioate ; Arsumax ; Artesunato ; Artesunatum ; Dihydroqinghasu hemsuccinate ; (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-ol, hydrogen succinate .It is a fine-white crystalline powder.