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| CAS No.: | 88495-63-0 |
|---|---|
| Name: | Artesunate |
| Molecular Structure: | |
|
|
|
| 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 |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 20/21/22 |
| Safety: | 24/25 |
| PSA: | 100.52000 |
| LogP: | 2.60240 |
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| Conditions | Yield |
|---|---|
| With dmap In 1,2-dichloro-ethane at 45℃; for 6h; Reagent/catalyst; Solvent; Temperature; Industrial scale; | 97% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| In dichloromethane for 4h; | 45% |
- 71939-50-9
dihydroartemisinin
- 88495-63-0
artesunate
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; | 90.9% |
- 88495-63-0
artesunate
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; | 59.5% |
- 88495-63-0
artesunate
| Conditions | Yield |
|---|---|
| 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: 
Xn
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.