9-epi-Artemisinin

Base Information

• Chemical Name: 9-epi-Artemisinin
• CAS No.: 113472-97-2
• Molecular Formula: C15H22O5
• Molecular Weight: 282.337
• UNII: 0474Z7MDH1
• DSSTox Substance ID: DTXSID70356309
• Nikkaji Number: J570.370K
• Wikidata: Q82135574
• ChEMBL ID: CHEMBL2111908
• Mol file: 113472-97-2.mol

Synonyms:9-epi-Artemisinin;11-epi-Artemisinin;113472-97-2;(+)-9-Epiartemisinin;9-Epiartemisinin;9-epi-Artemisinin [WHO-IP];0474Z7MDH1;(1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one;(3R,5aS,6R,8aS,9S,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one;3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9S,12S,12aR)-;Artemisinin Impurity B;epi-artemisinin;UNII-0474Z7MDH1;CHEMBL2111908;DTXSID70356309;CCG-36439;3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10(3H)-ONE, OCTAHYDRO-3,6,9-TRIMETHYL-, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.BETA.,12.BETA.,12AR*))-;3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R-(3alpha,5abeta,6beta,8abeta,9beta,12beta,12ar*))-

Chemical Property of 9-epi-Artemisinin

Chemical Property:

• PSA: 53.99000
• LogP: 2.39490
• Storage Temp.: -20°C Freezer
• Solubility.: Benzene (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightl
• 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:

95%+ or 98%+ ^*data from raw suppliers

9-epi-Artemisinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Uses: A chiral isomer of Artemisinin (A777500), an antimalarial. A metabolite of Artemisitene (A777550).

Technology Process of 9-epi-Artemisinin

There total 62 articles about 9-epi-Artemisinin 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: 73.65%

dihydroartemisinic anhydride → artemisinin (63968-64-9,113472-97-2,119241-68-8)

Guidance literature:

dihydroartemisinic anhydride; With oxygen; 5,15,10,20-tetraphenylporphyrin; In toluene; at 0 - 20 ℃; for 0.0766667h; under 7500.75 Torr; Photolysis; Irradiation;

With trifluoroacetic acid; In toluene; Solvent; Pressure; Temperature;

Reference yield: 56.0%

(3R)-dihydroarteannuin B acid ethyl carbonate (1267472-33-2) → artemisinin (63968-64-9,113472-97-2,119241-68-8)

Guidance literature:

(3R)-dihydroarteannuin B acid ethyl carbonate; With oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; at -10 ℃; for 0.5h;

trifluoroacetic acid; In dichloromethane; at -10 - 20 ℃; Product distribution / selectivity; Mercury lamp;

Reference yield: 50.0%

dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5) → artemisinin (63968-64-9,113472-97-2,119241-68-8)

Guidance literature:

dihydroartemisinic acid; With oxygen; 5,10,15,20-tetraphenylporphyrin; In dichloromethane;

With oxygen; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h; under 760.051 Torr;

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

2-[(1S,3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

(R)-2-((1R,2S,5R,6S)-12-Ethoxy-5,9-dimethyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-propionic acid ethyl ester

2-((1R,4S,4aR,7S,9aS)-7-Ethoxy-4a-formyl-1,7-dimethyl-octahydro-5,6-dioxa-benzocyclohepten-4-yl)-propionic acid ethyl ester