Artemisinin supplier | CasNO.63968-64-9

Name
Artemisinin
EINECS 1806241-263-5
CAS No. 63968-64-9
Article Data61
CAS DataBase
Density 1.24 g/cm3
Solubility
Melting Point 156-157 oC
Formula C15H22O5
Boiling Point 389.9oC at 760 mmHg
Molecular Weight 282.337
Flash Point 172oC
Transport Information
Appearance Crystalline Solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (+)-Arteannuin;Qinghaosu;[3R-(3R,5aS,6S,8aS,9R,10R,12S,12aR**)]-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-one;
PSA 53.99000
LogP 2.39490

Synthetic route

: (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

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; magnesium oxide; Rh2(fb)4 In dichloromethane for 24h; Heating;	96%

: 85031-60-3
4α-hydroperoxy-amorph-5-en-12-oic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 104196-16-9
(3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid In toluene Flow reactor; chemoselective reaction;	A 81% B 7%

: 96-99-1
4-chloro-3-nitrobenzoate

: 7β-hydroxyartemisinin

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	75%

: 85031-60-3
4α-hydroperoxy-amorph-5-en-12-oic acid

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; copper(I) triflate at 20℃; Temperature;	65%

: 1267472-30-9
(3R)-dihydroarteannuin B acid methyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	62.2%

: 1267472-33-2
(3R)-dihydroarteannuin B acid ethyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	62%
With 5,10,15,20-tetraphenyl-21H,23H-porphine; trifluoroacetic acid In dichloromethane at -15 - -10℃; Irradiation; Industrial scale;	370 kg

: 1267472-35-4
(3R)-dihydroarteannuin B acid benzyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	59.2%

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 207446-83-1
arteanniun H

Conditions

Conditions	Yield
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation; High pressure; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane; toluene at 25℃; for 0.333333h;	A 59.1% B 6.1%
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / -20 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 0.33 h / 25 °C / 750.08 Torr / Flow reactor View Scheme
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / -20 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 0.33 h / 50 °C / 750.08 Torr / Flow reactor View Scheme
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 60 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 0.33 h / 25 °C / 750.08 Torr / Flow reactor View Scheme
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 60 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 0.33 h / 50 °C / 750.08 Torr / Flow reactor View Scheme

: 1267472-31-0
(3R)-dihydroarteannuin B acid 2,2,2-trichloroethyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	58.7%

: 1267472-37-6
(3R)-dihydroarteannuin B acid phenyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	58.4%

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 105231-07-0
(4R,4aS,7R,8S)-4,7-Dimethyl-8-(3-oxo-butyl)-4,4a,5,6,7,8-hexahydro-isochromen-3-one

Conditions

Conditions	Yield
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation; High pressure; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane; toluene at 0℃; for 1h; Solvent; Temperature; Time;	A 55.6% B 6.8%
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation; High pressure; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane; toluene at -15℃; for 0.333333h;	A 18% B 21.3%
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / -20 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 1 h / 0 °C / 750.08 Torr / Flow reactor View Scheme
Multi-step reaction with 2 steps 1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 60 °C / Flow reactor; UV-irradiation 2: trifluoroacetic acid; oxygen / toluene / 1 h / 0 °C / 750.08 Torr / Flow reactor View Scheme

: 1267472-43-4
(3R)-dihydroarteannuin B acid 2-chloroethyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	54.9%

: 1267472-39-8
(3R)-dihydroarteannuin B acid propyl carbonate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;	54.5%

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane under 8625.86 Torr; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane at 0℃; for 2h;	50%
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane under 8625.86 Torr; UV-irradiation; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane at 0℃; under 760.051 Torr; for 2h; Pressure; Temperature; Solvent;	50%
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at 0℃; under 760.051 Torr; for 0.0333333h; Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; for 2h; Time; Temperature; Concentration; UV-irradiation;	50%

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With porphyrin; trifluoroacetic acid In toluene at 25℃; Temperature; Reagent/catalyst; Irradiation;	50%

: 126189-95-5
(+)-deoxoartemisinin

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate	49%

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 104196-16-9
(3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one

C: 207446-83-1
arteanniun H

Conditions

Conditions	Yield
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation; High pressure; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane; toluene at 50℃; for 0.333333h;	A 47% B 5.5% C 7.2%

...Expand

: 85031-63-6
5α-hydroperoxy-amorph-5-en-12-oic acid methyl ester

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: (R)-2-((4R,4aS)-4,7-Dimethyl-2,3,4,4a,5,6-hexahydro-naphthalen-1-yl)-propionic acid methyl ester

C: 422565-48-8
(R)-2-[(1S,3S,4R)-2-Formyl-2-[(2R,4aS,5R,8S)-8-((R)-1-methoxycarbonyl-ethyl)-2,5-dimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-ylperoxy]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

D: (R)-2-[(1S,3S,4R)-2-Formyl-2-[(2S,3R,6S)-6-((R)-1-methoxycarbonyl-ethyl)-3-methyl-2-(3-oxo-butyl)-cyclohex-(E)-ylidenemethoxy]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Conditions

Conditions	Yield
In chloroform-d1 for 2556.75h; Further byproducts given;	A 3% B 40% C 4% D n/a

...Expand

: 85031-59-0, 110715-68-9, 126643-10-5
dihydroartemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 104196-16-9
(3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one

C: 105231-07-0
(4R,4aS,7R,8S)-4,7-Dimethyl-8-(3-oxo-butyl)-4,4a,5,6,7,8-hexahydro-isochromen-3-one

D: 207446-83-1
arteanniun H

Conditions

Conditions	Yield
Stage #1: dihydroartemisinic acid With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation; High pressure; Stage #2: With oxygen; trifluoroacetic acid In dichloromethane; toluene at 75℃; for 0.333333h;	A 31.2% B 6.1% C 9.6% D 7.5%

...Expand

: 1393603-22-9
4-((7R,8S)-3-methoxy-4,7-dimethyl-3-((triisopropylsilyl)oxy)-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)butan-2-one

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
Stage #1: 4-((7R,8S)-3-methoxy-4,7-dimethyl-3-((triisopropylsilyl)oxy)-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)butan-2-one With ammonium molibdate; dihydrogen peroxide In water; tert-butyl alcohol at 20℃; for 72h; Stage #2: With toluene-4-sulfonic acid In dichloromethane at 20℃; for 72h;	29%

: 87322-20-1
(R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
Stage #1: (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester With hydrogenchloride; oxygen; rose bengal In methanol at -78℃; for 4h; UV-irradiation; Stage #2: With perchloric acid for 28h;	10%

: 101020-89-7
dehydroqinghaosu

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 113472-97-2
(+)-9-epiartemisinin

C: 9β-hydroxydeoxy-11-epi-artemisinin

D: 9β-hydroxy-11-epi-artemisinin

Conditions

Conditions	Yield
With Aspergillus niger NRRL 599; culture medium In water; acetone at 25℃; for 240h; Hydrogenation; oxidation; deoxygenation;	A n/a B 8.9% C 5.5% D 7.1%

...Expand

: 80286-58-4
artemisinic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 50906-56-4
(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one

Conditions

Conditions	Yield
In water at 30℃; for 2h; cell-free extract from Artemisia annua L. (Asteraceae), EDTA, HEPES with DDT buffer, pH 7.15; Title compound not separated from byproducts;

: 116399-93-0
(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With ozone; trifluoroacetic acid 1.) MeOH, -78 deg C, 2.) CHCl3, H2O; Yield given. Multistep reaction;

: 116399-93-0
(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 72826-63-2
2-deoxyartemisinin

Conditions

Conditions	Yield
With oxygen; ozone; trifluoroacetic acid 1.) CH2Cl2, -78 deg C, 2.) CDCl3; Yield given. Multistep reaction. Yields of byproduct given;

: 116400-02-3
2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane

A: 63968-64-9
C12H13O2(CH3)3(O)(OO)

B: 72826-63-2
2-deoxyartemisinin

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; sulfuric acid; oxygen; silica gel; ozone 1.) CH2Cl2, -78 deg C, 2 min, 2.) CH2Cl2, 22 deg C, overnight; Yield given. Multistep reaction. Yields of byproduct given;

: Sodium; (R)-2-[(1S,3S,4R)-2-[1-methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
With formic acid; oxygen 1.) MeOH, irradiation, -78 ded C, 2.) CH2Cl2, 0 deg C, 24 h; Yield given;

: Benzoic acid (2R,4aR,5R,8R,8aS)-5-((R)-1-methoxycarbonyl-ethyl)-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 71939-50-9
dihydroartemisinin

Conditions

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 1.25h;	100%
With methanol; sodium tetrahydroborate at 0℃; for 3h; Inert atmosphere;	100%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 0.5h; Inert atmosphere; Green chemistry;	98%
With sodium tetrahydroborate In methanol at 0℃; for 1h;	91%
With sodium tetrahydroborate In methanol at 0 - 5℃; for 3h;	79%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 81496-81-3
dihydroartesiminin

Conditions

Conditions	Yield
With sodium tetrahydroborate; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at -10 - 0℃; for 5h; Solvent; Inert atmosphere; Large scale;	99.6%
With sodium tetrahydroborate In methanol at 0℃;
With diisobutylaluminium hydride at -78℃;

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 71939-50-9
dihydroartemisinin

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 0℃; for 3h;	98%
With sodium tetrahydroborate In methanol at 0 - 5℃; for 3.33333h;	97.15%
With sodium tetrahydroborate In methanol for 1.25h;	96%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 72826-63-2
2-deoxyartemisinin

Conditions

Conditions	Yield
With zinc In acetic acid for 2.5h; Ambient temperature;	98%
With hydrogen; Lindlar's catalyst In methanol for 10h;	88%
With hydrogen; Lindlar's catalyst In methanol Ambient temperature;	86%

: 108-30-5
succinic acid anhydride

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 88495-63-0
artesunate

Conditions

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%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 7β-hydroxyartemisinin

Conditions

Conditions	Yield
With sodium phosphite; phosphite dehydrogenase; P450 variant IV-H4; oxygen; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer at 20℃; for 12h; pH=8; Reagent/catalyst; Time;	92%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 9α-hydroxyartemisinin

Conditions

Conditions	Yield
With sodium phosphite; phosphite dehydrogenase; P450 variant II-H10; oxygen; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer at 20℃; for 12h; pH=8;	91%

: 67-56-1
methanol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

A: 95851-77-7
(R)-2-((1R,4S,4aR,7R,9aS)-4a-Formyl-7-hydroxy-1,7-dimethyl-octahydro-5,6-dioxa-benzocyclohepten-4-yl)-propionic acid methyl ester

B: 103740-01-8
(R)-2-[(1S,3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid for 0.166667h;	A n/a B 90%

...Expand

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 75-36-5
acetyl chloride

: 75887-51-3
dihydroartemisinin acetate

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate Stage #2: acetyl chloride With pyridine	90%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 6a-hydroxy-artemisinin

Conditions

Conditions	Yield
With sodium phosphite; phosphite dehydrogenase; P450 variant X-F11; oxygen; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer at 20℃; for 12h; pH=8; Reagent/catalyst; Time;	90%

: 101020-89-7
dehydroqinghaosu

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: C30H42O10

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Stage #2: dehydroqinghaosu In tetrahydrofuran at -78℃; for 5h; Further stages.;	88%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 185418-56-8
(1S,4R,5R,8R,9R,10R,12R,13R)-1,5,9-trimethyl-10-(trifluoromethyl)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-ol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 25h; Ambient temperature;	87%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

A: 98379-74-9
(3aS,4R,6aS,7R,10S,10aR)-10-(acetyloxy)octahydro-4,7-dimethyl-8H,10H-furo[3,2-i][2]benzopyran-8-one

B: (3R,3aS,6R,6aS,8R,9S,10aS,10bR)-octahydro-8-hydroxy-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-2(3H)-one

Conditions

Conditions	Yield
With pyridine; iron(III) chloride In acetonitrile for 36h;	A 85% B 8%
With meso-tetraphenylporphyrin iron(III) chloride; N-acetylcystein In dichloromethane for 0.75h;	A 74% B n/a
With 1H-imidazole; iron(III) trifluoromethanesulfonate; N-acetylcystein In acetonitrile for 18h;	A 41% B 50%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 1037585-91-3
9-fluoroartemisinin

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: With N-fluorobenzene sulfonamide In tetrahydrofuran at -78℃; for 1h; Further stages.;	85%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

allyl halogenide: allyl halogenide

: (3R,6R,9S,12S,12aR)-9-allyl-3,6,9-trimethyloctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #3: allyl halogenide With diethylzinc In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	82%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 405261-71-4
trimethylsilyl (1S,4R,5R,8R,9R,10R,12S,13R)-1,5,9-trimethyl-10-(trifluoromethyl)-11,14,15,16-tetraoxatetracyclo[10.3.1.0.4,1308,13]hexadec-10-yl ether

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 7h;	79%

: 71-23-8
propan-1-ol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: C18H30O5

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; amberlyst-15 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: propan-1-ol In dichloromethane at 20℃; for 72h;	79%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

A: 98379-74-9
(3aS,4R,6aS,7R,10S,10aR)-10-(acetyloxy)octahydro-4,7-dimethyl-8H,10H-furo[3,2-i][2]benzopyran-8-one

B: 3α-hydroxydeoxyartemisinin

Conditions

Conditions	Yield
With iron(II) chloride In acetonitrile for 0.0333333h; Mechanism; Ambient temperature;	A 78% B 17%
With iron(II) chloride In acetonitrile for 0.25h; Ambient temperature;	A 78% B 17%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 2-deuteriodihydroqinghaosu

Conditions

Conditions	Yield
With sodium borodeuteride In methanol for 1h; Reduction;	77%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 81290-20-2
(trifluoromethyl)trimethylsilane

: C16H23F3O5

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO); (trifluoromethyl)trimethylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; Stage #2: With water at 20℃; for 0.5h; Further stages.;	77%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 103740-01-8
(R)-2-[(1S,3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid In methanol	75%
With iron(III) chloride In diethyl ether for 1.5h;
With trifluoroacetic acid In methanol Heating;

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 10-deoxoartemisinin

Conditions

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran	75%
Multi-step reaction with 2 steps 1: 100 percent / DIBAL-H / CH2Cl2 / 1.25 h / -78 °C 2: 1.) Et3SiH, 2.) BF3*OEt2 / 1.) CH2Cl2, -78 deg C, 10 min, 2.) CH2Cl2, -78 deg C, 3 h View Scheme

: 71-41-0
pentan-1-ol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: C20H34O5

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; amberlyst-15 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: pentan-1-ol In dichloromethane at 20℃; for 56h;	74%

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 107-21-1
ethylene glycol

: C18H30O6

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 17h; Reflux;	74%

: 67-56-1
methanol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 95851-75-5
(R)-methyl 2-((3R,6R,9aR)-9a-formyl-3-methoxy-3,6-dimethyloctahydro-3H-benzo[c][1,2]dioxepin-9-yl)propanoate

Conditions

Conditions	Yield
With trifluoroacetic acid for 5h; Reflux;	73%
With sulfuric acid for 3h; Yield given;

: 110-63-4
Butane-1,4-diol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: C19H32O6

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate; amberlyst-15 In tetrahydrofuran at 20℃; for 0.5h; Stage #2: Butane-1,4-diol In dichloromethane at 20℃; for 55h;	73%

Artemisinin Chemical Properties

Molecular Structure:
Molecular Formula: C₁₅H₂₂O₅
Molecular Weight: 282.33
CAS NO: 63968-64-9
H bond acceptors: 5
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 53.99 Å²
Index of Refraction: 1.533
Molar Refractivity: 70.31 cm³
Molar Volume: 226.4 cm³
Surface Tension: 43.5 dyne/cm
Density: 1.24 g/cm³
Flash Point: 172 °C
Enthalpy of Vaporization: 63.93 kJ/mol
Boiling Point: 389.9 °C at 760 mmHg
Vapour Pressure: 2.76E-06 mmHg at 25°C
Melting point: 156-157 °C(lit.)
Alpha: 76 ^o (c=0.5,MeOH)
Appearance: Crystalline Solid
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. May absorb, and react with, carbon dioxide from the air.
Product Categories of Artemisinin (CAS NO.63968-64-9): Active Pharmaceutical Ingredients;Miscellaneous Natural Products;Others (Antibiotics for Research and Experimental Use);Antibiotics for Research and Experimental Use;Biochemistry;Standard extract;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Compounds

Artemisinin Uses

Artemisinin (CAS NO.63968-64-9) is derived from a herb used in Chinese traditional medicine, though it is usually chemically modified and combined with other medications.Combination therapies that include artemisinin are the preferred treatment for malaria and are both effective and well tolerated in patients. It is also being studied as a treatment for cancer.

Artemisinin Production

Artemisinin (CAS NO.63968-64-9) is isolated from the plant Artemisia annua. It is only produced when the plant is subjected to certain conditions, most likely biotic or abiotic stress.
Here is biosynthesis of Artemisinin .

Artemisinin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	intramuscular	> 800mg/kg (800mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
mouse	LD	unreported	> 2gm/kg (2000mg/kg)		Antimicrobial Agents and Chemotherapy. Vol. 37, Pg. 1108, 1993.
mouse	LD50	intramuscular	2800mg/kg (2800mg/kg)		Chinese Medical Journal Vol. 92, Pg. 811, 1979.
mouse	LD50	intraperitoneal	1558mg/kg (1558mg/kg)		Chinese Medical Journal Vol. 92, Pg. 811, 1979.
mouse	LD50	oral	4228mg/kg (4228mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA	Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
rat	LD50	intramuscular	2571mg/kg (2571mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA	Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
rat	LD50	oral	5576mg/kg (5576mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA	Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

Artemisinin Safety Profile

Safety Information about Artemisinin (CAS NO.63968-64-9):
Safety Statements: 22-24/25
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
WGK Germany: 2
Moderately toxic by ingestion, intramuscular, and intraperitoneal routes. When heated to decomposition it emits acrid smoke and fumes.

Artemisinin Specification

Artemisinin (CAS NO.63968-64-9) is also called (+)-Arteannuin ; Qinghaosu and [3R-(3R,5aS,6S,8aS,9R,10R,12S,12aR**)]-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-one .

Product Name

Artemisinin

Synthetic route

Artemisinin Chemical Properties

Artemisinin Uses

Artemisinin Production

Artemisinin Toxicity Data With Reference

Artemisinin Safety Profile

Artemisinin Specification

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