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GMP factory manufacturing Artemisia annua extract
Cas No: 63968-64-9
USD $ 280.0-291.0 / Metric Ton No Data 300 Kilogram/Month Weihai Moochun Bio-Tech Co., Ltd. Contact Supplier
Artemisinin
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Artemisia annua extract
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Artemisinin
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USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
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Cas No: 63968-64-9
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
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artemisinin CAS NO.63968-64-9
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63968-64-9 Usage

Toxic grading

 Poisoning

Storage and transportation characteristics

Ventilation, low temperature and dry;

Flammability and Hazardous properties

 it is combustible with combustion producing irritating fumes

Uses

An antimalarial agent that inhibits VEGF expression and NOS2.

Drugs for treatment of malaria

Artemisinin is the drug for the treatment of malaria with the most excellent efficacy, being a kind of sesquiterpene lactone containing peroxide group extracted from the traditional Chinese medicine Artemisia annua. It is characterized with high efficiency, rapid efficacy, clearing summer-heat, clearing deficiency heat, protozoa-killing effect and low toxicity. Currently, the efficacy of the artemisinin-based combination therapy (ACT) for the treatment of malaria worldwide has reached over 90%. ACT has been already widely applied to the treatment of malaria in many countries around the world.
It has a strong and rapid killing effect on the erythrocytic stage of plasmodium, being able to rapidly control the clinical seizures and symptoms. Meanwhile, it also has prominent efficacy in the treatment of chicken coccidiosis, Mycoplasma Suis, toxoplasmosis, weakness and fever, damp heat jaundice, tertian malaria, falciparum malaria, cerebral malaria and chloroquine malaria.
Artemisinin was first successfully developed by Chinese scientists, being effective monomer originated from the folk malaria-treatment herbs Artemisia annua. China is one of the major resource countries for the growth of such plants. The demands for research and development originated from the Vietnam War in 1960s when Malaria parasites had been resistant to special drug chloroquine at that time. In Vietnam War, many soldiers are not killed in the war, but instead died of malaria.
Because of the presence of artemisinin resistance in the border areas of Cambodia and Thailand, the World Health Organization advocates the use of combinations rather than monomeric formulation. In this environment, the world's first artemisinin-based compound antimalarial drug-compound artemether has been successfully developed in China. However, due to the lack of attention on the importance of intellectual property of Chinese pharmaceutical companies, currently in the world, only Novartis Company has the authority of foreign selling of artemether compound that has been recognized by the World Health Organization. The Novartis Company has offered the drug to the WHO at the cost price, wining the wide acclaim from international community. However, in this trade war, China can only play a role of major drug producing countries.

Acute toxicity

Intraperitoneal-rat LD50: 2571 mg/kg; Abdominal-mouse LD50: 1558 mg/kg

Fire extinguishing agent

dry powder, foam, sand, carbon dioxide, mist water

Uses

Active antimalarial constituent of the tradional Chinese medicinal herb Artemisia annua L., Compositae, which has been known for almost 2000 years as Qinghao. Antimalarial

Biological Activity

Antimalarial agent; interacts with heme to produce carbon-centred free radicals, causes protein alkylation and damages parasite microorganelles and membranes. Also selectively inhibits the P-type ATPase (PfATP6) of Plasmodium falciparum (K i ~ 150 nM). Displays antiangiogenic effects in mouse embryonic stem cell-derived embryoid bodies.

Uses

Artemisia annua is used as antimalarial drugs. Clinical application has shown that artemisinin and its derivatives have special effects on treating the malaria and falciparum malaria, especially artemisinin which has stronger killing effect on Plasmodium falciparum intracellular phorozoon than other artemisinin drugs, characterized by high efficiency, rapid efficacy, low toxicity and no cross-resistance with chloroquine, etc. It can be not only used for treatment, but also for emergency treatment. It is applicable to a variety of malaria such as falciparum malaria, vivax malaria, anti-chloroquine malaria and cerebral malaria, including dangerous type.
The most notable drug is dihydroartemisinin and its tablets. This drug has its antimalarial effect be 10 times as strong as artemisinin with the recurrence rate of only 1.95%, thus having been rated as China's top ten scientific and technological achievements in 1992. Artemisinin and its derivatives not only are excellent antimalarial drugs, but also have potentially attractive prospect in the treatment of other diseases. Animal experiments have found that artemisinin treatment of Clonorchis sinensis can achieve a rate of pest control being up to 100%; treatment of animal schistosomiasis can achieve a pest control rate of 33.8-99.3%. Application of artemisinin treatment of discoid lupus erythematosus can achieve a total effective rate of 90%. Its efficacy in the treatment of dengue fever is significantly better than morphine biguanide and other western medicines. Immunologists have also found that artemisinin can significantly improve the lymphocyte transformation rate and enhance the immune function of antibodies. People haven’t found toxic effect of this product on the heart, liver and kidney. People haven’t observed any significant side effects in clinical practice.

Chemical properties

It appears as colorless needle crystal with a melting point being156-157 °C. It is easily soluble in chloroform, acetone, ethyl acetate and benzene, being soluble in methanol, ethanol and insoluble in water.

Chemical Properties

Crystalline Solid

Category

 Toxic substances

Definition

ChEBI: A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.

Production method

It can be extracted from the leaves of Artemisia annua L. (Compositae). In addition to artemisinin, China also produces both artemether and sodium artemisinin.
InChI:InChI=1/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14+,15-/m1/s1

63968-64-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (69532)  Artemisinin  analytical standard 63968-64-9 69532-10MG 679.77CNY Detail
USP (1042747)  Artemisinin  United States Pharmacopeia (USP) Reference Standard 63968-64-9 1042747-20MG 14,500.98CNY Detail
TCI America (A2118)  Artemisinin  >97.0%(HPLC) 63968-64-9 5g 390.00CNY Detail
TCI America (A2118)  Artemisinin  >97.0%(HPLC) 63968-64-9 1g 160.00CNY Detail

63968-64-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (+)-artemisinin

1.2 Other means of identification

Product number -
Other names qinghausu

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:63968-64-9 SDS

63968-64-9Synthetic 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

(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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; magnesium oxide; Rh2(fb)4 In dichloromethane for 24h; Heating;96%
4α-hydroperoxy-amorph-5-en-12-oic acid
85031-60-3

4α-hydroperoxy-amorph-5-en-12-oic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

(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
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
ConditionsYield
With oxygen; trifluoroacetic acid In toluene Flow reactor; chemoselective reaction;A 81%
B 7%
4-chloro-3-nitrobenzoate
96-99-1

4-chloro-3-nitrobenzoate

7β-hydroxyartemisinin

7β-hydroxyartemisinin

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;75%
4α-hydroperoxy-amorph-5-en-12-oic acid
85031-60-3

4α-hydroperoxy-amorph-5-en-12-oic acid

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; copper(I) triflate at 20℃; Temperature;65%
(3R)-dihydroarteannuin B acid methyl carbonate
1267472-30-9

(3R)-dihydroarteannuin B acid methyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;62.2%
(3R)-dihydroarteannuin B acid ethyl carbonate
1267472-33-2

(3R)-dihydroarteannuin B acid ethyl carbonate

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

C12H13O2(CH3)3(O)(OO)

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

(3R)-dihydroarteannuin B acid benzyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;59.2%
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

arteanniun H
207446-83-1

arteanniun H

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

(3R)-dihydroarteannuin B acid 2,2,2-trichloroethyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;58.7%
(3R)-dihydroarteannuin B acid phenyl carbonate
1267472-37-6

(3R)-dihydroarteannuin B acid phenyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;58.4%
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

(4R,4aS,7R,8S)-4,7-Dimethyl-8-(3-oxo-butyl)-4,4a,5,6,7,8-hexahydro-isochromen-3-one
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
ConditionsYield
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
(3R)-dihydroarteannuin B acid 2-chloroethyl carbonate
1267472-43-4

(3R)-dihydroarteannuin B acid 2-chloroethyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;54.9%
(3R)-dihydroarteannuin B acid propyl carbonate
1267472-39-8

(3R)-dihydroarteannuin B acid propyl carbonate

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; 5,10,15,20-tetraphenyl-21H,23H-porphine In dichloromethane at -10 - 20℃; for 22h; Photochemical reaction;54.5%
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
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%
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With porphyrin; trifluoroacetic acid In toluene at 25℃; Temperature; Reagent/catalyst; Irradiation;50%
(+)-deoxoartemisinin
126189-95-5

(+)-deoxoartemisinin

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate49%
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

(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
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

arteanniun H
207446-83-1

arteanniun H

Conditions
ConditionsYield
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%
5α-hydroperoxy-amorph-5-en-12-oic acid methyl ester
85031-63-6

5α-hydroperoxy-amorph-5-en-12-oic acid methyl ester

A

C12H13O2(CH3)3(O)(OO)
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

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

C

(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
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

(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
ConditionsYield
In chloroform-d1 for 2556.75h; Further byproducts given;A 3%
B 40%
C 4%
D n/a
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

(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
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

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

arteanniun H
207446-83-1

arteanniun H

Conditions
ConditionsYield
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%
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
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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
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%
(R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester
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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
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%
dehydroqinghaosu
101020-89-7

dehydroqinghaosu

A

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

C12H13O2(CH3)3(O)(OO)

B

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

(+)-9-epiartemisinin

C

9β-hydroxydeoxy-11-epi-artemisinin

9β-hydroxydeoxy-11-epi-artemisinin

D

9β-hydroxy-11-epi-artemisinin

9β-hydroxy-11-epi-artemisinin

Conditions
ConditionsYield
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%
artemisinic acid
80286-58-4

artemisinic acid

A

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

C12H13O2(CH3)3(O)(OO)

B

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one
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
ConditionsYield
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;
(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid
116399-93-0

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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
With ozone; trifluoroacetic acid 1.) MeOH, -78 deg C, 2.) CHCl3, H2O; Yield given. Multistep reaction;
(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid
116399-93-0

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

A

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

C12H13O2(CH3)3(O)(OO)

B

2-deoxyartemisinin
72826-63-2

2-deoxyartemisinin

Conditions
ConditionsYield
With oxygen; ozone; trifluoroacetic acid 1.) CH2Cl2, -78 deg C, 2.) CDCl3; Yield given. Multistep reaction. Yields of byproduct given;
2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane
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

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

C12H13O2(CH3)3(O)(OO)

B

2-deoxyartemisinin
72826-63-2

2-deoxyartemisinin

Conditions
ConditionsYield
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

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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
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

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

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

C12H13O2(CH3)3(O)(OO)

Conditions
ConditionsYield
Yield given. Multistep reaction;
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

dihydroartemisinin
71939-50-9

dihydroartemisinin

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
ConditionsYield
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℃;
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

dihydroartemisinin
71939-50-9

dihydroartemisinin

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

2-deoxyartemisinin
72826-63-2

2-deoxyartemisinin

Conditions
ConditionsYield
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%
succinic acid anhydride
108-30-5

succinic acid anhydride

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

C12H13O2(CH3)3(O)(OO)

artesunate
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

7β-hydroxyartemisinin

7β-hydroxyartemisinin

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

9α-hydroxyartemisinin

9α-hydroxyartemisinin

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

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

C12H13O2(CH3)3(O)(OO)

A

(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
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

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

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

Conditions
ConditionsYield
With sulfuric acid for 0.166667h;A n/a
B 90%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

acetyl chloride
75-36-5

acetyl chloride

dihydroartemisinin acetate
75887-51-3

dihydroartemisinin acetate

Conditions
ConditionsYield
Stage #1: C12H13O2(CH3)3(O)(OO) With sodium tetrahydroborate
Stage #2: acetyl chloride With pyridine
90%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

6a-hydroxy-artemisinin

6a-hydroxy-artemisinin

Conditions
ConditionsYield
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%
dehydroqinghaosu
101020-89-7

dehydroqinghaosu

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

C12H13O2(CH3)3(O)(OO)

C30H42O10

C30H42O10

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

(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
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
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 25h; Ambient temperature;87%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

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

(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
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

9-fluoroartemisinin
1037585-91-3

9-fluoroartemisinin

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
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

(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
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

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
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
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 7h;79%
propan-1-ol
71-23-8

propan-1-ol

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

C12H13O2(CH3)3(O)(OO)

C18H30O5

C18H30O5

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

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

3α-hydroxydeoxyartemisinin

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

2-deuteriodihydroqinghaosu

2-deuteriodihydroqinghaosu

Conditions
ConditionsYield
With sodium borodeuteride In methanol for 1h; Reduction;77%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

C16H23F3O5

C16H23F3O5

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

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

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

Conditions
ConditionsYield
With sulfuric acid In methanol75%
With iron(III) chloride In diethyl ether for 1.5h;
With trifluoroacetic acid In methanol Heating;
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

10-deoxoartemisinin

10-deoxoartemisinin

Conditions
ConditionsYield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran75%
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
pentan-1-ol
71-41-0

pentan-1-ol

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

C12H13O2(CH3)3(O)(OO)

C20H34O5

C20H34O5

Conditions
ConditionsYield
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%
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

ethylene glycol
107-21-1

ethylene glycol

C18H30O6

C18H30O6

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 17h; Reflux;74%
methanol
67-56-1

methanol

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

C12H13O2(CH3)3(O)(OO)

(R)-methyl 2-((3R,6R,9aR)-9a-formyl-3-methoxy-3,6-dimethyloctahydro-3H-benzo[c][1,2]dioxepin-9-yl)propanoate
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
ConditionsYield
With trifluoroacetic acid for 5h; Reflux;73%
With sulfuric acid for 3h; Yield given;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

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

C12H13O2(CH3)3(O)(OO)

C19H32O6

C19H32O6

Conditions
ConditionsYield
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%

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