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Artemisinin

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Name

Artemisinin

EINECS 1806241-263-5
CAS No. 63968-64-9 Density 1.24 g/cm3
PSA 53.99000 LogP 2.39490
Solubility N/A Melting Point 156-157 oC
Formula C15H22O5 Boiling Point 389.9oC at 760 mmHg
Molecular Weight 282.337 Flash Point 172oC
Transport Information N/A Appearance Crystalline Solid
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 63968-64-9 (Artemisinin) Hazard Symbols N/A
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;

Article Data 61

Artemisinin 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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
1267472-35-4

(3R)-dihydroarteannuin B acid benzyl carbonate

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%

A

63968-64-9

C12H13O2(CH3)3(O)(OO)

B

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
1267472-31-0

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

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%
1267472-37-6

(3R)-dihydroarteannuin B acid phenyl carbonate

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%

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 cm
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  .

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