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75887-54-6

Basic Information
CAS No.: 75887-54-6
Name: Arteether
Molecular Structure:
Molecular Structure of 75887-54-6 (Arteether)
Formula: C17H28O5
Molecular Weight: 312.40
Synonyms: 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin,10-ethoxydecahydro-3,6,9-trimethyl-, [3R-(3a,5ab,6b,8ab,9a,10a,12b,12aR*)]-;Artemotil;Dihydroqinghaosu ethyl ether;NSC 665971;SM 227;b-Arteether;3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin,10-ethoxydecahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-;
EINECS:
Density: 1.16 g/cm3
Melting Point: 80-820 °C
Boiling Point: 372.4 °C at 760 mmHg
Flash Point: 146 °C
Solubility:
Appearance: white crystalline solid
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 46.15000
LogP: 3.23090
Synthetic route
108739-44-2

3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide

75887-54-6

artemotil

Conditions
ConditionsYield
chloromethyldimethylsilane In ethanol at 20 - 23℃; for 0.666667 - 1.83333h; Acidic conditions;80.5%
Stage #1: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; chloromethyldimethylsilane In ethanol at 20 - 23℃; for 2h; Acidic conditions;
Stage #2: chloromethyldimethylsilane In ethanol at 20℃; for 2h; Acidic conditions;
74%
Stage #1: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; toluene-4-sulfonic acid In ethanol at 20 - 23℃; for 4h; Acidic conditions;
Stage #2: toluene-4-sulfonic acid In ethanol at 20℃; for 4h; Acidic conditions;
53%

10-ethoxy-9-bromodihydroartemisinin

75887-54-6

artemotil

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); n-Bu3SnH4 In toluene for 20h; Heating;75%
64-17-5

ethanol

71939-50-9

dihydroartemisinin

A

82534-75-6

Alpha-Arteether

B

75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;A n/a
B 72%
122-51-0

orthoformic acid triethyl ester

81496-81-3

dihydroartesiminin

75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: orthoformic acid triethyl ester; dihydroartesiminin In ethanol at 20℃; for 0.25h;
Stage #2: With acetyl chloride In ethanol at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In ethanol; water at 0 - 5℃; for 2h;
71.38%
108739-44-2

3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide

75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: artemisin; D-Galactose In ethanol at 20 - 23℃; for 1.58333h;
Stage #2: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; chloromethyldimethylsilane In ethanol for 2h; Acidic conditions;
62%
64-17-5

ethanol

71939-50-9

dihydroartemisinin

A

82534-75-6

Alpha-Arteether

B

75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate
With chloro-trimethyl-silane for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chloro-trimethyl-silane In ethanol at 20 - 23℃; for 1h;
64-17-5

ethanol

82596-30-3

9,10-dehydrodihydroartemisinin

A

75887-54-6

artemotil

B

11-epi-β-arteether

Conditions
ConditionsYield
With triphenylphosphine hydrobromide In dichloromethane for 8h; Ambient temperature; Yield given. Yields of byproduct given;
64-17-5

ethanol

71939-50-9

dihydroartemisinin

75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;
63968-64-9

C12H13O2(CH3)3(O)(OO)

75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / NaBH4 / methanol / 1 h / 0 °C
2: BF3*Et2O / benzene / 1 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 87 percent / NaBH4
2: 80 percent / P2O5 / CH2Cl2 / 0.5 h / Ambient temperature
3: triphenylphosphine hydrobromide / CH2Cl2 / 8 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 79 percent / sodium borohydride / methanol / 3 h / 0 - 5 °C
2: 72 percent / BF3*Et2O / benzene / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / methanol
2: BF3*OEt2
View Scheme
82596-30-3

9,10-dehydrodihydroartemisinin

75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. Br2
2: 70 percent / BF3*Et2O / CHCl3 / 10 h / 50 °C
3: 75 percent / n-Bu3SnH4, AIBN / toluene / 20 h / Heating
View Scheme

9-bromodihydroartemisinin

75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / BF3*Et2O / CHCl3 / 10 h / 50 °C
2: 75 percent / n-Bu3SnH4, AIBN / toluene / 20 h / Heating
View Scheme
71939-50-9

dihydroartemisinin

75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / P2O5 / CH2Cl2 / 0.5 h / Ambient temperature
2: triphenylphosphine hydrobromide / CH2Cl2 / 8 h / Ambient temperature
View Scheme
71939-50-9

dihydroartemisinin

122-51-0

orthoformic acid triethyl ester

75887-54-6

artemotil

Conditions
ConditionsYield
toluene-4-sulfonic acid In ethanol at 40℃; for 0.25h;
Dowex-50 In ethanol at 30℃; for 10h;
toluene-4-sulfonic acid In ethanol at 20℃; for 0.5h;
aluminum (III) chloride In ethanol at 40℃; for 0.75h; Heating / reflux;
64-17-5

ethanol

81496-81-3

dihydroartesiminin

A

82534-75-6

Alpha-Arteether

B

75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: dihydroartesiminin With dodecatungstophosphoric acid hydrate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: ethanol In dichloromethane at 20℃; for 6h; optical yield given as %de;
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

82534-75-6

Alpha-Arteether

B

75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / methanol
2.1: dodecatungstophosphoric acid hydrate / dichloromethane / 0.08 h / 20 °C
2.2: 6 h / 20 °C
View Scheme
64-17-5

ethanol

63968-64-9

C12H13O2(CH3)3(O)(OO)

A

82534-75-6

Alpha-Arteether

B

75887-54-6

artemotil

Conditions
ConditionsYield
With Trimethyl orthoacetate; sodium tetrahydroborate; cellulose sulfuric acid In tetrahydrofuran at -5 - 20℃; for 2.5h; Reagent/catalyst; Overall yield = 82 %;A n/a
B n/a
122-51-0

orthoformic acid triethyl ester

dihydroartesiminin

75887-54-6

artemotil

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Flow reactor;
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; ethanol / Flow reactor
2: hydrogenchloride / water; ethanol / Flow reactor
View Scheme
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 9,10-Dicyanoanthracene; oxygen / dichloromethane / -20 - 20 °C / UV-irradiation; Flow reactor
1.2: Flow reactor
2.1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; ethanol / Flow reactor
3.1: hydrogenchloride / water; ethanol / Flow reactor
View Scheme
75887-54-6

artemotil

112297-79-7

desoxyarteether

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol Ambient temperature;69%
75887-54-6

artemotil

130778-40-4

9β-hydroxyarteether

Conditions
ConditionsYield
for 144h; Cunninghamella elegans fermentation;41.7%
75887-54-6

artemotil

A

2α-hydroxyarteether

B

130778-43-7

14-hydroxyarteether

C

130855-38-8

9α-hydroxyarteether

Conditions
ConditionsYield
Streptomyces lavendulae fermentation;A 32.1%
B 10.7%
C 10.7%
75887-54-6

artemotil

1-((2R,3R,3aS,6R,6aS,10aS)-2-Ethoxy-3,6-dimethyl-2,3,3a,4,5,6,6a,7-octahydro-furo[3,2-i]chromen-8-yl)-ethanone

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 3h; Ambient temperature;7%
75887-54-6

artemotil

A

71939-50-9

dihydroartemisinin

B

82534-75-6

Alpha-Arteether

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 25℃; Product distribution; var. temp. and β-arteether/FeCl3 ratios;
75887-54-6

artemotil

14-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 36.23 mg / silver carbonate / benzene / 72 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
75887-54-6

artemotil

2α-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 32.1 percent / Streptomyces lavendulae fermentation
2: 19.75 mg / silver carbonate / benzene / 240 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: silver carbonate / benzene / 72 h / Ambient temperature
View Scheme
75887-54-6

artemotil

163562-60-5

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32.1 percent / Streptomyces lavendulae fermentation
2: 19.75 mg / silver carbonate / benzene / 240 h / Ambient temperature
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 36.23 mg / silver carbonate / benzene / 72 h / Ambient temperature
View Scheme
75887-54-6

artemotil

9β-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: 10.35 mg / silver carbonate / benzene / 192 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
75887-54-6

artemotil

9α-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 15.67 mg / silver carbonate / benzene / 336 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: silver carbonate / benzene / 192 h / Ambient temperature
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: silver carbonate / benzene / 336 h / Ambient temperature
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: 10.35 mg / silver carbonate / benzene / 192 h / Ambient temperature
View Scheme
75887-54-6

artemotil

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 15.67 mg / silver carbonate / benzene / 336 h / Ambient temperature
View Scheme
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Chemistry

Molecular structure of Arteether (CAS NO.75887-54-6) is:

Product Name: Arteether
CAS Registry Number: 75887-54-6
Molecular Weight: 312.40122 [g/mol]
Molecular Formula: C17H28O5
XLogP3-AA: 3.4
H-Bond Donor: 0
H-Bond Acceptor: 5
Melting Point: 80-820  °C
Surface Tension: 39.7 dyne/cm
Density: 1.16 g/cm3
Flash Point: 146 °C
Enthalpy of Vaporization: 59.52 kJ/mol
Boiling Point: 372.4 °C at 760 mmHg
Vapour Pressure: 2.06E-05 mmHg at 25°C 
Product Categories: Antimalarial;Intermediates & Fine Chemicals;Pharmaceuticals

Uses

 Arteether (CAS NO.75887-54-6) is a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases.

Specification

 Arteether , its cas register number is 75887-54-6. It also can be called (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin ; Artemotil ; Dihydroartemisinin ethyl ether ; 3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-, (3S-(3alpha,5alpha,6alpha,8aalpha,9beta,10beta,12beta,12aalpha))- ; 3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, decahydro-10-ethoxy-3,6,9-trimethyl-, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,12aR*))- . It is a white crystalline solid.