Arteether supplier | CasNO.75887-54-6

Name
Arteether
EINECS
CAS No. 75887-54-6
Article Data14
CAS DataBase
Density 1.16 g/cm³
Solubility
Melting Point 80-820 °C
Formula C₁₇H₂₈O₅
Boiling Point 372.4 °C at 760 mmHg
Molecular Weight 312.406
Flash Point 146 °C
Transport Information
Appearance white crystalline solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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)-;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;	A n/a B 72%

...Expand

: 122-51-0
orthoformic acid triethyl ester

: 81496-81-3
dihydroartesiminin

: 75887-54-6
artemotil

Conditions

Conditions	Yield
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

: 481-05-0, 1750-99-8, 17367-67-8, 46961-87-9, 96847-33-5, 103617-15-8
artemisin

: 75887-54-6
artemotil

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 64-17-5
ethanol

: 82596-30-3
9,10-dehydrodihydroartemisinin

A: 75887-54-6
artemotil

B: 11-epi-β-arteether

Conditions

Conditions	Yield
With triphenylphosphine hydrobromide In dichloromethane for 8h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 64-17-5
ethanol

: 71939-50-9
dihydroartemisinin

: 75887-54-6
artemotil

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;

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

: 75887-54-6
artemotil

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

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

A: 82534-75-6
Alpha-Arteether

B: 75887-54-6
artemotil

Conditions

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 122-51-0
orthoformic acid triethyl ester

: dihydroartesiminin

: 75887-54-6
artemotil

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water Flow reactor;

: 63968-64-9, 113472-97-2, 119241-68-8
artemisinin

: 75887-54-6
artemotil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; ethanol / Flow reactor 2: hydrogenchloride / water; ethanol / Flow reactor View Scheme

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

: 75887-54-6
artemotil

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogen; Lindlar's catalyst In ethanol Ambient temperature;	69%

: 75887-54-6
artemotil

: 130778-40-4
9β-hydroxyarteether

Conditions

Conditions	Yield
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

Conditions	Yield
Streptomyces lavendulae fermentation;	A 32.1% B 10.7% C 10.7%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Arteether Chemical Properties

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

Arteether 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.

Arteether 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.

Product Name

Arteether

Synthetic route

Arteether Chemical Properties

Arteether Uses

Arteether Specification

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