Dihydroartemisinin supplier | CasNO.71939-50-9

Name
Dihydroartemisinin
EINECS
CAS No. 71939-50-9
Article Data54
CAS DataBase
Density 1.24 g/cm³
Solubility
Melting Point 144-149 °C
Formula C₁₅H₂₄O₅
Boiling Point 375.6 °C at 760 mmHg
Molecular Weight 284.353
Flash Point 181 °C
Transport Information
Appearance white solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Cotecxin;DHQHS 2;Dihydroqinghaosu;Salaxin;Santecxin;
PSA 57.15000
LogP 2.18670

Synthetic route

: 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%

: 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;

: 255730-31-5
10α-(4-benzylpiperazin-1-yl)-10-deoxoartemisinin

A: 71939-50-9
dihydroartemisinin

B: 1093625-96-7
(R)-2-[(3S,4R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionaldehyde

C: (3aS,4R,7S,7aR)-4-Methyl-7-((R)-1-methyl-2-oxo-ethyl)-hexahydro-benzofuran-7a-carbaldehyde

Conditions

Conditions	Yield
With hemin; L-Cysteine In water; acetonitrile at 23℃; for 24h; pH=7.4; Product distribution; Further Variations:; Reagents;	A 6 % Spectr. B 4 % Spectr. C 6 % Spectr.

...Expand

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

: 71939-50-9
dihydroartemisinin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid; oxygen / toluene / -20 - 10 °C / Flow reactor; Photolysis; Irradiation 2: sodium tetrahydroborate; lithium chloride; lithium carbonate; ethanol View Scheme

: 71939-50-9
dihydroartemisinin

: 98-88-4
benzoyl chloride

: 82596-25-6
10α-dihydroartemisinyl benzoate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	100%
With pyridine In dichloromethane at 0℃; for 16h;	100%
With pyridine In dichloromethane at 20℃; for 16h;	97%

: 71939-50-9
dihydroartemisinin

: 98-88-4
benzoyl chloride

: 163381-14-4
(5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 16h;	100%
With pyridine In dichloromethane at 0℃; for 16h; Inert atmosphere;	91%

: 108-24-7
acetic anhydride

: 71939-50-9
dihydroartemisinin

: 221890-91-1
O-acetyldihydroartemisinin

Conditions

Conditions	Yield
With pyridine; dmap at 0 - 20℃; for 3h;	99%

: 108-24-7
acetic anhydride

: 71939-50-9
dihydroartemisinin

: 75887-51-3
dihydroartemisinin acetate

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃;	98%
In pyridine at 20℃; for 8h;	92%
With pyridine; dmap In dichloromethane at 25℃; Acetylation;	87%
With pyridine; dmap at -78 - 20℃; Inert atmosphere;

: 700-57-2
1-adamantanol

: 71939-50-9
dihydroartemisinin

: C25H38O5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -10 - -5℃; for 2h;	97%

: 71939-50-9
dihydroartemisinin

: 100-51-6
benzyl alcohol

: 10β-(phenylmethoxy)dihydroartemisinin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 6h;	96%

: 71939-50-9
dihydroartemisinin

: 82596-30-3
9,10-dehydrodihydroartemisinin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; Darkness;	95%
With phosphorus pentoxide In dichloromethane	90%
With boron trifluoride diethyl etherate In diethyl ether at 20℃; for 18h;	90%

: 71939-50-9
dihydroartemisinin

: 122-04-3
4-nitro-benzoyl chloride

A: C22H27NO8

B: 12α-dihydroartemisinyl 4'-nitrobenzoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane Cooling;	A n/a B 95%

...Expand

: 71939-50-9
dihydroartemisinin

: 122-04-3
4-nitro-benzoyl chloride

: 12α-dihydroartemisinyl 4'-nitrobenzoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	94%
With triethylamine In dichloromethane at 20℃;	82%

: 71939-50-9
dihydroartemisinin

: 75-36-5
acetyl chloride

: 75887-51-3
dihydroartemisinin acetate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h;	94%

: 75-77-4
chloro-trimethyl-silane

: 71939-50-9
dihydroartemisinin

: 10-trimethylsylylether-artemisinin

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 0.0833333h;	94%

: 71939-50-9
dihydroartemisinin

: 107-19-7
propargyl alcohol

: C17H24O5

Conditions

Conditions	Yield
With 12-tungstophosphoric acid hydrate In dichloromethane at 20℃; Inert atmosphere;	94%

: 75-77-4
chloro-trimethyl-silane

: 71939-50-9
dihydroartemisinin

: 140658-34-0
10β-(trimethylsilyloxy)dihydroartemisinin

Conditions

Conditions	Yield
With pyridine for 24h; Ambient temperature;	93%
With pyridine at 0℃; for 1.25h;	81%
In pyridine at 0℃; for 1.25h;	76%

: 71939-50-9
dihydroartemisinin

: 619-66-9
4-Carboxybenzaldehyde

: 1009081-17-7
C23H28O7

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	93%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 25h;	40.46%

: 108-30-5
succinic acid anhydride

: 71939-50-9
dihydroartemisinin

: butanedioic acid [3R-(3α,5aβ,6β,8aβ,9α,12β,12aR*)]-mono(decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl) ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 18℃; for 4h; Concentration;	91%
With piperidine In dichloromethane at 0 - 25℃; for 2h;	85%
With pyridine for 168h; Ambient temperature;	20 mg

: 108-30-5
succinic acid anhydride

: 71939-50-9
dihydroartemisinin

: 88495-63-0
artesunic acid

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 2h;	91%
With dmap In dichloromethane at 20℃;

: 75-77-4
chloro-trimethyl-silane

: 71939-50-9
dihydroartemisinin

: 255731-10-3
10α-(trimethylsilyloxy)dihydroartemisinin

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Cooling with ice;	90%
With triethylamine In dichloromethane at 0℃; for 1.5h;	83%
With triethylamine In dichloromethane

: 71939-50-9
dihydroartemisinin

: 540-51-2
2-bromoethanol

: 101834-30-4
1-bromo-2-(10β-dihydroartemisinoxy)ethane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;	90%
With boron trifluoride diethyl etherate In dichloromethane at 0℃;	87%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 6h;	71%

: 112-92-5
1-octadecanol

: 71939-50-9
dihydroartemisinin

A: C33H60O5

B: C33H60O5

Conditions

Conditions	Yield
With acidic catalyst In dichloromethane at 0 - 10℃;	A 90% B n/a

...Expand

: 71939-50-9
dihydroartemisinin

: 121-90-4
m-nitrobenzoic acid chloride

A: 12α-dihydroartemisinyl 3'-nitrobenzoate

B: C22H27NO8

Conditions

Conditions	Yield
With triethylamine In dichloromethane Cooling;	A 90% B n/a

...Expand

: 112-16-3
n-dodecanoyl chloride

: 71939-50-9
dihydroartemisinin

A: 12α-dihydroartemisinyl laurate

B: C27H46O6

Conditions

Conditions	Yield
With triethylamine In dichloromethane Cooling;	A 90% B n/a

...Expand

: 66411-55-0
2,3-(Methylenedioxy)benzoyl chloride

: 71939-50-9
dihydroartemisinin

A: C23H28O8

B: C23H28O8

Conditions

Conditions	Yield
With triethylamine In dichloromethane Cooling;	A 90% B n/a

...Expand

: 71939-50-9
dihydroartemisinin

: 112-67-4
n-hexadecanoyl chloride

A: C31H54O6

B: 12α-dihydroartemisinyl palmitate

Conditions

Conditions	Yield
With triethylamine In dichloromethane Cooling;	A n/a B 90%

...Expand

: 55-22-1
pyridine-4-carboxylic acid

: 71939-50-9
dihydroartemisinin

: C21H27NO6

Conditions

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4.5h;	90%

: 59-67-6
nicotinic acid

: 71939-50-9
dihydroartemisinin

: C21H27NO6

Conditions

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4.5h;	90%

: 6908-41-4
4-(methoxycarbonyl)benzyl alcohol

: 71939-50-9
dihydroartemisinin

: 216963-48-3
methyl p-<(10-dihydroartemisininoxy)methyl>benzoate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;	89%
With chloro-trimethyl-silane Ambient temperature;	85%

: 71939-50-9
dihydroartemisinin

: 627-18-9
1-bromo-3-propanol

: 165068-34-8
1-bromo-3-(10β-dihydroartemisinoxy)propane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃;	89%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Etherification;	60%
With boron trifluoride diethyl etherate In diethyl ether for 6h;	52%

: 140-10-3
(E)-3-phenylacrylic acid

: 71939-50-9
dihydroartemisinin

: (3R,5aS,6R,8aS,9R,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl cinnamate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	89%

: 71939-50-9
dihydroartemisinin

: 540-51-2
2-bromoethanol

: C17H27BrO5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 14h; Concentration; Cooling with ice;	87.5%

Dihydroartemisinin Chemical Properties

Chemical Name: Dihydroartemisinin
CAS No.: 71939-50-9
Molecular Formula: C₁₅H₂₄O₅
Molecular Weight: 284.35 g/mol
Melting Point: 144-149°C
Density: 1.24 g/cm³
Flash Point: 181 °C
Boiling Point: 375.6 °C at 760 mmHg
Storage temp.: 2-8°C
Following is the structure of Dihydroartemisinin (CAS No.:71939-50-9):

Product Categories about Dihydroartemisinin (CAS No.:71939-50-9) are Miscellaneous Natural Products ; Intermediates & Fine Chemicals ; Metabolites & Impurities ; Pharmaceuticals
The chemical synonymous of Dihydroartemisinin (CAS No.:71939-50-9) are (3r,5as,6r,8as,9r,10r,12r,12ar)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j]-1,2-benzodioxepin-10-ol ; Dihydroarteminisin ; Dihydroartemisin ; (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-ol ; Alaxin ; b-Dihydroartemisinin ; Cotecxin

Dihydroartemisinin Specification

Dihydroartemisinin (CAS No.:71939-50-9) is a drug used to treat malaria. Dihydroartemisinin is the active metabolite of all artemisinin compounds (artemisinin, artesunate, artemether, etc.) and is also available as a drug in itself. The lactone of artemisinin could selectively be reduced with mild hydride-reducing agents, such as sodium borohydride, potassium borohydride, and lithium borohydride to dihydroartemisinin (a lactol) in over 90% yield. It is a novel reduction, because normally lactone cannot be reduced with sodium borohydride under the same reaction conditions. Reduction with LiAlH4 leads to some rearranged products. It was surprising to find that the lactone was reduced, but that the peroxy group survived. However, the lactone of deoxyartemisinin resisted reduction with sodium borohydride and could only be reduced with isobutylaluminium hydride to the lactol, (deoxydihydroartimisinin). These results show that the peroxy group assists the reduction of lactone with sodium borohydride to a lactol, but not to the alcohol which is the over-reduction product. No clear evidence for this reduction process exists.

Product Name

Dihydroartemisinin

Synthetic route

Dihydroartemisinin Chemical Properties

Dihydroartemisinin Specification

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