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71939-50-9

Basic Information
CAS No.: 71939-50-9
Name: Dihydroartemisinin
Article Data: 54
Cas Database
Molecular Structure:
Molecular Structure of 71939-50-9 (Dihydroartemisinin)
Formula: C15H24O5
Molecular Weight: 284.353
Synonyms: Cotecxin;DHQHS 2;Dihydroqinghaosu;Salaxin;Santecxin;
Density: 1.24 g/cm3
Melting Point: 144-149 °C
Boiling Point: 375.6 °C at 760 mmHg
Flash Point: 181 °C
Appearance: white solid
Safety: 22-24/25
PSA: 57.15000
LogP: 2.18670
Synthetic route
63968-64-9

C12H13O2(CH3)3(O)(OO)

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%
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;
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
ConditionsYield
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.
71939-50-9

dihydroartemisinin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine; dmap at 0 - 20℃; for 3h;99%
108-24-7

acetic anhydride

71939-50-9

dihydroartemisinin

75887-51-3

dihydroartemisinin acetate

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

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

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.