126189-95-5

Basic information

• Product Name: deoxoartemisinin
• Synonyms: deoxoartemisinin;(3R,9R,10aR,10bR)-Decahydro-3α,6β,9-trimethyl-10aH-9β,10bβ-epidioxypyrano[4,3,2-jk][2]benzoxepin
• CAS NO: 126189-95-5
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.3487
• Mol File: 126189-95-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 373°Cat760mmHg
• Flash Point: 179.4°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.000305mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: deoxoartemisinin(CAS DataBase Reference)
• NIST Chemistry Reference: deoxoartemisinin(126189-95-5)
• EPA Substance Registry System: deoxoartemisinin(126189-95-5)

Safety Data

• Hazardous Substances Data: 126189-95-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H24O4/c1-9-4-5-11-10(2)8-16-13-15(11)12(9)6-7-14(3,17-13)18-19-15/h9-13H,4-8H2,1-3H3/t9-,10+,11+,12+,13-,14?,15+/m1/s1

Upstream product

• 126189-96-6 4-((4R,4aS,7R)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one 
• 63968-64-9 artemisinin 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 
• 126189-96-6 4-((4R,4aS,7R,8S)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one 
• 127924-95-2 (1R,2S,3R,6S)-1-Hydroperoxy-6-((R)-2-hydroxy-1-methyl-ethyl)-3-methyl-2-(3-oxo-butyl)-cyclohexanecarbaldehyde 
• 141039-66-9 2-(2-(3-(3-hydroxy-(2R)-methylpropyl)-2-methoxymethoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 137288-63-2 4α-hydroperoxy-amorph-5-en-12-ol 
• 50906-56-4 (1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^1,5.0^12,14]tetradecan-3-one 
• 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 
• 87206-33-5 (3R)-dihydroarteannuin B 
• 111399-00-9 (3R,3aS,6R,6aS,7aS)-3,6-dimethyl-7a-formyl-7-(3-oxobutyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one 
• 111399-02-1 (3R,3aS,6R,7S,7aS)-3,6-dimethyl-7a-formyl-7-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-hexahydrobenzo[1,2-b]furan-2(3H)-one 
• 141039-67-0 2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane 
• 161022-41-9 dihydroartemisinic acid 

Downstream Products

• 63968-64-9 artemisinin 
• 104992-28-1 (-)-deoxodesoxyartemisinin 
• 176022-28-9 1-oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanol formyl ester]-cyclohexane 
• 63968-64-9 C₁₂H₁₃O₂(CH₃)3(O)(OO) 

Relevant articles and documents

Synthesis and antimalarial activity of (+)-deoxoartemisinin

(+)-Deoxoartemisinin (2), a new and more active antimalarial agent, was successfully prepared from artemisinin in one step using NaBH4 and BF3·Et2O in THF. (-)-Deoxodeoxyartemisinin (5), a potential metabolite of deoxoartemisinin, was also prepared either from 2 or from artemisinic acid. 2 shows 8-fold increased antimalarial activity in vitro against chloroquine-resistant malaria as compared to artemisinin (1). Compound 2 possesses superior in vivo antimalarial activity to 1.

Potent antimalarial 1,2,4-trioxanes through perhydrolysis of epoxides

Perhydrolysis of a sterically congested multifunctional epoxide was achieved in ethereal H2O2 with the aid of a recently developed Mo catalyst. The resulting hydroperoxide cyclized to give a 1,2,4-trioxane, which could be readily elaborated into qinghaosu and a range of novel analogues. Some of the compounds with two such trioxane moieties showed in vitro antimalarial activity comparable to or even better than that of artesunate or chloroquine. Molybdenum magic: Facile perhydrolysis of a highly hindered epoxide was achieved with the aid of a molybdenum catalyst. The resulting hydroperoxide was readily converted into a 1,2,4-trioxane, from which natural qinghaosu (QHS, or artemisinin; see scheme) and a range of analogues were constructed. Some of the newly accessed trioxanes showed in vitro antimalarial activity comparable to or even better than that of chloroquine and artesunate. Copyright

The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid

Three of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Δ4,5 double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions.