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

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.

C1O-modified artemisinin derivatives: Efficient heme-alkylating agents

(Chemical Equation Presented) Discussion is reopened regarding C10-substituted derivatives of the peroxide-based antimalarial agent artemisinin (see picture); they are shown to react readily with iron(II)-heme to provide heme-drug adducts in high yields.

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

Photophysics of a new photosensitizer with high quantum yield of singlet oxygen generation and its application to stereo-selective synthesis of (+)-deoxoartemisinin

A new photo-catalyst of [5,10,15-triphenyl-20-(4-methoxycarbonylphenyl)-porphyrin] platinum was synthesized and its photophysical study revealed that it had a high quantum yield of singlet oxygen generation. As an application study, a stereo-specific synt

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.

Synthesis of (+)-Artemisinin and (+)-Deoxoartemisinin from arteannuin B and arteannuic acid

(+)-Artemisinin and (+)-Deoxoartemisinin were prepared for the first time from arteannuin B. The synthetic route is short and efficient, making use of the prior art for the final photo-oxygenation/cyclization reaction. A convergent route to each of the above-named products from arteannuic acid is also described. A novel oxidative lactonization reaction was developed for this sequence.

AN EFFICIENT PARTIAL SYNTHESIS OF (+)-ARTEMISININ AND (+)-DEOXOARTEMISININ

Arteannuic acid and arteannuin B are separately convertible into intermediate 8, which is transformed by four of five high-yielding steps into the title anti-malarial sesquiterpene peroxides. Key Words: Artemisinin, Deoxoartemisinin, Arteannuin B, Arteannuic Acid, Singlet Oxygen, Reducitive Elimination, Ketalization, Allylic Oxidation.

An Efficient Synthesis of Qinghaosu and Deoxoqinghaosu from Arteannuic Acid

Photo-oxidation of cyclic enol ether (3) and successive treatments with trimethylsilyl trifluoromethanesulphonate (TfOTMS) afforded three compounds, deoxoqinghaosu (4), (5), and (6); oxidation of (4) with RuO4 gave qinghaosu (1).

A SHORT AND STEREOSPECIFIC SYNTHESIS OF (+)-DEOXOARTEMISININ AND (-)-DEOXODESOXYARTEMISININ

The synthesis of (+)-deoxoartemisinin and (-)-deoxodesoxyartemisinin was achieved either from artemisinic acid or from artemisinin.