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Cas Database

81496-81-3

81496-81-3

Identification

  • Product Name:DHQHS 1

  • CAS Number: 81496-81-3

  • EINECS:617-239-7

  • Molecular Weight:284.353

  • Molecular Formula: C15H24O5

  • HS Code:

  • Mol File:81496-81-3.mol

Synonyms:3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol,decahydro-3,6,9-trimethyl-, [3R-(3a,5ab,6b,8ab,9a,10b,12b,12aR*)]-;Artenimol;DHQHS 1;alpha-Dihydroartemisinin;3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol,decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10R,12R,12aR)-;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Arctom
  • Product Description:alpha-Dihydroartemisinin ≥98%
  • Packaging:20mg
  • Price:$ 60
  • Delivery:In stock
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Relevant articles and documentsAll total 17 Articles be found

Development and validation of a liquid chromatography and ion spray tandem mass spectrometry method for the quantification of artesunate, artemether and their major metabolites dihydroartemisinin and dihydroartemisinin-glucuronide in sheep plasma

Duthaler, Urs,Keiser, Jennifer,Huwyler, Joerg

, p. 172 - 181 (2011)

Recently, promising fasciocidal activities of artesunate and artemether were described in rats and sheep. Therefore, a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed to quantify artesunate, artemether and their metabolites dihydroartemisinin and dihydroartemisinin-glucuronide in sheep plasma. Protein precipitation with methanol was used for sample workup. Reversed-phase high-performance liquid chromatography (HPLC) was performed using an Atlantis C18 analytical column with a mobile phase gradient system of ammonium formate and acetonitrile. The analytes were detected by MS/MS using selected reaction monitoring (SRM) with electrospray ionisation in the positive mode (transition m/z 267.4 → 163.0). The analytical range for dihydroartemisinin, dihydroartemisinin-glucuronide and artesunate was 10-1000 ng/ml and for artemether 90-3000 ng/ml with a lower limit of quantification of 10 and 90 ng/ml, respectively. Inter- and intra-day accuracy and precision deviations were 10%. Consistent relative recoveries (60-80%) were observed over the investigated calibration range for all analytes. All analytes were stable in the autosampler for at least 30 h (6 °C) and after three freeze and thaw cycles. The validation results demonstrated that the LC-MS/MS method is precise, accurate and selective and can be used for the determination of the artemisinins in sheep plasma. The method was applied successfully to determine the pharmacokinetic parameters of artesunate and its metabolites in plasma of intramuscularly treated sheep.

Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains

Liu, Yungen,Wong, Vincent Kam-Wai,Ko, Ben Chi-Bun,Wong, Man-Kin,Che, Chi-Ming

, p. 1561 - 1564 (2005)

(Chemical Equation Presented) Cytotoxic artemisinin derivatives have been synthesized by a modular approach of "artemisinin + linker + lipophilic alkyl carbon chain". A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC50 = 97 μM), up to 200-fold more potent cytotoxicity (IC50 = 0.46 μM) could be achieved by attachment of a C14H29 carbon chain to artemisinin via an amide linker.

Method for preparing dihydroartemisinin crude drug by single process

-

Paragraph 0046-0088, (2019/08/03)

The invention belongs to the technical field of production of dihydroartemisinin crude drugs, and particularly relates to a method for preparing a dihydroartemisinin crude drug through a single process. The method comprises the following steps: S1, dissolving artemisinin in a non-protonic solvent; S2, sequentially adding a phase transfer catalyst and a reducing agent, and performing reduction reaction on the artemisinin; S3, adjusting the pH value of the reaction system obtained in step the S2 to 5-7 with acid liquor, adding water, stirring, performing liquid separating, extracting a water phase obtained by the liquid separating with the same non-protonic solvent as in the step S1, and finally combining an organic phase obtained by the extracting with an organic phase obtained by liquid separating, washing with water, and drying; and S4, precipitating crystals from the dried organic phase obtained by the S3 in a crystallization-filter pressing-drying three-in-one crystallization device, then concentrating, filter-pressing and drying to obtain a dihydroartemisinin refined product. The invention provides the method for preparing the high-purity dihydroartemisinin crude drug, and thepurity and the yield of the dihydroartemisinin prepared by the method can reach more than 99%.

A process for preparing β - pedic ether process

-

Paragraph 0029-0030, (2018/04/21)

The invention discloses a technology for preparing beta-artemether. The technology comprises the following steps: reducing an initial raw material artemisinin in the presence of a reducing agent to generate dihydroartemisinin, and carrying out an etherification reaction on dihydroartemisinin and trimethyl orthoacetate in the presence of a catalyst to prepare beta-artemether. Experiments prove that the technology allows the content of alpha-artemether generated in the methyl etherification reaction to be smaller than 3%, the HPLC purity of the obtained beta-artemether to be improved to above 99.8%, the content of single impurities to be smaller than 0.1% respectively and the quality of the above product to accord with requirements of United States Pharmacopeia; and the total mole yield of the product by artemisinin can reach 95% or above. The technology can avoid tedious intermediate processing links in the prior art, realizes simple-operation low-cost high-yield preparation of highly pure beta-artemether, accords with industrial production demands of beta-artemether, and has industrial application values.

Facile stoichiometric reductions in flow: An example of artemisinin

Fan, Xiaolei,Sans, Victor,Yaseneva, Polina,Plaza, Dorota D.,Williams, Jonathan,Lapkin, Alexei

experimental part, p. 1039 - 1042 (2012/08/07)

Stoichiometric reduction of artemisinin to dihydroartemisinin (DHA) has been successfully transferred from batch to continuous flow conditions with a significant increase in productivity and an increase in selectivity. The DHA space-time-yield of up to 1.6 kg h-1 L-1 was attained which represents a 42 times increase in throughput compared to that of conventional batch process.

Process route upstream and downstream products

Process route

C<sub>12</sub>H<sub>13</sub>O<sub>2</sub>(CH<sub>3</sub>)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
With sodium tetrahydroborate; N-benzyl-N,N,N-triethylammonium chloride; In water; toluene; at -10 - 0 ℃; for 5h; Solvent; Inert atmosphere; Large scale;
99.6%
With sodium tetrahydroborate; In methanol; at 0 ℃;
With diisobutylaluminium hydride; at -78 ℃;
With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 2h;
With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃;
With sodium tetrahydroborate; In methanol;
With sodium tetrahydroborate; D-glucose; In 1,4-dioxane; at 20 - 30 ℃; for 2 - 2.16667h;
With sodium tetrahydroborate; D-glucose; In tetrahydrofuran; at 20 ℃; for 2.16667h;
With sodium tetrahydroborate; cation exchange resin; In 1,4-dioxane; at 20 - 35 ℃; for 0.666667 - 0.916667h;
With sodium tetrahydroborate; cation exchange resin; In tetrahydrofuran; at 20 - 35 ℃; for 0.666667 - 1.33333h;
With sodium tetrahydroborate; In methanol;
With methanol; sodium tetrahydroborate; at -10 - -5 ℃; for 3h;
98.6 g
With sodium tetrahydroborate; at 0 ℃; for 3h;
C<sub>12</sub>H<sub>13</sub>O<sub>2</sub>(CH<sub>3</sub>)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

dihydroartemisinin
71939-50-9

dihydroartemisinin

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
With lithium triethylborohydride; In tetrahydrofuran; at 2 ℃; for 0.166667h; optical yield given as %de; Inert atmosphere;
With methanol; sodium tetrahydroborate; at 0 - 5 ℃; for 2.66667h; Overall yield = 70 %; Overall yield = 1.93 g;
C<sub>12</sub>H<sub>13</sub>O<sub>2</sub>(CH<sub>3</sub>)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

C<sub>15</sub>H<sub>30</sub>O<sub>4</sub>

C15H30O4

9,10-dehydrodihydroartemisinin
82596-30-3

9,10-dehydrodihydroartemisinin

dihydroartemisinin
71939-50-9

dihydroartemisinin

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 3 ℃; for 0.166667h; Inert atmosphere;
1-(dihydroartemisinin-12α-yl)-β-D-glucopyranuronic acid
198976-06-6

1-(dihydroartemisinin-12α-yl)-β-D-glucopyranuronic acid

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
With Escherichia coli β-glucuronidase IX-A; at 37 ℃; for 2h; pH=6.8; aq. phosphate buffer; Enzymatic reaction;
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

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

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
at 10 ℃; for 24h; Solvolysis;
dihydroartemisinin
71939-50-9

dihydroartemisinin

dihydroartesiminin
81496-81-3

dihydroartesiminin

Conditions
Conditions Yield
In tetrahydrofuran; at 25 ℃; Solvent; Temperature; Thermodynamic data; Equilibrium constant; Kinetics;
In methanol; water; acetonitrile; at 10 ℃; pH=6; Temperature; pH-value; Kinetics; aq. phosphate buffer;
Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; at 0 - 5 ℃; for 3h;
85%
succinic acid anhydride
108-30-5

succinic acid anhydride

dihydroartesiminin
81496-81-3

dihydroartesiminin

artesunate
88495-63-0

artesunate

Conditions
Conditions Yield
With dmap; In 1,2-dichloro-ethane; at 45 ℃; for 6h; Reagent/catalyst; Solvent; Temperature; Industrial scale;
97%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

dihydroartesiminin
81496-81-3

dihydroartesiminin

artemotil
75887-54-6

artemotil

Conditions
Conditions Yield
orthoformic acid triethyl ester; dihydroartesiminin; In ethanol; at 20 ℃; for 0.25h;
With acetyl chloride; In ethanol; at 10 - 15 ℃;
With sodium hydrogencarbonate; In ethanol; water; at 0 - 5 ℃; for 2h;
71.38%
ethanol
64-17-5

ethanol

dihydroartesiminin
81496-81-3

dihydroartesiminin

Alpha-Arteether
82534-75-6

Alpha-Arteether

artemotil
75887-54-6

artemotil

Conditions
Conditions Yield
dihydroartesiminin; With dodecatungstophosphoric acid hydrate; In dichloromethane; at 20 ℃; for 0.0833333h;
ethanol; In dichloromethane; at 20 ℃; for 6h; optical yield given as %de;

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