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361593

Sigma-Aldrich

Artemisinin

98%

Synonyme(s) :

Arteannuin, Qinghaosu

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About This Item

Formule empirique (notation de Hill) :
C15H22O5
Numéro CAS:
Poids moléculaire :
282.33
Numéro MDL:
Code UNSPSC :
12352205
ID de substance PubChem :
Nomenclature NACRES :
NA.79

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Niveau de qualité

Essai

98%

Forme

solid

Activité optique

[α]20/D +76°, c = 0.5 in methanol

Pf

156-157 °C (lit.)

Spectre d'activité de l'antibiotique

parasites
viruses

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Mode d’action

enzyme | inhibits

Chaîne SMILES 

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

InChI

1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

Clé InChI

BLUAFEHZUWYNDE-NNWCWBAJSA-N

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Description générale

Artemisinin is extracted from sweet wormwood (Artemisia annua).[1] It has anticancer,[1] antiprotozoal and antiviral activities.[2] Artemisinin is associated with brainstem encephalopathy.[3]

Application

Artemisinin has been used:
  • in drug susceptibility assays[4]
  • as a standard for its quantification from artemisinin from hairy roots[5]
  • to check cell viability using 3-(4, 5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay[6]
  • as an antimalarial agent to investigate the role of autophagy-related (ATG) genes throughout the P. falciparum asexual and sexual blood stages[7]

Actions biochimiques/physiologiques

Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Les clients ont également consulté

Stimulation of artemisinin synthesis by combined cerebroside and nitric oxide elicitation in Artemisia annua hairy roots
Wang JW, et al.
Applied Microbiology and Biotechnology, 85(2), 285-292 (2009)
Pierre-Eric Campos et al.
Marine drugs, 17(3) (2019-03-17)
Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F (1), 6-bromo-8,1'-dihydro-isoplysin A (2) and 5,6-dibromo-8,1'-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the
Artemether resistance in vitro is linked to mutations in PfATP6 that also interact with mutations in PfMDR1 in travellers returning with Plasmodium falciparum infections
Pillai DR, et al.
Malaria Journal, 11(1), 131-131 (2012)
Jürg Utzinger et al.
Current opinion in investigational drugs (London, England : 2000), 8(2), 105-116 (2007-03-03)
Schistosomiasis is a significant health issue caused by a blood fluke that affects more than 200 million individuals worldwide, over half of whom suffer from disease-associated symptoms. In areas of high burden, disease is mainly managed by controlling morbidity with
Rita Piedade et al.
Expert opinion on drug metabolism & toxicology, 7(10), 1185-1200 (2011-09-09)
Plasmodium falciparum malaria is one of the world's most lethal infectious diseases, commanding millions of drug administrations per year. The pharmacogenetics of these drugs is poorly known, although its application can be pivotal for the optimized management of this disease.

Questions

1–6 of 6 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. At what temperature do we store artemisinin

    1 answer
    1. This product is to be stored in room temperature.

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  4. Is there any expiry of this compound?

    1 answer
    1. This product is not assigned an expiration date or recommended retest date. Products with no expiration date or recommended retest date should be routinely inspected by customers to ensure they perform as expected. These products are also subject to a one year warranty from the date of shipment. For more information you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/life-science/quality-and-regulatory-management/quality-services.

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  5. In what solvents is Product 361593, Artemisinin, soluble?

    1 answer
    1. According to the chemicals encyclopedia published by the Royal Society of Chemistry, artemisinin is expected to be soluble in most aprotic solvents and slightly soluble in oil. Sigma-Aldrich tests the solubility of this product in chloroform at 25 mg/mL. Our quality control is also able to prepare a 0.5% solution in methanol in order to measure the optical rotation.

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  6. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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