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361593

Sigma-Aldrich

Artemisinin

98%

Synonym(s):

Arteannuin, Qinghaosu

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About This Item

Empirical Formula (Hill Notation):
C15H22O5
CAS Number:
63968-64-9
Molecular Weight:
282.33
MDL number:
MFCD00081057
UNSPSC Code:
12352205
PubChem Substance ID:
57649481
NACRES:
NA.79

Quality Level

100

Assay

98%

form

solid

optical activity

[α]20/D +76°, c = 0.5 in methanol

mp

156-157 °C (lit.)

antibiotic activity spectrum

parasites
viruses

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Mode of action

enzyme | inhibits

SMILES string

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

InChI key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

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General description

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

Application

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

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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    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. 

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

    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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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)
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
Olivo Miotto et al.
Nature genetics, 45(6), 648-655 (2013-04-30)
We describe an analysis of genome variation in 825 P. falciparum samples from Asia and Africa that identifies an unusual pattern of parasite population structure at the epicenter of artemisinin resistance in western Cambodia. Within this relatively small geographic area
The multifunctional autophagy pathway in the human malaria parasite, Plasmodium falciparum
Cervantes S, et al.
Autophagy, 10(1), 80-92 (2014)
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