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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

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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).[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]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000383864
0000383864
MKCW0906
MKCS1414
MKCP2657

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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)
C J Paddon et al.
Nature, 496(7446), 528-532 (2013-04-12)
In 2010 there were more than 200 million cases of malaria, and at least 655,000 deaths. The World Health Organization has recommended artemisinin-based combination therapies (ACTs) for the treatment of uncomplicated malaria caused by the parasite Plasmodium falciparum. Artemisinin is a
Artemisinins: their growing importance in medicine
Krishna S, et al.
Trends in Pharmacological Sciences, 29(10), 520-527 (2008)
Deciphering genetic regulation of CD14 by SP1 through characterization of peripheral blood mononuclear transcriptome of P. faiciparum and P. vivax infected malaria patients
Chakraborty B, et al.
EBioMedicine, 37, 442-452 (2018)
View All Related Papers

Questions

1–4 of 4 Questions  

  1. At what temperature do we store artemisinin

    1 answer

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

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  2. 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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  3. 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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  4. 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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