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361593

Sigma-Aldrich

Artemisinin

98%

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Synonym(s):
Arteannuin, Qinghaosu
Empirical Formula (Hill Notation):
C15H22O5
CAS Number:
Molecular Weight:
282.33
MDL number:
PubChem Substance ID:
NACRES:
NA.79

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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This Item
PHL89484104274769532
Artemisinin 98%

Sigma-Aldrich

361593

Artemisinin

Artemisinin phyproof® Reference Substance

PHL89484

Artemisinin

Artemisinin United States Pharmacopeia (USP) Reference Standard

USP

1042747

Artemisinin

Artemisinin analytical standard

Supelco

69532

Artemisinin

form

solid

form

crystals

form

-

form

-

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

pharmaceutical (small molecule)

application(s)

food and beverages

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

100

optical activity

[α]20/D +76°, c = 0.5 in methanol

optical activity

-

optical activity

-

optical activity

[α]/D +75.0±3°, c = 0.5 in methanol

mp

156-157 °C (lit.)

mp

156-157 °C (lit.)

mp

156-157 °C (lit.)

mp

156-157 °C (lit.)

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

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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
Frédéric Ariey et al.
Nature, 505(7481), 50-55 (2013-12-20)
Plasmodium falciparum resistance to artemisinin derivatives in southeast Asia threatens malaria control and elimination activities worldwide. To monitor the spread of artemisinin resistance, a molecular marker is urgently needed. Here, using whole-genome sequencing of an artemisinin-resistant parasite line from Africa
Artemisinins: their growing importance in medicine
Krishna S, et al.
Trends in Pharmacological Sciences, 29(10), 520-527 (2008)
Antiprotozoal agents
Croft SL and Seifert K
Antibiotics and Chemotherapy, 29(10), 406-426 (2011)
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

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