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P0667

Sigma-Aldrich

Parthenolide

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C15H20O3
CAS Number:
20554-84-1
Molecular Weight:
248.32
MDL number:
MFCD00134592
UNSPSC Code:
12352200
PubChem Substance ID:
24278621
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

mp

115-116 °C (lit.)

storage temp.

2-8°C

SMILES string

C/C(CC[C@]12[H])=C/CC[C@]3(C)[C@H](O3)[C@]1(OC(C2=C)=O)[H]

InChI

1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13+,15+/m0/s1

InChI key

KTEXNACQROZXEV-ZRPLFPEYSA-N

Gene Information

human ... ELA2(1991) , IKBKG(8517) , NFKB1(4790) , NKAP(79576) , NKRF(55922)

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Application

Parthenolide has been used:
  • in the crystallization with vasohibin 1 (VASH1) to study tubulin detyrosination inhibition
  • as an inhibitor of nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) and signal transduction and activation of transcription (STAT) inhibitor to study its effects on the cytoadhesion of CD36-binding Plasmodium falciparum-infected erythrocytes (IECD36)
  • as a lipophilic agent to study its effects on the production of interleukin?13 and interferon?γ by peripheral blood-derived CD8+ T cells

Biochem/physiol Actions

Parthenolide is a sesquiterpene lactone present abundantly in the leaves and flowers of Tanacetum parthenium. It exhibits anti-cancer properties for the treatment of invasive cancers. Parthenolide exhibits therapeutic effects against inflammation and migraine. It plays a role in signal transduction and activation of transcription (STAT)-inhibition-mediated transcriptional repression of pro-apoptotic genes.
Anti-inflammatory agent that inhibits NF-κB activation.

Other Notes

Sesquiterpene lactone found in feverfew (Tanacetum parthenium) and other plants.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280 - P302 + P352

Hazard Classifications

Skin Sens. 1

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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Shanshan Pei et al.
The Journal of biological chemistry, 288(47), 33542-33558 (2013-10-04)
The development of strategies to eradicate primary human acute myelogenous leukemia (AML) cells is a major challenge to the leukemia research field. In particular, primitive leukemia cells, often termed leukemia stem cells, are typically refractory to many forms of therapy.
P A Spagnuolo et al.
Leukemia, 27(6), 1236-1244 (2013-01-16)
Parthenolide is selectively toxic to leukemia cells; however, it also activates cell protective responses that may limit its clinical application. Therefore, we sought to identify agents that synergistically enhance parthenolide's cytotoxicity. Using a high-throughput combination drug screen, we identified the
Eri Takai et al.
Fertility and sterility, 100(4), 1170-1178 (2013-07-24)
To evaluate the effects of parthenolide on human endometriotic cells and murine endometriotic lesions. Experimental study. University hospital and laboratory of animal science. Twenty women with ovarian endometrioma and 30 mice. Ectopic endometrial tissue from the endometrioma was collected. Human
Wieslaw Kozak et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 290(4), R871-R880 (2005-11-19)
Bacterial DNA containing unmethylated cytosine-phosphate-guanosine motif (CpG-DNA) has been identified as a pathogen-associated molecular pattern, which is recognized by Toll-like receptors and activates immune cells to produce cytokines. The aim of the study was to characterize the ability of CpG-DNA
Maria Regina Orofino Kreuger et al.
Anti-cancer drugs, 23(9), 883-896 (2012-07-17)
Sesquiterpene lactones (SLs) constitute a large and diverse group of biologically active plant compounds that possess anti-inflammatory and antitumor activity. The subclass germacranolides is one of the major groups of SLs. It includes parthenolide, a highly cytotoxic SL that is
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