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P0667

Sigma-Aldrich

Parthenolide

≥98% (HPLC)

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Empirical Formula (Hill Notation):
C15H20O3
CAS Number:
Molecular Weight:
248.32
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
566313598226662107
Parthenolide ≥98% (HPLC)

P0667

Parthenolide

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form

powder

form

powder

form

powder

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

mp

115-116 °C (lit.)

mp

-

mp

-

mp

-

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Akram Ghantous et al.
Drug discovery today, 18(17-18), 894-905 (2013-05-22)
Parthenolide (PTL), a sesquiterpene lactone (SL) originally purified from the shoots of feverfew (Tanacetum parthenium), has shown potent anticancer and anti-inflammatory activities. It is currently being tested in cancer clinical trials. Structure-activity relationship (SAR) studies of parthenolide revealed key chemical
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
Veera Reddy Konda et al.
Journal of inflammation (London, England), 6, 26-26 (2009-08-29)
Rho iso-alpha acids (RIAA) from hops have been shown to have anti-inflammatory properties. To understand the mechanisms, we evaluated the effect of RIAA in cell signaling pathways and inflammatory markers using various in vitro models. We also investigated their therapeutic
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

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