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HomeProduct name listParthenolide

Parthenolide

Synonym(s):Parthenolide, Tanacetum parthenium - CAS 20554-84-1 - Calbiochem

  • CAS NO.:20554-84-1
  • Empirical Formula: C15H20O3
  • Molecular Weight: 248.32
  • MDL number: MFCD00134592
  • EINECS: 692-532-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-04 15:29:52
Parthenolide Structural

What is Parthenolide?

Description

Parthenolide is an allergen in feverfew (Tanacetum parthenarium).

Chemical properties

White solid

The Uses of Parthenolide

Parthenolide is a sesquiterpene lactone from the plant feverfew (T. parthenium). It inhibits the growth of the promastigote form of L. amazonensis (IC50 = 3.6 μg/ml). Parthenolide also induces apoptosis in cancer cells, at least in part by inhibiting NF-κB- and STAT-mediated anti-apoptotic gene transcription. This compound has also been shown to block inflammation by inhibiting signaling through NF-κB. Inhibition of NF-κB by parthenolide can be achieved by direct binding of the pattern recognition receptor NOD2 by parthenolide.

The Uses of Parthenolide

Antiinflammatory;MAP kinase inhibitor

The Uses of Parthenolide

Parthenolide is an anti-inflammatory agent used in the treatment of ischemic injury. Also acts as an anti-tumor and anti0leukemia agent targetting acute myeloid leukemia.

Background

Parthenolide has been used in trials studying the diagnostic of Allergic Contact Dermatitis.

What are the applications of Application

Parthenolide is an inhibitor specifically inhibits HDAC1 without affecting other class I/II HDACs

Definition

ChEBI: A sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium).

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

The active principle of feverfew (Chrysanthemum parthenium), widely used as a herbal remedy for arthritis and migraine and as a febrifuge. Parthenolide is antisecretory, anti-inflammatory, spasmolytic and inhibits the release of 5-HT from blood platelets. Also inhibits generation of leukotriene B 4 and thromboxane B 2 .

Contact allergens

Parthenolide is a sesquiterpene lactone found Asteraceae- Compositae such as feverfew (Tanacetum parthenium Schultz-Bip.) or congress grass (Parthenium hysterophorus L.).

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.

Metabolism

Not Available

References

1) Kwok et al. (2001), The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IkappaB kinase; Chem. Biol., 8 759 2) Hwang et al. (1996), Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sequiterpene lactones in macrophages correlates with the inhibition of MAP kinases; Biochem. Biophys. Res. Commun., 226 810 3) Barsby et al. (1992), Feverfew extracts and parthenolide irreversibly inhibit vascular responses of the rabbit aorta; J. Pharm. Pharmacol., 44 737 4) Sumner et al. (1992), Inhibition of 5-lipoxygenase and cyclo-oxygenase in leukocytes by feverfew. Involvement of sesquiterpene lactones and other components; Biochem. Pharmacol., 43 2313 5) Groenewegen et al. (1990), A comparison of the effects of an extract of feverfew and parthenolide, a component of feverfew, on human platelet activity in-vitro; J. Pharm. Pharmacol., 42 553

Properties of Parthenolide

Melting point: 115-116 °C (lit.)
alpha  D20 -81.4° (c = 1.04 in chloroform); D22 -71.4° (c = 0.220 in CH2Cl2)
Boiling point: 394.1±42.0 °C(Predicted)
Density  1.13±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 20 mg/ml)
form  White solid
color  White
Merck  14,7048
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI 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
CAS DataBase Reference 20554-84-1

Safety information for Parthenolide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H317:Sensitisation, Skin
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for Parthenolide

InChIKey KTEXNACQROZXEV-PVLRGYAZSA-N
SMILES O1C(=O)C(=C)[C@]2([H])CCC(C)=CCC[C@@]3(C)O[C@]3([H])[C@@]12[H] |t:10|

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