Parthenolide

Bezeichnung:Parthenolide

CAS-Nr20554-84-1

Englisch Name:Parthenolide

CBNumberCB0446848

SummenformelC15H20O3

Molgewicht248.32

MOL-Datei20554-84-1.mol

Parthenolide physikalisch-chemischer Eigenschaften

Schmelzpunkt	115-116 °C (lit.)
alpha	D20 -81.4° (c = 1.04 in chloroform); D22 -71.4° (c = 0.220 in CH2Cl2)
Siedepunkt	394.1±42.0 °C(Predicted)
Dichte	1.13±0.1 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 20 mg/ml)
Aggregatzustand	White solid
Farbe	White
Merck	14,7048
Stabilität	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
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\|
LogP	2.424 (est)
CAS Datenbank	20554-84-1

Sicherheit

Kennzeichnung gefährlicher	Xi,C,F
R-Sätze:	11-34
S-Sätze:	22-24/25-45-36/37/39-26-16
WGK Germany	3
RTECS-Nr.	LY4220000
HS Code	29322090

Gefahreninformationscode (GHS)

Parthenolide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Beschreibung
Parthenolide is an allergen in feverfew (Tanacetum parthenarium).
Chemische Eigenschaften
White solid
Verwenden
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.
Verwenden
Antiinflammatory;MAP kinase inhibitor
Verwenden
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.
Definition
ChEBI: A sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium).
Allgemeine Beschreibung
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
Biologische Aktivität
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 .
Kontakt-Allergie
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.
Einzelnachweise
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

Parthenolide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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