| Identification | Back Directory | [Name]
Parthenolide | [CAS]
20554-84-1 | [Synonyms]
PTL
Nsc157035
Aids007764
Parthelide
Aids-007764
Parthenolide
PartheNAlide
Parthenolides
Parthenolide(PTL)
Parthenolide (25 mg)
Parthenolide ((-)-Parthenolide)
PARTHENOLIDE, TANACETUM PARTHENIUM
Parthenolide from Chrysanthenum parthenium
Oxireno(9,10)cyclodeca(1,2-B)furan-9(1ah)-o
Parthenolide, froM ChrysantheMuM MorifoliuM
Parthenolide, 98%, from Chrysanthemum morifolium
4,5α-Epoxy-6β-hydroxygermacra-1(10),11(13)-dien-12-oic acid γ-lactone
4,5-alpha-epoxy-6-beta-hydroxy-11(13)-dien-12-oicacigamma-germacra-1(10
4,5-alpha-epoxy-6-beta-hydroxygermacra-1(10),11(13)-dien-12-oicacidgamma-la
4,5alpha-epoxy-6beta-hydroxy-germacra-1(10),11(13)-dien-12-oic acid gamma-lactone
Germacra-1(10),11(13)-dien-12-oic acid, 4,5-alpha-epoxy-6-beta-hydroxy-, gamma-lactone
(1aR,4E,7aS,10aS,10bS)-2,3,6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Oxireno9,10cyclodeca1,2-bfuran-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7aS,10aS,10bR)-
Oxireno[9,10]cyclodeca[1,2-B]furan-9(1ah)-one, 2,3,6,7,7A,8,10A,10B-octahydro-1A,5-dimethyl-8-methylene-, (1ar,4E,7as,10as,10bs)-
(3aS,9aR,10aS,10bS,E)-6,9a-dimethyl-3-methylene-3a,4,5,8,9,9a,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-2(3H)-one
[1AR-(1AR*,4E,7AS*,10AS*-10BR*)]-2,3-6,7,7A,8,10A,10B-OCTAHYDRO-1A,5-DIMETHYL-8-METHYLENEOXIRENO[9,10]CYCLODECA[1,2-B]FURAN-9(1AH)-ONE
[1aR-(1aR*,4E,7aS*,10aS*,-10bR*)]-2,3-6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C15H20O3 | [MDL Number]
MFCD00134592 | [MOL File]
20554-84-1.mol | [Molecular Weight]
248.32 |
| Chemical Properties | Back Directory | [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. ]
2-8°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 | [Contact allergens]
Parthenolide is a sesquiterpene lactone found Asteraceae-
Compositae such as feverfew (Tanacetum parthenium
Schultz-Bip.) or congress grass (Parthenium hysterophorus
L.). | [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 DataBase Reference]
20554-84-1 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Antiinflammatory;MAP kinase inhibitor | [Definition]
ChEBI: A sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium). | [Uses]
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-κBand 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. | [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 . | [Description]
Parthenolide is an allergen in feverfew (Tanacetum
parthenarium). | [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 | [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. | [storage]
Store at -20°C | [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 |
|
|