Parthenolide

Product Name: Parthenolide
CAS No.: 20554-84-1
Chemical Name: Parthenolide
Synonyms: PTL;Nsc157035;Aids007764;Parthelide;Aids-007764;Parthenolide;PartheNAlide;Parthenolides;parthenolider;Parthenolide>
CBNumber: CB0446848
Molecular Formula: C15H20O3
Formula Weight: 248.32
MOL File: 20554-84-1.mol

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Parthenolide Property

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
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

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Safety

Hazard Codes: Xi,C,F
Risk Statements: 11-34
Safety Statements: 22-24/25-45-36/37/39-26-16
WGK Germany: 3
RTECS: LY4220000
HS Code: 29322090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL89255
Product name: Parthenolide
Purity: phyproof? Reference Substance
Packaging: 20MG
Price: $288
Updated: 2024/03/01

Sigma-Aldrich

Product number: 512732
Product name: Parthenolide
Packaging: 50mg
Price: $99.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1500400
Product name: Parthenolide
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 25mg
Price: $240
Updated: 2024/03/01

TCI Chemical

Product number: P1982
Product name: Parthenolide
Purity: >97.0%(HPLC)
Packaging: 25mg
Price: $87
Updated: 2024/03/01

TCI Chemical

Product number: P1982
Product name: Parthenolide
Purity: >97.0%(HPLC)
Packaging: 100mg
Price: $258
Updated: 2024/03/01

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Parthenolide Chemical Properties,Usage,Production

Description

(-)-Parthenolide (PTL) is a natural sesquiterpene lactone produced as a secondary metabolite by plants of the Asteraceae/ Compositae (daisies) and Magnoliaceae family (magnolias). It was first isolated from feverfew (Tanacetum parthenium L. Schulz Bip. or synonymously Chrysanthemum parthenium L. Bernh.). The plant owes its name to its use as a long known natural remedy for alleviating fever, migraine, rheumatoid arthritis, stomach ache, toothache, and insect bites, among other ailments. After it was shown that parthenolide is the main biologically active ingredient of these plant(s)1b, many studies have described promising anti-inflammatory and anti-tumour properties of the natural product. Interestingly, it was shown that PTL was cytotoxic to tumor cells while almost not affecting healthy cells at similar concentrations. Moreover, it was reported to be one of the few small molecules that selectively target cancer stem cells, which are still difficult to treat and a suspected reason for tumour relapse[6].

Chemical Properties

White solid

Uses

Antiinflammatory;MAP kinase inhibitor

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-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.

Uses

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: Parthenolide is a sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium). It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a peripheral nervous system drug, an inhibitor and a drug allergen.

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 .

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.

Contact allergens

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

Mechanism of action

Parthenolide (PTL) is a potent NF-κB signaling inhibitor that exerts anti-inflammatory effects by inhibiting IκBα depletion, thereby inhibiting excessive NF-κB activation. It also inhibits the nuclear translocation of the p65 subunit and the DNA binding of the NF-κB complex to exert anti-tumor effects. In addition, it inhibits STAT and MAP kinase activity and induces sustained JNK activity and p53 activity by affecting MDM2 and HDAC1 levels, resulting in increased sensitivity of cancer cells to chemotherapy and radiotherapy. The most unique property is that it can induce cell death mainly in cancer cells while sparing healthy cells, and it also protects normal cells from UVB and oxidative stress.

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
6) Freund, Robert R. A. et al. “Advances in chemistry and bioactivity of parthenolide?.” Natural Product Reports 4 (2019): 541–565.

Parthenolide Preparation Products And Raw materials

Raw materials

Preparation Products

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Parthenolide Suppliers

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View Lastest Price from Parthenolide manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: Parthenolide 20554-84-1
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-27

Hebei Kingfiner Technology Development Co.Ltd

Product: Parthenolide 20554-84-1
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 50000kg
Release date: 2024-05-20

Henan Fengda Chemical Co., Ltd

Product: Parthenolide 20554-84-1
Price: US $10.00-2.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-28

20554-84-1, ParthenolideRelated Search:

D-(+)-Glucono-1,5-lactone Spironolactone Kauniolide Glycidyl methacrylate 2-BUTOXYETHYL ACRYLATE Glycidyl acrylate CITRONELLYL BUTYRATE 6-decenoic acid Allyl glycidyl ether Glycidyl butyrate METHYL TUBERATE 1,2-EPOXY-5-HEXENE (S)-(+)-Glycidyl butyrate 2-N-BUTOXYETHYL METHACRYLATE Tulipalin A Whiskey lactone FEVERFEW Parthenolide

Parthenolide, Tanacetum parthenium - CAS 20554-84-1 - Calbiochem

Factory Price Parthenolide 20554-84-1

Natural Plant Extracts Parthenolide 20554-84-1 High Purity HPLC>98%

Feverfew P.E Parthenlide

[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,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

4,5α-Epoxy-6β-hydroxygermacra-1(10),11(13)-dien-12-oic acid γ-lactone

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

Parthenolide

Parthenolide ((-)-Parthenolide)

PartheNAlide

Aids007764

Aids-007764

Nsc157035

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)-

Parthenolides

Parthelide

Parthenolide (25 mg)

Oxireno(9,10)cyclodeca(1,2-B)furan-9(1ah)-o

Parthenolide, froM ChrysantheMuM MorifoliuM

(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

PTL

Parthenolide(PTL)

[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

PARTHENOLIDE, TANACETUM PARTHENIUM

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

Parthenolide from Chrysanthenum parthenium

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)-

Parthenolide, 98%, from Chrysanthemum morifolium

Parthenolide&gt

(-)-Parthenolide

PARTHENOLIDE, DIMETHYLAMINOPARTHENOLIDE

parthenolider

Chrysanthemum lactone

Autophagy,inhibit,Parthenolide,Nuclear factor-kappaB,Mitochondrial Autophagy,NF-κB,Nuclear factor-κB,Apoptosis,Inhibitor,Mitophagy

(3aS,9aR,10aR,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

Parthenolide-RM

20554-84-1

10-21-7

20552-41-8

Anti-Proliferative Agents

Antitumor Agents

BioChemical

Cancer Research

inhibitor

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Natural Product

Sesqui-Terpenoids

Isoprenoid/terpenoidNeurotransmitters

Anti-Proliferative AgentsNutrition Research

Antitumor Agents

Biochemicals Found in Plants