ChemicalBook > CAS DataBase List > Parthenolide

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
More
Less

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
More
Less

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
More
Less

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.

More
Less

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
More
Less

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

More
Less

Parthenolide Suppliers

Nanjing Spring & Autumn Biological Engineering Co., Ltd.
Tel
025-84430028 13815430202
Email
sale02@cqherb.com
Country
China
ProdList
281
Advantage
59
Shaanxi xintianyu Biotechnology Co., Ltd.
Tel
17749282610
Fax
029-32562222
Email
3002817800@qq.com
Country
China
ProdList
981
Advantage
58
Shaanxi xintianyu Biotechnology Co., Ltd.
Tel
029-32565555 17791023282
Email
943175747@qq.com
Country
China
ProdList
416
Advantage
58
Chengdu Push Bio-Technology Co., Ltd.
Tel
028-85370565-229 18080489829
Email
3004654993@qq.com
Country
China
ProdList
8861
Advantage
60
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8418
Advantage
55
More
Less

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:


  • 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