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20069-09-4,MFCD00075706
Catalog No.:AA002CU6

20069-09-4 | Piperlongumine

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
98%
in stock  
$7.00   $5.00
- +
5mg
98%
in stock  
$24.00   $17.00
- +
10mg
98%
in stock  
$36.00   $25.00
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25mg
≥98%
in stock  
$63.00   $44.00
- +
50mg
98%
in stock  
$94.00   $66.00
- +
100mg
97%
in stock  
$100.00   $70.00
- +
250mg
95%
in stock  
$220.00   $154.00
- +
1g
95%
in stock  
$544.00   $381.00
- +
5g
95%
in stock  
$1,607.00   $1,125.00
- +
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002CU6
Chemical Name:
Piperlongumine
CAS Number:
20069-09-4
Molecular Formula:
C17H19NO5
Molecular Weight:
317.3365
MDL Number:
MFCD00075706
SMILES:
COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(c1OC)OC
Properties
Properties
 
Form:
Solid  
MP:
124°C  
Solubility:
DMSO: ≥5mg/mL at warmed to 60°C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
473  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
5  
Rotatable Bond Count:
5  
XLogP3:
2.1  

Upstream Synthesis Route

[1]Phytochemistry(Elsevier),1985,vol.24,#11,p.2589-2592

[1]EuropeanJournalofMedicinalChemistry,2012,vol.57,p.344-361

[2]BioorganicandMedicinalChemistry,2018,vol.26,#14,p.3925-3938

[1]OrganicandBiomolecularChemistry,2016,vol.14,#31,p.7585-7593

[1]JournalofMedicinalChemistry,2015,vol.58,#13,p.5242-5255

[2]ChemMedChem,2014,vol.9,#12,p.2725-2743

[1]Tetrahedron,1984,vol.40,#1,p.171-176

Downstream Synthesis Route

[1]Phytochemistry,1985,vol.24,p.2589-2592

[2]RSCAdvances,2018,vol.8,p.21407-21413

20069-09-4   
1,1'-(1α,2α,3β,4β)-2,4-bis(3,4,5-tri-methoxyphenyl)cyclobutane-1,3-diyldicarbonyl}-bis5,6-dihydropyridin-2(1H)-one 
 
C34H38N2O10 

[1]Phytochemistry,1981,vol.20,p.345

[1]Tetrahedron,1984,vol.40,p.171-176

[1]Phytochemistry,1985,vol.24,p.2589-2592

[1]Phytochemistry,1985,vol.24,p.2589-2592

Literature

Title: Piperlongumine decreases cell proliferation and the expression of cell cycle-associated proteins by inhibiting Akt pathway in human lung cancer cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20180101

Title: Piperlongumine is a novel nuclear export inhibitor with potent anticancer activity.

Journal: Chemico-biological interactions 20150725

Title: Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling.

Journal: Biochemical and biophysical research communications 20121019

Title: A novel flow cytometric HTS assay reveals functional modulators of ATP binding cassette transporter ABCB6.

Journal: PloS one 20120101

Title: Simultaneous UFLC-ESI-MS/MS determination of piperine and piperlonguminine in rat plasma after oral administration of alkaloids from Piper longum L.: application to pharmacokinetic studies in rats.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20111001

Title: Selective killing of cancer cells by a small molecule targeting the stress response to ROS.

Journal: Nature 20110714

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Diferuloylmethane augments the cytotoxic effects of piplartine isolated from Piper chaba.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20090901

Title: Antihyperlipidemic compounds from the fruit of Piper longum L.

Journal: Phytotherapy research : PTR 20090801

Title: Inhibitory effect of piperlonguminine/ dihydropiperlonguminine on the production of amyloid beta and APP in SK-N-SH cells.

Journal: The Chinese journal of physiology 20090630

Title: Antiplatelet activities of newly synthesized derivatives of piperlongumine.

Journal: Phytotherapy research : PTR 20080901

Title: In vivo growth inhibition of sarcoma 180 by piperlonguminine, an alkaloid amide from the Piper species.

Journal: Journal of applied toxicology : JAT 20080701

Title: Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.

Journal: Bioorganic & medicinal chemistry letters 20080601

Title: Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase.

Journal: Archives of pharmacal research 20080601

Title: [Antiatherogenic effect of piperlonguminine on experimental atherosclerosis in rabbits].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080201

Title: Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist.

Journal: European journal of pharmacology 20070910

Title: Inhibition of beta-amyloid precursor protein gene in SK-N-SH cells by piperlonguminine/dihydropiperlonguminine components separated from Chinese herbal medicine Futokadsura stem.

Journal: The Chinese journal of physiology 20070831

Title: Inhibitory effect of ethanol extract of Piper longum L. on rabbit platelet aggregation through antagonizing thromboxane A2 receptor.

Journal: Biological & pharmaceutical bulletin 20070701

Title: Suppression of ochratoxin biosynthesis by naturally occurring alkaloids.

Journal: Food additives and contaminants 20070401

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression.

Journal: Pigment cell research 20060201

Title: Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells.

Journal: Planta medica 20041201

Title: Karki K, et al. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors.

Title: Wu X, e,t al. Piperlongumine inhibits angiotensin II-induced extracellular matrix expression in cardiac fibroblasts. J Cell Biochem. 2018 Dec;119(12):10358-10364

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