PIPERLONGUMINE

For Research Use Only.
Category
Alkaloids
Cat.No.
NP0012
CAS
20069-09-4
Product Name
PIPERLONGUMINE
Structure

Product Details

Description
Piperlongumine, also known as Piplartine , is a biologically active alkaloid/amide from peppers, as from long pepper (Piper longum L. - Piperaceae). Long pepper is one of the most widely used in Ayurvedic medicine, which is used to treat many diseases, including tumors. The reported pharmacological activities of piplartine include cytotoxic, genotoxic, antitumor, antiangiogenic, antimetastatic, antiplatelet aggregation, antinociceptive, anxiolytic, antidepressant, anti-atherosclerotic, antidiabetic, antibacterial, antifungal, leishmanicidal, trypanocidal, and schistosomicidal activities. Among the multiple pharmacological effects of piplartine, its anticancer property is the most promising. Therefore, the preclinical anticancer potential of piplartine has been extensively investigated, which recently resulted in one patent. This compound is selectively cytotoxic against cancer cells by induction of oxidative stress, induces genotoxicity, as an alternative strategy to killing tumor cells, has excellent oral bioavailability in mice, inhibits tumor growth in mice, and presents only weak systemic toxicity.
Synonyms
Piplartine; 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone; (E)-5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone; Piplartin; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one; NSC-794671
IUPAC Name
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Molecular Weight
317.34
Molecular Formula
C17H19NO5
Canonical SMILES
COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
InChI
InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChIKey
VABYUUZNAVQNPG-BQYQJAHWSA-N
Boiling Point
475.6±45.0°C (Predicted)
Melting Point
122-124°C
Flash Point
241.4°C
Purity
≥98%
Density
1.223±0.06 g/cm3 (Predicted)
Solubility
Soluble in Chloroform (Slightly), Methanol (Slightly)
Appearance
Off-white to Yellow Solid
Storage
Store at -20°C
Color
Pale Yellow to Yellow
Form
Solid
MDL
MFCD00075706
NACRES
NA.77
pKa
-1.88±0.20(Predicted)
Quality Level
100
RTECS
UU7785850
Stability
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
Uses
Piperlongumine has been used to study the regulation of protein regulator of cytokinesis 1 (PRC1) expression. It has also been used to investigate its anti-tumor effects on human melanoma cells in vitro.
WGK Germany
3
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