| Identification | Back Directory | [Name]
PIPERLONGUMINE | [CAS]
20069-09-4 | [Synonyms]
ong
umine
PPLGM
PiperL
ongumine
Piplartin
acryloyl)
PIPLARTINE
PIPERLONGUMIN
PIPERLONGUMINE
Piperlangamine
PIPERLONGUMINE(P)
Piplartine powder
-5,6-dihydropyridin-2(1H)
Piperlongumine - Piplartine
-1-(3-(3,4,5-Trimethoxyphenyl)
piperlongumine from long pepper
Piperlongumine - CAS 20069-09-4 - Calbiochem
5,6-Dihydro-1-(3,4,5-triMethoxycinnaMoyl)-2(1H)-pyridone
(E)-1-(3-(3,4,5-TRIMETHOXYPHENYL)ACRYLOYL)PIPERIDIN-2-ONE
5,6-dihydro-1-[1-oxo-3-(3,4,5-triMethoxyphenyl)-allyl]-2(1H)-pyridinone
(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]pyridin-2(1H)-one
5,6-DIHYDRO-1-[1-OXO-3-3,4,5-TRIMETHOXYPHENYL-TRANS-2-PROPENYL]-21H-PYRIDINONE
(E)-5,6-Dihydro-1-[1-oxo-3-(3,4,5-triMethoxyphenyl)-2-propenyl]-2(1H)-pyridinone
5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-triMethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone
2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]- | [Molecular Formula]
C17H19NO5 | [MDL Number]
MFCD00075706 | [MOL File]
20069-09-4.mol | [Molecular Weight]
317.34 |
| Chemical Properties | Back Directory | [Melting point ]
124°C | [Boiling point ]
475.6±45.0 °C(Predicted) | [density ]
1.223±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥5mg/mL at warmed to 60°C | [form ]
powder | [pka]
-1.88±0.20(Predicted) | [color ]
white to beige | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. | [LogP]
2.340 (est) |
| Hazard Information | Back Directory | [Description]
A piperidinone alkaloid present in Piper longum, the structure has been shown
to be N-(3:4:5-trimethoxycinnamoyl)-Lls-piperidin-2-one. In the plant, the base
occurs mainly in the roots. | [Uses]
anti-asthma, antibronchitis | [Uses]
Piperlongumine (PL), a new alkaloid abundantly present in Piper longum fruits strongly inhibited platelet cell aggregation. It may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed. | [Definition]
ChEBI: Piplartine is a member of cinnamamides and a dicarboximide. | [General Description]
Piperlongumine is an alkaloid, which is extracted from Piper longum Linn. It exhibits anti-atherosclerotic, anxiolytic, antidiabetic, antidepressant, antibacterial, anti-platelet, aggregation, anxiolytic and anti-inflammatory properties. Piperlongumine prevents the production of tumor necrosis factor-α and interleukin-6. It blocks the activation of nuclear factor-κB (NF-κB) against proinflammatory responses. Piperlongumine inhibits plaque formation and inhibits vascular smooth muscle cell migration. It is used to treat cough, respiratory infections and stomach-ache. | [Biochem/physiol Actions]
Piperlongumine selectively kills cancer cells regardless of p53 status without harming normal cells. It binds to and inihbits proteins known to regulate oxidative stress, in particular, Glutathione S-transferase pi 1 (GSTP1). It increases the level of reactive oxygen species (ROS) and apoptotic cell death in cancer cells with little effect on either rapidly or slowly dividing primary normal cells. Piperlongumine showed significant antitumour effects in a variety of mouse tumour models and inhibited growth of spontaneously formed malignant breast tumours and their associated metastases. | [target]
P450 (e.g. CYP17) | Antifection | [References]
Chatterjee, Dutta., Tetrahedron, 23, 1769 (1967) |
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