Basic information
- CAS
20069-09-4- Standard SMILES
COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(OC)c1OC- InChIKey
VABYUUZNAVQNPG-BQYQJAHWSA-N- Molecular formula
- C17H19NO5
- Average molar mass
- 317.34 g/mol
- Monoisotopic mass
- 317.12632271
Overview
Piplartine is a member of cinnamamides and a dicarboximide.
Names & identifiers
- Preferred name
- Piperlongumine
- IUPAC
- 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
- English name
- PIPERLONGUMINE
- Molecular formula
- C17H19NO5
- Molecular weight
- 317.34
Names & synonyms
PiperlonguminePiplartine20069-09-4SGD66V4SVJ1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-1-((E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl)-2,3-dihydropyridin-6-oneRefChem:455155,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-2(1H)pyridinone(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-oneMFCD000757062(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
Show more names
ongPPLGMuminePiperLongumineacryloyl)PIPERLONGUMINPiperlorgumia
1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-oneCHEBI:8241ST079382BRD2293PiplartinBRD-2293(E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-onePiplartine; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 65.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 473
Experimental & physicochemical properties
Melting Point124 °C
Physical DescriptionSolid
Collision Cross Section
174.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
176.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 124 °C · 124°C
- Boiling point
- 475.6 · 475.6±45.0 °C(Predicted)
- Density
- 1.223 · 1.223±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · DMSO: ≥5mg/mL at warmed to 60°C
- pka
- -1.88 · -1.88±0.20(Predicted)
- form
- powder
- color
- white to beige
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)
Safety data
- wgk
- 3
- rtecs
- UU7785850
- hs_code
- 2932209090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H320-H335
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionA 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.
UsesPiperlongumine 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.
Usesanti-asthma, antibronchitis
UsesPiperlongumine (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.
General DescriptionPiperlongumine 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.
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
Related reactions
3 records
Compound notes
Loading…