CAS Number20069-09-4
SynonymsPiperlongumine; 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one; (E)-Piplartine; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone; piplartine; 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
Molecular FormulaC17H19NO5
Molecular Weight317.34
Purity≥97 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point475.6±45.0 °C at 760 mmHg
Melting Point124ºC
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 20069-09-4 |
| Catalog No. | 2A-9016899 |
| Chinese Name | 荜茇酰胺 |
| Synonyms | Piperlongumine; 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one; (E)-Piplartine; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone; piplartine; 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one |
| Molecular Formula | C17H19NO5 |
| Molecular Weight | 317.34 |
| Purity | ≥97 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 475.6±45.0 °C at 760 mmHg |
| Melting Point | 124ºC |
| Appearance | solid |
| Water Solubility | DMSO: ≥5mg/mL at warmed to 60°C |
| Storage Condition | 2-8°C |
| Application | Piperlongumine is an alkaloid obtained from Piper longum[1] and has anti-inflammatory, antibacterial, anti-angiogenic, antioxidant, anti-tumor and anti-diabetic activities[2]. In tumor cells, Piperlon |
| HTC | 2933399090 |
| UN(IATA) | NA |
| MDL Number | MFCD00075706 |
| SMILES | O=C1N(C(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O)CCC=C1 |
| 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+ |
| InChI Key | VABYUUZNAVQNPG-BQYQJAHWSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352100 |
| Hazard Symbols | Transport |
| MSDS | msds/16899_1_20069_09_4.pdf |
| Bioactivity | Piperlongumine is a natural alkaloid isolated from Piper longum Linn[1], possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities[2]. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines[1]. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2]. Related Catalog Signaling Pathways >> MAPK/ERK Pathway >> ERK Signaling Pathways >> Stem Cell/Wnt >> ERK Natural Products >> Alkaloid Research Areas >> Cancer Research Areas >> Cardiovascular Disease Research Areas >> Infection Target ERK1 ERK2 In Vitro Piplartine (5, 10, and 15 μM) significantly decreases cell proliferation of 786-O, SKBR3, Panc1, A549, and L3.6pL cancer cells after treatment for 24 and 48 hours, induces apoptosis and ROS in these cell lines at 5 and 10 μM after 3 or 9 h of treatment[1]. Piplartine (5 or 10 μM) induces cleaved PARP and downregulates Sp1, Sp3, Sp4, and Sp-regulated genes[1]. Piplartine (20 μM) decreases the viability of cardiac fibroblasts (CFs). Piplartine (0-10 μM) suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway[2]. In Vivo Piperlongumine (30 mg/kg/day, i.p. for 3 weeks) exhibits potent anti-tumor effect in athymic nude mice bearing L3.6pL cells without body weight loss[1]. References [1]. Karki K, et al. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors. [2]. 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 Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 475.6±45.0 °C at 760 mmHg Melting Point 124ºC Molecular Formula C17H19NO5 Molecular Weight 317.336 Flash Point 241.4±28.7 °C Exact Mass 317.126312 PSA 65.07000 LogP 2.34 Appearance of Characters white to beige Vapour Pressure 0.0±1.2 mmHg at 25°C Index of Refraction 1.581 InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N SMILES COc1cc(C=CC(=O)N2CCC=CC2=O)cc(OC)c1OC Storage condition 2-8°C Water Solubility DMSO: ≥5mg/mL at warmed to 60°C |
| Use of | Properties Name Piperlongumine Synonym More Synonyms Piplartine Biological Activity Related Catalog Signaling Pathways >> MAPK/ERK Pathway >> ERK Signaling Pathways >> Stem Cell/Wnt >> ERK Natural Products >> Alkaloid Research Areas >> Cancer Research Areas >> Cardiovascular Disease Research Areas >> Infection References [1]. Karki K, et al. Piperlongumine Induces Reactive Oxygen Species (ROS)-Dependent Downregulation of Specificity Protein Transcription Factors. [2]. 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 Chemical & Physical Properties Molecular Formula C17H19NO5 Exact Mass 317.126312 PSA 65.07000 Appearance of Characters white to beige Index of Refraction 1.581 InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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