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20069-09-4

20069-09-4 structure
20069-09-4 structure
  • Name: Piplartine
  • Chemical Name: Piperlongumine
  • CAS Number: 20069-09-4
  • Molecular Formula: C17H19NO5
  • Molecular Weight: 317.336
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-08-13 20:22:27
  • Modify Date: 2025-08-27 00:42:37
  • 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].
Name Piperlongumine
Synonyms Piperlongumine
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
(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
2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
Description 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
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
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 white to beige
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.581
Storage condition 2-8°C
Water Solubility DMSO: ≥5mg/mL at warmed to 60°C
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS UU7785850
HS Code 2933399090
6052-73-9 structure

6052-73-9

89652-63-1 structure

89652-63-1

~42%

20069-09-4 structure

20069-09-4

Literature: Boll, Per M.; Hansen, Jesper; Simonsen, Ole; Thorup, Niels Tetrahedron, 1984 , vol. 40, # 1 p. 171 - 176
21651-12-7 structure

21651-12-7

~%

20069-09-4 structure

20069-09-4

Literature: Tetrahedron, , vol. 40, # 1 p. 171 - 176
86-81-7 structure

86-81-7

~%

20069-09-4 structure

20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
1878-29-1 structure

1878-29-1

~%

20069-09-4 structure

20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
20329-98-0 structure

20329-98-0

~%

20069-09-4 structure

20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
1415686-28-0 structure

1415686-28-0

~%

20069-09-4 structure

20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
HS Code 2933399090
Summary 2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
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