Piplartine

Modify Date: 2025-08-27 00:42:37

Piplartine Structure
Piplartine structure
 Common Name Piplartine
CAS Number 20069-09-4 Molecular Weight 317.336
Density 1.2±0.1 g/cm3 Boiling Point 475.6±45.0 °C at 760 mmHg
Molecular Formula C17H19NO5 Melting Point 124ºC
MSDS Chinese USA Flash Point 241.4±28.7 °C

 Use of Piplartine


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].

 Names

Name Piperlongumine
Synonym More Synonyms

 Piplartine Biological Activity

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

 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
Storage condition 2-8°C
Water Solubility DMSO: ≥5mg/mL at warmed to 60°C

 Safety Information

RIDADR NONH for all modes of transport
WGK Germany 3
RTECS UU7785850
HS Code 2933399090

 Synthetic Route

5,6-Dihydro-2(1H)-pyridinone structure

5,6-Dihydro-2(1...

CAS#:6052-73-9

N/A structure

N/A

CAS#:89652-63-1

~42%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: Boll, Per M.; Hansen, Jesper; Simonsen, Ole; Thorup, Niels Tetrahedron, 1984 , vol. 40, # 1 p. 171 - 176
trans-2,4-Pentadienoicacid structure

trans-2,4-Penta...

CAS#:21651-12-7

~%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: Tetrahedron, , vol. 40, # 1 p. 171 - 176
3,4,5-Trimethoxybenzaldehyde structure

3,4,5-Trimethox...

CAS#:86-81-7

~%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
Ethyl (2E)-3-(3,4,5-trimethoxyphenyl)acrylate structure

Ethyl (2E)-3-(3...

CAS#:1878-29-1

~%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
3,4,5-Trimethoxy-trans-cinnamic acid structure

3,4,5-Trimethox...

CAS#:20329-98-0

~%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361
N-(but-3-en-1-yl)acrylamide structure

N-(but-3-en-1-y...

CAS#:1415686-28-0

~%

Piplartine Structure

Piplartine

CAS#:20069-09-4

Literature: European Journal of Medicinal Chemistry, , vol. 57, p. 344 - 361

 Customs

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%

 Articles4

More Articles
Serotonergic signalling suppresses ataxin 3 aggregation and neurotoxicity in animal models of Machado-Joseph disease.

Brain 138 , 3221-37, (2015)

Polyglutamine diseases are a class of dominantly inherited neurodegenerative disorders for which there is no effective treatment. Here we provide evidence that activation of serotonergic signalling is...

Piperlongumine induces apoptotic and autophagic death of the primary myeloid leukemia cells from patients via activation of ROS-p38/JNK pathways.

Acta Pharmacol. Sin. 36(3) , 362-74, (2015)

To investigate the effects of piperlongumine (PL), an anticancer alkaloid from long pepper plants, on the primary myeloid leukemia cells from patients and the mechanisms of action.Human BM samples wer...

Piperlongumine for Enhancing Oral Bioavailability and Cytotoxicity of Docetaxel in Triple-Negative Breast Cancer.

J. Pharm. Sci. 104 , 4417-26, (2016)

Very low oral bioavailability due to extensive pre-systemic metabolism and P-gp efflux has constrained the oral metronomic chemotherapy of docetaxel (DTX). There is tremendous need of compounds facili...

 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
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