Piperlongumine

Base Information

• Chemical Name: Piperlongumine
• CAS No.: 20069-09-4
• Molecular Formula: C17H19NO5
• Molecular Weight: 317.342
• Hs Code.: 2933399090
• European Community (EC) Number: 812-597-2
• UNII: SGD66V4SVJ
• DSSTox Substance ID: DTXSID801029762
• Nikkaji Number: J1.741.941B,J14.252B
• Wikipedia: Piperlongumine
• Wikidata: Q7197361
• Metabolomics Workbench ID: 44337
• ChEMBL ID: CHEMBL465843
• Mol file: 20069-09-4.mol

Synonyms:Piperlongumine;piperlonguminine

Chemical Property of Piperlongumine

Chemical Property:

• Melting Point: 124oC
• Boiling Point: 475.6°Cat760mmHg
• PKA: -1.88±0.20(Predicted)
• Flash Point: 241.4°C
• PSA: 65.07000
• Density: 1.223g/cm³
• LogP: 1.97860
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥5mg/mL at warmed to 60°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 317.12632271
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

98%,99%, ^*data from raw suppliers

Piperlongumine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
• 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: Piperlongumine 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. 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. anti-asthma, antibronchitis

Technology Process of Piperlongumine

There total 20 articles about Piperlongumine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

(E)-3-(phenylselanyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)piperidin-2-one → piperlongumine (20069-09-4)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃; for 0.75h;

DOI:10.1016/j.bmcl.2014.10.054

Reference yield: 51.0%

diethyl 2-oxo-2-(2-oxo-5,6-dihydropyridin-1(2H)-yl)ethylphosphonate + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → piperlongumine (20069-09-4)

Guidance literature:

diethyl 2-oxo-2-(2-oxo-5,6-dihydropyridin-1(2H)-yl)ethylphosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

3,4,5-trimethoxy-benzaldehyde; In tetrahydrofuran; at 0 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c6ob01160h

Reference yield: 43.0%

5,6-dihydro-2(1H)-pyridinone (6052-73-9) + (E)-3-(3,4,5-trimethoxyphenyl)acrylic anhydride (89652-63-1) → piperlongumine (20069-09-4)

Guidance literature:

In pyridine; toluene; at 45 ℃; for 168h;

DOI:10.1016/0040-4020(84)85116-9

upstream raw materials:

5,6-dihydro-2(1H)-pyridinone

(E)-3-(3,4,5-trimethoxyphenyl)acrylic anhydride

(E)-2,4-pentadienoic acid

3,4,5-trimethoxy-benzaldehyde

Downstream raw materials:

1-(3-(3,4,5-trimethoxyphenyl)propanoyl)piperidin-2-one

[-(3-(5-methoxy-1H-indol-3-yl)-3-(3,4,5-trimethoxyphenyl)propanoyl)-5,6-dihydropyridin-2(1H)-one]

(E)-3-(hydroxy(2-nitrophenyl)methyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate

Refernces

• 1、 Li, Li,Zhao, Yue,Cao, Ran,Li, Lin,Cai, Gaihong,Li, Jiaojiao,Qi, Xiangbing,Chen, She,Zhang, Zhiyuan. "Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer". . p. 4407 - 4410. Retrieved 2019/04/26.
• 2、 -. "Pipelongumine and its derivatives and producing method thereof". . . Retrieved 2017/01/05.