Piperlonguminine

Base Information

• Chemical Name: Piperlonguminine
• CAS No.: 5950-12-9
• Molecular Formula: C16H19 N O3
• Molecular Weight: 273.332
• Hs Code.: 2932999099
• NSC Number: 125178
• UNII: HN39MC8KIO
• DSSTox Substance ID: DTXSID401021742
• Nikkaji Number: J1.272.834D,J542.747I,J712.463E
• Wikipedia: Piperlonguminine
• Wikidata: Q15425267
• Pharos Ligand ID: UKR2SM5ZD65M
• Metabolomics Workbench ID: 44242
• ChEMBL ID: CHEMBL253973
• Mol file: 5950-12-9.mol

Synonyms:Piperlongumine;piperlonguminine

Chemical Property of Piperlonguminine

Chemical Property:

• Vapor Pressure: 2.94E-09mmHg at 25°C
• Boiling Point: 476.9°C at 760 mmHg
• Flash Point: 242.2°C
• PSA: 47.56000
• Density: 1.136g/cm³
• LogP: 3.14780
• Solubility.: ≤3mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 273.13649347
• Heavy Atom Count: 20
• Complexity: 376

Purity/Quality:

≥98% ^*data from raw suppliers

Piperlonguminine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CNC(=O)C=CC=CC1=CC2=C(C=C1)OCO2
• Isomeric SMILES: CC(C)CNC(=O)/C=C/C=C/C1=CC2=C(C=C1)OCO2
• Description: This amide alkaloid also occurs in the roots of Piper longum and yields colourless needles from EtOH. The ultraviolet spectrum exhibits absorption maxima at 245,256, 307 and 340 mil. The side chain is doubly unsaturated and on catalytic hydrogenation, the base furnishes the tetrahydro derivative, m.p. 66°C. Piperlonguminine is an alkaloid amide from species of the genus Piper, a plant used in traditional medicine that demonstrates antifungal, anticancer, antihyperlipidemic, and anti-inflammatory properties. Piperlonguminine (3-12.5 μM) has been shown to dose dependently decrease expression of amyloid precursor protein and amyloid-β peptide in human neuroblastoma cells, suggesting it may have implication in treating Alzheimer’s disease.

Technology Process of Piperlonguminine

There total 22 articles about Piperlonguminine 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: 93.0%

isobutylamine (78-81-9) + piperic acid (136-72-1) → piperlonguminine (5950-12-9)

Guidance literature:

piperic acid; With thionyl chloride; In dichloromethane; for 1h; Reflux;

isobutylamine; In dichloromethane; for 1h;

DOI:10.1016/j.bmc.2008.09.042

Reference yield: 86.0%

isobutylamine (78-81-9) + piperic acid chloride (4711-72-2) → piperlonguminine (5950-12-9)

Guidance literature:

With triethylamine; at 20 ℃; for 5h; Cooling with ice;

DOI:10.1248/cpb.c14-00874

Reference yield: 84.0%

2-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]-N-isobutylacetamide (736947-73-2) → piperlonguminine (5950-12-9)

Guidance literature:

With aluminum oxide; potassium hydroxide; dibromodifluoromethane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1139/v04-028

upstream raw materials:

(E)-5-Benzo[1,3]dioxol-5-yl-5-hydroxy-pent-2-enoic acid isobutyl-amide

isobutylamine

piperic acid

piperic acid chloride

Refernces

• 1、 Takao, Koichi,Miyashiro, Takaki,Sugita, Yoshiaki. "Synthesis and biological evaluation of piperic acid amides as free radical scavengers and αglucosidase inhibitors". . p. 326 - 333. Retrieved 2015/09/08.
• 2、 Seung, Ho Lee,Dong, Hyun Kim,Jeong, Ah Kim,Jahng, Yurngdong. "A simple synthesis of piperlonguminine". . p. 407 - 410. Retrieved 2007/10/03.