7780-20-3

Basic information

• Product Name: piperine
• Synonyms: 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine;1-Piperidino-5-(1,3-benzodioxole-5-yl)-2,4-pentadiene-1-one;Piperine;Piperidine, 1-[5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl]-
• CAS NO: 7780-20-3
• Molecular Formula: C17H19NO3
• Molecular Weight: 285.37
• EINECS: 202-348-0
• Mol File: 7780-20-3.mol
• Article Data: 33

Chemical Properties

• Melting Point: 128-132℃
• Boiling Point: 498.524 °C at 760 mmHg
• Flash Point: 255.298 °C
• Appearance: /
• Density: 1.212 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• PKA: -0.71±0.20(Predicted)
• Water Solubility: 40 mg/L (18℃)
• CAS DataBase Reference: piperine(CAS DataBase Reference)
• NIST Chemistry Reference: piperine(7780-20-3)
• EPA Substance Registry System: piperine(7780-20-3)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R21/22:
• Safety Statements: S36/37:
• Hazardous Substances Data: 7780-20-3(Hazardous Substances Data)

Usage

General Description

Piperine is a natural alkaloid compound found in black pepper that is responsible for its pungent flavor. It has been found to have numerous health benefits, including anti-inflammatory, antioxidant, and anti-cancer properties. Additionally, piperine has been shown to enhance the absorption and bioavailability of other nutrients and drugs in the body, making it a valuable compound for improving overall health and wellness. It is also known for its potential to aid in weight loss and improve gastrointestinal function. Overall, piperine is a powerful and versatile chemical compound with a wide range of potential health benefits.

InChI:InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2-,7-3+

Upstream product

• 20850-43-5 5-(chloromethyl)-1,3-benzodioxole 
• 495-76-1 piperonol 
• 41193-98-0 1-(4-oxo-butyryl)-piperidine 
• 94-62-2 Piperine 
• 50838-22-7 1-crotonoylpiperidine 
• 120-57-0 piperonal 
• 110-89-4 piperidine 
• 136-72-1 piperic acid 
• 4711-72-2 piperic acid chloride 
• 98-01-1 furfural 
• 18708-18-4 furfural tosylhydrazone 
• 54976-52-2 (2E,4E)-5-(3,4-methylenedioxyphenyl)penta-2,4-dienal 
• 71627-26-4 1-<5-(1,3-benzodioxol-5-yl)-1-oxo-3,4-pentadienyl>piperidine 
• 3204-68-0 benzyldimethylphenylammonium chloride 

Downstream Products

• 136-72-1 piperic acid 
• 147429-43-4 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-2,4-pentadien-1-yl)-piperidine 
• 90778-74-8 N-piperoylglycine 
• 1087058-32-9 (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-(4-methoxyphenyl)penta-2,4-dienamide 
• 1313740-69-0 (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(3-phenylpropyl)-2,4-pentadienamide 

Relevant articles and documents

Vicinal difluorination as a C=C surrogate: An analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

Piperine, a natural product derived from peppercorns, has a variety of biological activities that make it an attractive lead compound for medicinal chemistry. However, piperine has some problematic physicochemical properties including poor aqueous solubility and a susceptibility to UV-induced degradation. In this work, we designed an analog of piperine in which the central conjugated hydrocarbon chain is replaced with a vicinal difluoroalkane moiety. We show that this fluorinated analog of piperine has superior physicochemical properties, and it also has higher potency and selectivity towards one particular drug target, acetylcholinesterase. This work highlights the potential usefulness of the threo-difluoroalkane motif as a surrogate for E-alkenes in medicinal chemistry.

An Ir3L2complex with anion binding pockets: photocatalyticE-Zisomerizationviamolecular recognition

A molecular host with photosensitizing centers provides photo-responsive host-guest properties based on its molecular recognition ability. Here, we construct a self-assembled photoactive Ir(iii) cage-shaped complex that contains anion binding pockets on its rim. The anion recognition ability of the complex enables efficient catalysis of the visible-light-inducedE-Zisomerization of an anionic styrene derivative.

Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway

Parkinson's disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogues and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogues, 3b exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of 3b might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of 3b significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopositive dopaminergic neurons. Our results provided evidence that 3b might be a promising candidate for Parkinson's disease treatment.