7780-20-3

Usage

Uses

Used in Pharmaceutical Industry:
Piperine is used as a bioavailability enhancer for its ability to increase the absorption and effectiveness of other drugs and nutrients in the body.
Used in Nutraceutical Industry:
Piperine is used as a dietary supplement for its health-promoting properties, such as anti-inflammatory, antioxidant, and anti-cancer effects, contributing to overall wellness and disease prevention.
Used in Weight Loss Products:
Piperine is used as an ingredient in weight loss formulations due to its potential to aid in fat reduction and improve metabolic function.
Used in Gastrointestinal Health Products:
Piperine is used as a component in gastrointestinal health products to support digestion and alleviate gastrointestinal issues.

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

• 110-89-4 piperidine 
• 67911-75-5 (E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole 
• 136055-33-9 N-<1-oxo-2-(3,6-diisopropyl-2-pyrazinylsulfinyl)ethyl>piperidine 
• 50838-22-7 1-crotonoylpiperidine 
• 120-57-0 piperonal 
• 10043-37-5 N-acrylpiperidine 
• 202998-56-9 (E)-β-iodo-3,4-methylenedioxystyrene 
• 22980-23-0 2-oxa-3-oxobicyclo[2.2.0]hex-5-ene 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 94-62-2 Piperine 
• 3204-68-0 benzyldimethylphenylammonium chloride 
• 41193-98-0 1-(4-oxo-butyryl)-piperidine 
• 495-76-1 piperonol 
• 20850-43-5 5-(chloromethyl)-1,3-benzodioxole 

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 
• 1033757-14-0 N-(2-hydroxyethyl)-3-nitro-4-[2-(piperidin-1-ylcarbonyl)pyrrol-1-yl]benzamide 
• 1033757-18-4 3-amino-4-[4-(benzo[1,3]dioxol-5-yl)-4-hydroxy-1-(piperidin-1-ylcarbonyl)but-2-enylamino]-N-(2-hydroxyethyl)benzamide 
• 1033757-01-5 C₂₄H₂₄N₄O₇ 
• 1033757-15-1 3-nitro-4-[2-(piperidin-1-ylcarbonyl)pyrrol-1-yl]benzamide 
• 1033757-21-9 3-(benzo[1,3]dioxol-5-yl)-6-(piperidin-1-ylcarbonyl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 4-carbamoylbenzyl ester 
• 1033756-91-0 6-(benzo[1,3]dioxol-5-yl)-3-(piperidin-1-ylcarbonyl)-3,6-dihydro-[1,2]oxazine-2-carboxylic acid 4-carbamoylbenzyl ester 

Relevant academic research and scientific papers

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.

The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2

Human Cytochrome P450 2J2 (CYP2J2) as an important metabolic enzyme, plays a crucial role in metabolism of polyunsaturated fatty acids (PUFAs). Elevated levels of CYP2J2 have been associated with various types of cancer, and therefore it serves as a potential drug target. Herein, using a high-throughput screening approach based on enzymic activity of CYP2J2, we rapidly and effectively identified a novel natural inhibitor (Piperine, 9a) with IC50 value of 0.44 μM from 108 common herbal medicines. Next, a series of its derivatives were designed and synthesised based on the underlying interactions of Piperine with CYP2J2. As expected, the much stronger inhibitors 9k and 9l were developed and their inhibition activities increased about 10 folds than Piperine with the IC50 values of 40 and 50 nM, respectively. Additionally, the inhibition kinetics illustrated the competitive inhibition types of 9k and 9l towards CYP2J2, and K i were calculated to be 0.11 and 0.074 μM, respectively. Furthermore, the detailed interaction mechanism towards CYP2J2 was explicated by docking and molecular dynamics, and our results revealed the residue Thr114 and Thr 315 of CYP2J2 were the critical sites of action, moreover the spatial distance between the carbon atom of ligand methylene and Fe atom of iron porphyrin coenzyme was the vital interaction factor towards human CYP2J2.

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.

Piperine derivative as well as preparation method and application thereof

The invention provides a piperine derivative as well as a preparation method and an application thereof. The piperine derivative is a compound shown as a formula (I), or a salt thereof, or a stereoisomer thereof, or a hydrate thereof. The compound provided by the invention can effectively protect nerve cells and improve the survival rate of the nerve cells, so that the compound provided by the invention can effectively treat neurodegenerative diseases and can be used for preparing medicines for treating the neurodegenerative diseases.

A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues

A quantitative synthesis of piperine from commercially available starting material is presented. The synthesis relies on a stereoselective nucleophilic attack of an in situ generated cuprate onto a cyclobutene lactone. The so-formed aryl-substituted cyclobutene spontaneously undergoes a conrotatory 4π-electrocyclic ring opening to form the 4-aryl pentadienoic acid as a single diastereoisomer. The high-yielding synthesis can be easily modulated on the aryl and on the amide moiety for the synthesis of a wide range of piperine analogues.

Piperine synthesis method

The invention discloses a piperine synthesis method. According to the synthesis method, 5-(1,2-methylenedioxyphenyl)-2-pentenal is taken as the primary raw material; a palladium catalyst is used, oxygen is taken as the oxidizing agent, trifluoroacetic acid is taken as the additive, in a polar organic solvent, one-step oxidation-dehydrogenation is performed to obtain 5-(1,2-methylenedioxyphenyl)-2,4-dipentenal, then oxidation and amidation are carried out to obtain piperine, and the yield is high. The key step namely palladium is used to catalyze oxidation-dehydrogenation is realized, and piperine can be synthesized efficiently and concisely. Compared with a conventional method, the operation is simple, the reaction yield is higher, the method is environmentally friendly, the yield is high,and the atom utilization rate is high.

PROCESS FOR THE PREPARATION OF PIPERINE

The present application relates to a process for the preparation of piperine of high purity having low concentrations of isomeric impurities.

Synthesis, antimicrobial, antioxidant and nematicidal activity of (2E,4E)-5-(Benzo[d] [1,3]dioxol-5yl)penta-2,4-dienamides

The amides of piperic acid have been synthesized via the condensation of piperic acid with amines. The structural characterization was done by IR, 1H-NMR, EI-MS and elemental analysis. The amides 3a-3o were evaluated for their biological activity. It has been found that among others the newly synthesized compound 3f, 3k, 3m, and 3o have great potential against root-knot nematode Meloidogyne incognita that usually affect tomato crop. These compounds exhibited 92, 96, 82 and 95% mortality rate at lethal concentration (LC50) 4.4, 3.4, 4.5 and 3.5 mg/mL, respectively. Conventionally used nematicide furadan was taken as standard. Compound 3h, 3c and, 3j exhibited significant anti-oxidant activities against 1,1-diphenylpicrylhydrazil (DPPH) radical with 80, 70 and 72% inhibition (EC50 = 625, 937 and 937.5 μg/mL), respectively. Ascorbic acid was used as standard. When tested for antimicrobial activity 3m was found to be the most active one showing zone of inhibition in the range of 18-30 mm against all tested microbial strains. Good biological activities of synthetic amides indicate their ability to behave as a good antimicrobial and nematicidal agent.

A metal-free approach for transamidation of amides with amines in aqueous media

An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).