Piperine

Base Information

• Chemical Name: Piperine
• CAS No.: 94-62-2
• Deprecated CAS: 147030-08-8
• Molecular Formula: C17H19NO3
• Molecular Weight: 285.343
• Hs Code.: 29399990
• European Community (EC) Number: 202-348-0
• NSC Number: 757803,21727
• UNII: U71XL721QK
• DSSTox Substance ID: DTXSID3021805
• Nikkaji Number: J4.701E,J50.666D
• Wikipedia: Piperine
• Wikidata: Q414501
• NCI Thesaurus Code: C72629
• RXCUI: 1311146
• Pharos Ligand ID: FADZPFWWP81W
• Metabolomics Workbench ID: 43799
• ChEMBL ID: CHEMBL43185
• Mol file: 94-62-2.mol

Synonyms:((1-5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine;(1-(5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine;1-piperoylpiperidine;piperine;piperine, (E,E)-isomer;piperine, (E,Z)-isomer;piperine, (Z,E)-isomer;piperine, (Z,Z)-isomer

Chemical Property of Piperine

Chemical Property:

• Appearance/Colour: slightly yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 131-135 °C(lit.)
• Refractive Index: 1.615
• Boiling Point: 498.5 °C at 760 mmHg
• PKA: 12.22(at 18℃)
• Flash Point: 255.3 °C
• PSA: 38.77000
• Density: 1.211 g/cm³
• LogP: 2.93510
• Storage Temp.: Refrigerator
• Solubility.: 0.04g/l
• Water Solubility.: 40 mg/L (18 ºC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 285.13649347
• Heavy Atom Count: 21
• Complexity: 412

Purity/Quality:

Assay99%, ^*data from raw suppliers

Piperine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,N
• Statements: 22-21/22-20/21/22-51/53
• Safety Statements: 22-24/25-36/37-36-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Food Additives
• Canonical SMILES: C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
• Isomeric SMILES: C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
• Recent ClinicalTrials: Effect Of Piperine In Patients With Oropharyngeal Dysphagia
• Recent NIPH Clinical Trials: Study on blood pressure lowering power of health food
• Description: Piperine is an alkaloid responsible for the taste and fl avor of pepper. In pure form it exists as a yellow to pale-yellow crystal, with a burning taste and pungent order. It is found naturally in plants in the Piperaceae family, particularly Piper nigrum (black pepper) and Piper longum (Indian long pepper). Piper nigrum is a perennial woody vine that grows to approximately 30 feet. It produces spikelike flowers that hold berries called peppercorns.
• Uses: Piperine is used in granular formulations as a pesticide against small animals such as dogs, cats, skunks, raccoons, and squirrels. Piperine pesticides are nontoxic and operate as a repellant when animals smell or test them. Piperine is also incorporated with other compounds to make insecticides; it is effective against houseflies, lice, and various other pests. Piperine has been used medicinally for thousands of years and this continues today. It is used to treat asthma and chronic bronchitis. It also has putative analgesic and antiinfl ammatory properties that stem from its antioxidant properties. Research is examining the use of piperine in treating malaria. Antiepilepsirine is a derivative of piperine that is used to treat different types of epilepsy, especially in China. A current area of interest is the efficacy of piperine in increasing the bioavailability of certain nutrients and drugs. It is thought to possibly aid digestion and increase the absorption in the digestive tract of numerous drugs used as cancer treatments, antihistamines, steroidal inflammation reducers, and antibiotics. The alkaloid which gives pepper its spiciness, and has been used as an organic insecticide. A black pepper extract TRPV1 activator

Technology Process of Piperine

There total 53 articles about Piperine 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: 95.0%

piperidine (110-89-4) + piperic acid (136-72-1) → Piperine (94-62-2,7780-20-3)

Guidance literature:

piperic acid; With thionyl chloride; In dichloromethane; at 20 ℃; Schlenk technique;

piperidine; In dichloromethane; at 20 ℃; for 1h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1055/s-0037-1611652

Reference yield: 95.0%

1-crotonoylpiperidine (50838-22-7) + piperonal (120-57-0,30024-74-9) → Piperine (94-62-2,7780-20-3)

Guidance literature:

With Aliquat 336; potassium carbonate; In toluene; at 90 ℃; for 10h;

Reference yield: 90.0%

piperidine (110-89-4) + Bestmann ylide (73818-55-0,15596-07-3) + (E)-3,4-methylenedioxycinnamaldehyde (58095-77-5,14756-00-4,821775-38-6) → Piperine (94-62-2,7780-20-3)

Guidance literature:

In tetrahydrofuran; for 24h; Heating;

DOI:10.1039/b105745f

upstream raw materials:

Acetic acid 1-(benzenesulfonyl-benzo[1,3]dioxol-5-yl-methyl)-4-oxo-4-piperidin-1-yl-butyl ester

piperidine

5-(chloromethyl)-1,3-benzodioxole

piperonol

Downstream raw materials:

piperine

piperic acid

tetrahydropiperine

N-nitrosopiperidine

Refernces

• 1、 Cai, Xiaoying,Chen, Lijuan,Hong, Feng,Kuang, Shuang,Li, Yan,Ma, Xu,Qi, Wenyan,Shi, Mingsong,Wang, Lun,Xu, Ruiling,Xue, Linlin,Ye, Haoyu,Zhang, Ruijia. "Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway". . . Retrieved 2020/05/11.
• 2、 Lizarme-Salas, Yuvixza,Ariawan, Alexandra Daryl,Ratnayake, Ranjala,Luesch, Hendrik,Finch, Angela,Hunter, Luke. "Vicinal difluorination as a C=C surrogate: An analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity". . p. 2663 - 2670. Retrieved 2020/12/31.