94-62-2 Usage
Description
Piperine is an alkaloid that is responsible for the taste and flavor of pepper. It exists in pure form as a yellow to pale-yellow crystal, with a burning taste and pungent odor. Piperine is found naturally in plants in the Piperaceae family, particularly Piper nigrum (black pepper) and Piper longum (Indian long pepper).
Uses
Used in Pest Control:
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 taste them.
Used in Insecticides:
Piperine is also incorporated with other compounds to make insecticides. It is effective against houseflies, lice, and various other pests.
Used in Medicine:
Piperine has been used medicinally for thousands of years and continues to be used today. It is used to treat asthma and chronic bronchitis. It also has putative analgesic and anti-inflammatory properties that stem from its antioxidant properties. Research is examining the use of piperine in treating malaria.
Used in Epilepsy Treatment:
Antiepilepsirine, a derivative of piperine, is used to treat different types of epilepsy, especially in China.
Used in Enhancing Bioavailability:
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.
Used in the Food Industry:
As an organic insecticide, Piperine is used to protect crops from pests, ensuring the quality and safety of food products.
Used in Pharmaceutical Research:
Piperine is used as a TRPV1 activator in black pepper extract, which has potential applications in the development of new drugs and therapies.
History
Hans Christian Oersted (1777 1851) isolated piperine from black pepper in 1819 and published his findings in 1820. Oersted extracted a resin from pepper plants with alcohol, formed a soluble saltby adding hydrochloric acid with alcohol, and then separated piperine from solution by precipitation and distillation. In 1882, Leopold Rügheimer (1850 1917) synthesized piperine from piperinic acid chloride and piperidine. The complete synthesis of piperine was reported in 1894 by Albert Ladenburg (1842 1911) and M. Scholtz. Ladenburg and Scholtz used piperonal (C8H6O3) and acetaldehyde (CH3CHO) to produce piperinic acid (C12H10O4), which was then reacted with thionyl chloride (COCl2) and piperidine (C5H11N) to produce piperine.
Preparation
From piperoyl chloride and piperidine.
Safety Profile
Poison by ingestion and
intraperitoneal routes. An experimental
teratogen. Experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx.
Purification Methods
Piperine crystallises as light yellow crystals from EtOH or EtOAc (m 132o), aqueous EtOH (m 128-129o), Et2O (m129o), or*benzene/ligroin. [Beilstein 20 H 79, 20 I 23, 20 II 53, 20 III/IV 1341, 20/3 V 469.]
References
Oersred., Schweigger's Journal, 29, 80 (1819)
Fliickiger, Hanbury., Pharmacographica, 584 London (1879)
Stenhouse., Pharm. J., 14,363 (1855)
Cazeneuve, Caillot., Bull. Soc. Chim. Fr., 27,291 (1877)
Riigheimer., Ber., 15, 1391 (1882)
Peinemann., Arch. Pharm., 234, 245 (1896)
Newman., Chem. Products, 16,379 (1953)
Check Digit Verification of cas no
The CAS Registry Mumber 94-62-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 94-62:
(4*9)+(3*4)+(2*6)+(1*2)=62
62 % 10 = 2
So 94-62-2 is a valid CAS Registry Number.
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+
94-62-2Relevant articles and documents
The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2
Tian, Xiangge,Zhou, Meirong,Ning, Jing,Deng, Xiaopeng,Feng, Lei,Huang, Huilian,Yao, Dahong,Ma, Xiaochi
, p. 737 - 748 (2021/03/16)
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.
Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson's disease via the activation of Nrf2/keap1 pathway
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
, (2020/05/11)
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.
A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues
Bauer, Adriano,Nam, Jun-Hyun,Maulide, Nuno
, p. 413 - 416 (2019/02/26)
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.
