136-72-1

Usage

Uses

Used in Pharmaceutical Industry:
5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID is used as a bioactive compound for its potential therapeutic applications. As a metabolite of Piperine, it may contribute to the overall health benefits associated with the consumption of black pepper, possibly playing a role in anti-inflammatory, antioxidant, or other medicinal properties.
Used in Research and Development:
In the field of scientific research, 5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID serves as a valuable compound for studying the chemical properties and biological activities of natural products derived from plants, such as black pepper. This can lead to the discovery of new drugs or therapeutic agents based on its unique structure and properties.
Used in Nutraceutical Applications:
Given its origin from black pepper, 5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID may be utilized in the development of nutraceutical products that aim to harness the health-promoting properties of Piperine and its metabolites. These products could include dietary supplements, functional foods, or other wellness-related applications.
Used in Cosmetics Industry:
Due to its antioxidant and anti-inflammatory potential, 5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID may find applications in the cosmetics industry as an ingredient in skincare products, hair care products, or other personal care items that target inflammation, aging, or other skin-related concerns.
Used in Flavor and Fragrance Industry:
As a component of black pepper, 5-(3,4-METHYLENEDIOXYPHENYL)-2,4-PENTADIENOIC ACID could be employed in the flavor and fragrance industry to create unique and complex scents or flavors for various products, such as perfumes, candles, or food additives.

Purification Methods

Crystallise the acid from EtOH. It turns yellow in light. It sublimes with partial decomposition. It has UV max 340nm (MeOH). [Beilstein 19 H 281, 19 II 30, 19 III/IV 3565.]

Upstream product

• 120-57-0 piperonal 
• 1462-12-0 diethyl ethylidenemalonate 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 58095-77-5 (E)-3,4-methylenedioxycinnamaldehyde 
• 495-87-4 isochavicinic acid 
• 93399-76-9 3t-(1,3-Benzodioxol-5-yl)allylidenmalonsaeure 
• 6190-46-1 methyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate 
• 94-62-2 Piperine 
• 6372-02-7 (E)-3-iodoacrylic acid 
• 54976-52-2 (2E,4E)-5-(3,4-methylenedioxyphenyl)penta-2,4-dienal 
• 67-56-1 methanol 
• 7553-56-2 iodine 
• 71-43-2 benzene 

Downstream Products

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 94-53-1 Piperonylic acid 
• 41917-45-7 5-(3',4'-methylenedioxyphenyl)pentanoic acid 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 6190-46-1 methyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate 
• 6091-43-6 all-trans-5-(3,4-Methylendioxyphenyl)-2,4-pentadiensaeureethylester 
• 94-62-2 Piperine 
• 5950-12-9 piperlonguminine 
• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 120-57-0 piperonal 
• 133-37-9 DL-tartaric acid 
• 144-62-7 oxalic acid 
• 64-19-7 acetic acid 
• 26163-80-4 (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-morpholinopenta-2,4-dien-1-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents

Nineteen novel piperine based triazoles have been synthesized using click chemistry approach and were tested for in vivo anti-inflammatory activity. The most active compounds were evaluated for in vitro TNF-α expression. Compounds 3g and 3f were found to

Amino acid amides of piperic acid (PA) and 4-ethylpiperic acid (EPA) as NorA efflux pump inhibitors of Staphylococcus aureus

A total of eighteen piperic acid (PA) and 4-ethylpiperic acid (EPA) amides (C1–C18) with α-, β- and γ-amino acids were synthesized, characterized and evaluated for their efflux pump inhibitory activity against ciprofloxacin resistant Staphylococcus aureus. The amides were screened against NorA overexpressing S. aureus SA-1199B and wild type S. aureus SA-1199 using ethidium bromide as NorA efflux pump substrate. EPI C6 was found to be most potent and reduced the MIC of ciprofloxacin by 16 fold followed by C18 which showed 4 fold reduction of MIC. Ethidium bromide efflux inhibition and accumulation assay proved these compounds as NorA inhibitors.

The larvicidal activity of natural inspired piperine-based dienehydrazides against Culex pipiens

A series of piperine-based dienehydrazide derivatives were designed and synthesized to be used as insecticides against Culex pipiens. The chemical structure of compound 5n was confirmed by single-crystal x-ray diffraction. Their insecticidal activities of

Synthetic piperine amide analogs with antimycobacterial activity

Piperine amide analogs are synthesized by replacement of the piperidine moiety with different types of cyclic amines, including adamantyl and monoterpene-derived fragments. The compounds are screened for activity against Mycobacterium tuberculosis H37Rv. The most potent compounds are the 1-adamantyl and the monoterpene-derived hybrids, which combine nanomolar antimycobacterial activity with low cytotoxicity against human cells. The presence of quaternary carbon atom as main structural requirement for anti-TB activity is pointed out by a QSAR study. The most promising compound is the (+)-isopinocampheylamine-derived amide which is characterized with selectivity index of 1387.8.

Synthesis and antimicrobial evaluation of piperic acid amides and their lower homologues

Seven piperic acid amides along with their lower homologs (12) were synthesized using HATU-DIPEA coupling reagent. All the synthesized derivatives were evaluated for their antibacterial activities against Staphylococcus aureus, Pseudomonas aeruginosa, and vancomycin-resistant P. aeruginosa. They were found to be more active on P. aeruginosa than on S. aureus. However, they did not exhibit potent activity on Vancomycin resistant P. aeruginosa. Among the tested compounds, methylenedioxycinnamic acid amide of anthranilic acid (MDCA-AA, 2a) was found to be most active against S. aureus with MIC of 3.125 μg/ml. The PAS and INH amides of piperic acid were screened against Mycobacterium tuberculosis H37Ra strain. They were found to be most active among all the tested compounds but were found to be less active than the standard drug, isoniazid.

AMIDES OF OTTONIA CORCOVADENSIS

Key Word Index-Ottonia corcovadensis; Piperaceae; amides; piperovatine; piperlonguminine; isopiperlonguminine; corcovadine; isocorcovadine; 1H NMR and mass spectrometry.Abstract-Five amides were isolated from the roots of Ottonia corcovadensis.Two are the known piperlonguminine and piperovatine.The other three are new and their structures are: (2Z,4Z)-N-isobutyl-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for isopiperlonguminine; (2E,4E)-N-(2-methyl-2-acetoxypropyl)-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for corcovadine; and (2Z,4Z)-N-(2-methyl-2-acetoxypropyl)-5-(3,4-methylenedioxyphenyl)-penta-2,4-dienoic amide for isocorcovadine.

Synthesis and insecticidal activity of new amide derivatives of piperine

The natural lipophilic amides piperine and piperiline were isolated from Piper nigrum L (Piperaceae). Piperine was hydrolysed into piperic acid (85% yield) which was converted into 16 amides (28-89% yield). The contact toxicity of all synthetic amides, and also that of piperine and piperiline, at the dose 10 μg per insect, was evaluated for the Brazilian economically important insects Ascia monuste orseis Latr, Acanthoscelides obtectus Say, Brevicoryne brassicae L, Protopolybia exigua DeSaus and Cornitermes cumulans Kollar. The results demonstrated that the insects have different sensivities to the various amides, with mortality ranging from 0 to 97.5% according to the compound and insect species. (C) 2000 Society of Chemical Industry.

Synthesis, in vitro and in silico anti-bacterial analysis of piperine and piperic ester analogues

A set of 12 analogues of piperine was designed, replacing the amide functional group of the molecule with different aliphatic and aromatic ester functional groups. Molecular docking studies of these molecules with FDA-approved target proteins for anti-bacterial drugs were done. The binding energy of the proteins and the ligands were low and the analogues were found to be drug-like based on the ADME results; hence, the molecules were synthesized. The synthesized compounds were tested for their anti-bacterial property against six bacterial species via Agar well-diffusion method. Acinetobacter baumannii, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus epidermidis were the strains tested. The overall susceptibility is higher in gram-positive. The analogues showed better activity than piperine. The analogues, propyl piperic ester (P3) and 2-fluorophenyl piperic ester (P9) and 4-fluorophenyl piperic ester (P10) showed comparatively bigger inhibition zones for all the strains.

Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs

Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.

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.