piperlongumine
2(1H)-pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
Identification
| Name | piperlongumine |
| CAS Number | 20069-09-4 |
| FDA UNII | SGD66V4SVJ |
| Molecular Formula | C17 H19 N O5 |
| Molecular Weight | 317.34143000 |
| MDL Number | MFCD00075706 |
| Nikkaji Number | J14.252B |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 475.61 °C. @ 760.00 mm Hg (est) |
| Flash Point | 467.00 °F. TCC ( 241.40 °C. ) (est) |
| logP (o/w) | 2.340 (est) |
| Soluble in | water, 1030 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antioxidants |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic agents |
| Recommendation for piperlongumine usage levels up to | not for fragrance use. |
| Recommendation for piperlongumine flavor usage levels up to | not for flavor use. |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Glentham Life Sciences Ltd
The Chemical, Biochemical & Research Essentials Supplier
Glentham Life Sciences is a supplier of fine chemicals and raw materials with warehousing, laboratories and packaging facilities in the UK.
Potential Uses
Natural Occurrence
Synonyms
2(1H)-
pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
2(1H)-
pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
1-[3-(3,4,5-
trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one
1-[(2E)-3-(3,4,5-
trimethoxyphenyl)prop-2-enoyl]-1,5,6-trihydropyridin-2-one
1-[(E)-3-(3,4,5-
trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
1-[(2E)-3-(3,4,5-
trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
PubMed:
Dealing Naturally with Stumbling Blocks on Highways and Byways of TRAIL Induced Signaling.
PubMed:
Piperlongumine-induced phosphatidylserine translocation in the erythrocyte membrane.
PubMed:
Impact of DNA repair pathways on the cytotoxicity of piperlongumine in chicken DT40 cell-lines.
PubMed:
Piperlongumine selectively kills cancer cells and increases cisplatin antitumor activity in head and neck cancer.
PubMed:
Piperlongumine inhibits the proliferation and survival of B-cell acute lymphoblastic leukemia cell lines irrespective of glucocorticoid resistance.
PubMed:
Redox-directed cancer therapeutics: Taurolidine and Piperlongumine as broadly effective antineoplastic agents (review).
PubMed:
Piperlongumine Chemosensitizes Tumor Cells through Interaction with Cysteine 179 of IκBα Kinase, Leading to Suppression of NF-κB-Regulated Gene Products.
PubMed:
Targeting antioxidants for cancer therapy.
PubMed:
Piperlongumine induces cell death through ROS-mediated CHOP activation and potentiates TRAIL-induced cell death in breast cancer cells.
PubMed:
Piperlongumine inhibits migration of glioblastoma cells via activation of ROS-dependent p38 and JNK signaling pathways.
PubMed:
Design, synthesis and biological activity of piperlongumine derivatives as selective anticancer agents.
PubMed:
Piperlongumine induces apoptosis and synergizes with cisplatin or paclitaxel in human ovarian cancer cells.
PubMed:
Piperlongumine treatment inactivates peroxiredoxin 4, exacerbates endoplasmic reticulum stress, and preferentially kills high-grade glioma cells.
PubMed:
Anticancer principles from medicinal piper ( hú jiÄo) plants.
PubMed:
Piperlongumine as a potential activator of AMP-activated protein kinase in HepG2 cells.
PubMed:
Piperlongumine alleviates lupus nephritis in MRL-Fas(lpr) mice by regulating the frequency of Th17 and regulatory T cells.
PubMed:
Radio-sensitization by Piper longumine of human breast adenoma MDA-MB-231 cells in vitro.
PubMed:
Piperlongumine, an alkaloid causes inhibition of PI3Â K/Akt/mTOR signaling axis to induce caspase-dependent apoptosis in human triple-negative breast cancer cells.
PubMed:
Drug-repositioning screening identified piperlongumine as a direct STAT3 inhibitor with potent activity against breast cancer.
PubMed:
Biodegradable nanoassemblies of piperlongumine display enhanced anti-angiogenesis and anti-tumor activities.
PubMed:
Piperlongumine promotes autophagy via inhibition of Akt/mTOR signalling and mediates cancer cell death.
PubMed:
Optimization and comprehensive characterization of a faithful tissue culture model of the benign and malignant human prostate.
PubMed:
Synthesis of piperlogs and analysis of their effects on cells.
PubMed:
Piperlongumine inhibits NF-κB activity and attenuates aggressive growth characteristics of prostate cancer cells.
PubMed:
Piperlongumine induces autophagy by targeting p38 signaling.
PubMed:
Targeting aberrant glutathione metabolism to eradicate human acute myelogenous leukemia cells.
PubMed:
An improved quantitative approach for the assessment of mitochondrial fragmentation in chemoresistant ovarian cancer cells.
PubMed:
Piperlongumine selectively kills glioblastoma multiforme cells via reactive oxygen species accumulation dependent JNK and p38 activation.
PubMed:
ROS inhibitor N-acetyl-L-cysteine antagonizes the activity of proteasome inhibitors.
PubMed:
Piperlongumine inhibits LMP1/MYC-dependent mouse B-lymphoma cells.
PubMed:
Antioxidants: friends or foe in prevention or treatment of cancer: the debate of the century.
PubMed:
Activation of ERK signaling and induction of colon cancer cell death by piperlongumine.
PubMed:
Discovery of small-molecule enhancers of reactive oxygen species that are nontoxic or cause genotype-selective cell death.
PubMed:
Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells.
PubMed:
Overview of the therapeutic potential of piplartine (piperlongumine).
PubMed:
Piperlongumine inhibits proliferation and survival of Burkitt lymphoma in vitro.
PubMed:
Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling.
PubMed:
Quantitative microtiter fibronectin fibrillogenesis assay: use in high throughput screening for identification of inhibitor compounds.
PubMed:
Synthesis, cellular evaluation, and mechanism of action of piperlongumine analogs.
PubMed:
Specific 5-hydroxylation of piperlongumine by Beauveria bassiana ATCC 7159.
PubMed:
A novel flow cytometric HTS assay reveals functional modulators of ATP binding cassette transporter ABCB6.
PubMed:
Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells.
PubMed:
Selective killing of cancer cells by a small molecule targeting the stress response to ROS.
PubMed:
Overview for various aspects of the health benefits of Piper longum linn. fruit.
PubMed:
Antiplatelet effects of piplartine, an alkamide isolated from Piper tuberculatum: possible involvement of cyclooxygenase blockade and antioxidant activity.
PubMed:
Antiplatelet activities of newly synthesized derivatives of piperlongumine.
PubMed:
Antiplatelet effects of acidamides isolated from the fruits of Piper longum L.
PubMed:
Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist.
PubMed:
Suppression of ochratoxin biosynthesis by naturally occurring alkaloids.
PubMed:
Amides from Piper nigrum L. with dissimilar effects on melanocyte proliferation in-vitro.
PubMed:
A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae.
PubMed:
Alkaloids of Piper longum Linn. I. Structure and synthesis of piperlongumine and piperlonguminine.