piperlongumine

2(1H)-pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-

CAS: 20069-09-4 C17 H19 N O5 MW: 317.34143000

Identification

Namepiperlongumine
CAS Number20069-09-4
FDA UNIISGD66V4SVJ
Molecular FormulaC17 H19 N O5
Molecular Weight317.34143000
MDL NumberMFCD00075706
Nikkaji NumberJ14.252B

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

CosIngcosmetic data
Cosmetic Usesantioxidants

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic agents
Recommendation for piperlongumine usage levels up tonot for fragrance use.
Recommendation for piperlongumine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

pepper long pepper root

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 jiāo) 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 PI3 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.