piperlongumine
2(1H)-pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
 
Notes:
Alkaloid from the roots of Piper longum (long pepper)
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1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one (Click)
CAS Number: 20069-09-4Picture of molecule
FDA UNII: SGD66V4SVJ
Nikkaji Web: J14.252B
MDL: MFCD00075706
XlogP3-AA: 2.10 (est)
Molecular Weight: 317.34143000
Formula: C17 H19 N O5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
bleaching agents
skin conditioning
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Suppliers:
ExtraSynthese
For experimental / research use only.
Piperlongumine (HPLC) ≥90%
Sabinsa Corporation
Piperlongumine 95%
Santa Cruz Biotechnology
For experimental / research use only.
Piperlongumine
Sigma-Aldrich: Sigma
For experimental / research use only.
Piperlongumine ≥97% (HPLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 637858
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Chemidplus: 0020069094
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References:
 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 637858
Pubchem (sid): 135231077
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10166
HMDB (The Human Metabolome Database): HMDB30341
FooDB: FDB002184
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 pepper long pepper root
Search Trop  Picture
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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
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Articles:
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.
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