PIPERLONGUMINE CAS#: 20069-09-4; ChemWhat Code: 51049

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NamePIPERLONGUMINE
IUPAC Name1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Molecular StructurePIPERLONGUMINE-CAS-20069-09-4
CAS Registry Number 462-08-8
EINECS Number20069-09-4
MDL NumberMFCD00075706
SynonymsPiperlongumine
Piplartine
20069-09-4
UNII-SGD66V4SVJ
(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
SGD66V4SVJ
PPLGM
CHEBI:8241
1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
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]-
BRD2293
BRD-2293
(E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-one
Piplartine;PPLGM
Prestwick_399
MFCD00075706
FERROUSFLUOBORATE
ST079382
Prestwick2_000604
Prestwick3_000604
Piperlongumine; Piplartine
PIPERLONGUMINE [MI]
5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone
BSPBio_000508
PIPERLONGUMINE [INCI]
MLS002153903
SCHEMBL173092
SPECTRUM1505135
BPBio1_000560
CHEMBL465843
SCHEMBL2465593
1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one
ACon1_001541
CHEBI:92424
DTXSID801029762
HMS1569J10
HMS2096J10
HMS2234K24
Piperlongumine, >=97% (HPLC)
BCP13030
EX-A2925
HY-N2329
BDBM50462013
NSC794671
s7551
AKOS024284776
CCG-214375
NSC-794671
NCGC00096028-01
NCGC00096028-02
NCGC00096028-03
NCGC00096028-04
NCGC00096028-14
AC-32683
AS-74140
BP-25401
SMR001233252
CS-0021113
P2361
A14124
EN300-7424497
A920539
SR-01000841248
A1-00162
J-012992
N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one
Q7197361
SR-01000841248-2
BRD-K24132293-001-05-3
BRD-K24132293-001-09-5
BRD-K24132293-001-16-0
5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone #
1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9CI
5,6-dihydro-1-[1-oxo-3-(3,4,5-triMethoxyphenyl)-allyl]-2(1H)-pyridinone
5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-trans-2-propenyl]-2(
Molecular FormulaC17H19NO5
Molecular Weight317.34
InChIInChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChI KeyVABYUUZNAVQNPG-BQYQJAHWSA-N
Isomeric SMILESCOC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
Patent Information
Patent IDTitlePublication Date
WO2022/153306ANTI-QUORUM SENSING, ANTI-BIOFILM, AND INFLAMMATION ATTENUATING COMPOUNDS, COMPOSITIONS, AND METHODS OF USING SAME2022
WO2020/68425COMPOSITIONS AND METHODS FOR ENHANCING INSULIN SECRETION2020
WO2019/54891TRPV2 ANTAGONISTS2019
WO2019/103897DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF2019
 WO2016/14625COMPOSITIONS AND METHODS FOR SELECTIVELY DEPLETING SENESCENT CELLS2016

Physical Data

AppearanceWhite to off-white powder
Melting Point, °C
120 – 121
122 – 123
156 – 158
125 – 127
124
Density, g·cm-3
1.2
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Association with compounddimethyl sulfoxide24.84calf thymus DNA

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1H400
Chemical shifts, Spectrum13C100
Chemical shifts1Hchloroform-d1300
Chemical shifts13Cchloroform-d175
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
Bands, Spectrum
Bands, Spectrumpotassium bromide
ATR (attenuated total reflectance), Bands
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
Spectrum230, 330
Spectrumaq. phosphate buffer
Spectrum
Spectrumacetonitrile

Route of Synthesis (ROS)

Route of Synthesis (ROS) of PIPERLONGUMINE CAS 20069-09-4

Route of Synthesis (ROS) of PIPERLONGUMINE CAS 20069-09-4

ConditionsYield
Stage #1: glycine ethyl ester hydrochloric acid With triethylamine In ethanol at 20℃; for 0.5h;
Stage #2: (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one In ethanol at 20℃; for 1.5h;		78%
Stage #1: glycine ethyl ester hydrochloric acid With triethylamine In ethanol at 20℃; for 0.5h;
Stage #2: (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one In ethanol for 1.5h;

Experimental Procedure

To a stirred solution of glycine ethyl ester. HC1 (66.04 mg, 0.473 mmol) in ethanol (0.8 mL), triethylamine 48.2 mg, 0.473 mmol) was added and stirred for 30 min. To this SPL (50.0 mg, 0.157 mmol) was added and stirred at room temperature. The reaction was monitored by TLC (Hexane-ethyl acetate (1:1). Starting material consumed within 1.5 h. After completion, the reaction mixture was quenched with 5% aq. HC1 (10 mL) and extracted with ethyl acetate (2 x 20 mL), the combined organic layer was washed with water (1 x 20 mL), 5% NaHCOs solution (20 mL), water (2 x 20 mL), dried over anhyd. Na2SO4 and concentrated under reduced pressure. To the crude reaction mass, 2 mL of diethyl ether was added, and the reaction mass was filtered and dried to get pure product as white solid in 40 mg (yield 78%).		78%

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement CodesP261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight317.342
logP1.413
HBA3
HBD0
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)65.07
Rotatable Bond (RotB)6
Matching Veber Rules2
Quantitative Results
1 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceCYTOTOXIC PYRIDONE ALKALOIDS FROM PIPER ABORESCENS
2 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceALR2 INHIBITORS AND THEIR SYNTHESIS FROM A NATURAL SOURCE
3 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceA piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae.
4 of 264Comment (Pharmacological Data)Bioactivities present
ReferencePiperlongumine for Enhancing Oral Bioavailability and Cytotoxicity of Docetaxel in Triple-Negative Breast Cancer
5 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceMETHOD OF TREATING MEDULLOBLASTOMA
6 of 264Comment (Pharmacological Data)Bioactivities present
ReferencePiperlongumine induces G2/M phase arrest and apoptosis in cholangiocarcinoma cells through the ROS-JNK-ERK signaling pathway
7 of 264Comment (Pharmacological Data)Bioactivities present
Reference Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data
8 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceMild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones
9 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceAn autophagy modifier screen identifies small molecules capable of reducing autophagosome accumulation in a model of CLN3-mediated neurodegeneration
10 of 264Comment (Pharmacological Data)Bioactivities present
ReferenceCOMPOSITIONS AND METHODS FOR TREATING RAS-MUTANT CANCERS
Use Pattern
piperlongumine-cas-20069-09-4 has been used in traditional medicine as an analgesic and anti-inflammatory agent, particularly in traditional Chinese medicine. It is believed to have potential benefits for certain conditions and dietary supplement.

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