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TCI

CAS 20069-09-4

Piperlongumine TCI P2361

Piperlongumine TCI P2361

Chemical Identity

CAS No.
20069-09-4
PubChem
CID 637858·SID 354333528
Formula
C17H19NO5
Molecular weight
317.34 g/mol
Purity
>97.0%(HPLC)
Reference databases
ChEBI·ChemSpider·ECHA·Wikipedia
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
SMILES
COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
InChIKey
VABYUUZNAVQNPG-BQYQJAHWSA-N
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TCI P2361 Piperlongumine, also known as piplartine, is a naturally occurring amide alkaloid isolated from Javanese long pepper, or long pepper (Piper longum). Its structure has a 3,4,5-trimethoxycinnamoyl group attached to a dihydropyridinone ring. In the laboratory, piperlongumine is a research compound in cell biology and pharmacology. Researchers mainly use it to study oxidative stress, cancer cell death and cellular signalling pathways. The compound is widely reported in the biomedical literature, which gives researchers plenty of published work to compare against and build on.

Many researchers choose piperlongumine because it has been reported to raise levels of reactive oxygen species (ROS) selectively in cancer cells compared with normal cells. Its structure contains two Michael acceptors: the conjugated double bond in the lactam ring and the one in the cinnamoyl group. Both can react with thiol groups, such as glutathione and cysteine-containing proteins. This reactivity underlies many of the compound's biological effects. Piperlongumine is also being studied as a senolytic agent and as an inhibitor of inflammatory pathways in experimental models, so one compound can serve several research directions.

For researchers in Indonesia, piperlongumine has an added appeal because it comes from a plant known in jamu and traditional medicine. University laboratories, pharmacology and natural product research groups, and biomedical research institutes can use it as a reference compound. It links locally known medicinal plants with modern cell and molecular biology. Typical work includes in vitro studies of oxidative stress, screening of bioactive natural compounds, and comparative studies of Piper longum extracts against the isolated alkaloid.

  • Oxidative stress research: piperlongumine is reported to raise reactive oxygen species levels in cells, so it is a useful tool compound for studying redox balance and antioxidant defence mechanisms.
  • Cancer cell biology: its reported selective ROS increase in cancer cells compared with normal cells makes it relevant for studying cancer cell death mechanisms in in vitro models.
  • Thiol reactivity and glutathione studies: its two Michael acceptor sites can react with glutathione and cysteine-containing proteins, which supports research on covalent modification and thiol-dependent signalling.
  • Senolytic and inflammation research: the compound is being studied as a senolytic agent and as an inhibitor of inflammatory pathways in experimental models, which suits ageing and inflammation research programmes.
  • Natural product and ethnopharmacology studies: because it comes from Piper longum, a plant known in Indonesian jamu, it works as a reference standard when comparing plant extracts with the isolated alkaloid.

Brand TCI (product code P2361)
CAS number 20069-09-4
Molecular formula —
Purity —
Category Life Science > Biochemicals and Reagents > Alkaloids
Pack sizes available in standard TCI pack sizes; please contact AMI Scientific for current options
Physical form —
Storage follow the conditions on the TCI label and safety data sheet
  • Synonym: Piplartine

Store piperlongumine in its original, tightly closed manufacturer's container. Keep it in a cool, dry place away from direct light, heat sources and moisture, and follow the storage conditions on the TCI label and safety data sheet. Because the compound is biologically active and reacts with thiol groups, handle it in a well-ventilated area or fume hood. Wear suitable personal protective equipment, including lab coat, gloves and safety glasses. Avoid inhaling dust and avoid contact with skin and eyes. Prepare solutions with clean, compatible glassware and label them clearly. Dispose of waste according to institutional and local chemical waste regulations.

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