Structure via PubChem · Public domain (PubChem)
piperine
Sign in to saveAlso known as 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine, 1-piperoylpiperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-2,4-pentadienoyl]piperidine, (E,E)-1-piperoylpiperidine, N-[(E,E)-Piperoyl]piperidine, 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
Piperine is an alkaloid extracted from the plant, Piper nigrum. Responsible for the pungency of black pepper, it is used in food flavorings as a spice, in fragrances, as an insecticide, and as an animal pest repellent.
Key facts
- Pepper.scoville
- 150,000
via Wikipedia infobox
Chemical data
- Formula
- C17H19NO3
- Molecular weight
- 285.34 g/mol
- IUPAC name
- (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
- SMILES
- C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
- InChIKey
- MXXWOMGUGJBKIW-YPCIICBESA-N
- XLogP
- 3.5
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
2,229 papers- Piperine: A review of its biological effects.Phytotherapy research : PTR · 2021
- Curcumin-piperine co-supplementation and human health: A comprehensive review of preclinical and clinical studies.Phytotherapy research : PTR · 2023
- Piperine: Chemistry and Biology.Toxins · 2023
- Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers.Planta medica · 1998
- Black pepper and its pungent principle-piperine: a review of diverse physiological effects.Critical reviews in food science and nutrition · 2007
via PubMed
Wikidata facts
- Mass
- 285.136
- Image
- Piperin.jpg
Show 6 more facts
- melting point
- 131
- Scoville grade
- 100000
- chemical formula
- C₁₇H₁₉NO₃
- canonical SMILES
- C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
- isomeric SMILES
- C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
- Commons category
- Piperine
via Wikidata · CC0
~4 min read
Article
9 sectionsContents
- Preparation
- Extraction
- Chemical synthesis
- Biosynthesis
- Reactions
- History
- Uses
- See also
- References
Piperine is an alkaloid extracted from the plant, Piper nigrum. Responsible for the pungency of black pepper, it is used in food flavorings as a spice, in fragrances, as an insecticide, and as an animal pest repellent.
Along with its isomer chavicine, piperine from black pepper and long pepper has pungency effects via activation of TRPV1.