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
- Has part
- hydrogen
- Mass
- 285.136
- Image
- Piperin.jpg
Show 10 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
- physically interacts with
- Transient receptor potential cation channel subfamily V member 1
- found in taxon
- pomegranate
- Commons category
- Piperine
- has characteristic
- pungency
- described by source
- Encyclopædia Britannica 11th edition
via Wikidata · CC0
~4 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “piperine” article, available under the CC BY-SA 4.0 licence.