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Piperine
From Wikipedia, the free encyclopedia
| Piperine | |
|---|---|
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| Systematic name | 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo- 2,4-pentadienyl]piperidine |
| Chemical formula | C17H19NO3 |
| Molecular mass | 285.338 g/mol |
| Density | 1.193 g/cm3 |
| Melting point | 130 °C |
| Boiling point | decomposes |
| CAS number | [94-62-2] |
| SMILES | O=C(/C=C/C=C/C2=CC=C (OCO3)C3=C2)N1CCCCC1 |
| Disclaimer and references | |
Piperine is the alkaloid responsible for the pungency of black pepper along with chavicine (an isomer of piperine). It has also been used in some forms of traditional medicine and as an insecticide.
The pungency caused by capsaicin and piperidine is caused by activation of the heat and acidity sensing TRPC ion channel TRPC1 on nociceptorss (pain sensing nerve cells).
Piperine has also been found to inhibit human CYP3A4 and P-glycoprotein, enzymes important for the metabolism and transport of xenobiotics and metabolites (PMID 12130727). In animal studies, piperine also inhibited other enzymes important in drug metabolism (PMID 3917507, PMID 8347144). By inhibiting drug metabolism, piperine may increase the bioavailability of various compounds. Notably, piperine may enhance bioavailability of curcumin by 2000% in humans (PMID 9619120).
Due to its effects on drug metabolism, piperine should be taken cautiously (if at all) by individuals taking other medications.
- Merck Index, 11th Edition, 7442.
- MSDS for piperine
- PDRhealth.com - Piperine
- Links to external chemical sources
- Piperidine, a cyclic six-membered amine that results from hydrolysis of piperine
- Capsaicin, the active piquant chemical in chile peppers
- Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish and wasabi
- Allicin, the active piquant flavor chemical in uncooked garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)