Piperine

Not to be confused with piperidine.
Piperine
Names
Preferred IUPAC name
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Other names
(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Piperoylpiperidine
Bioperine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.135 Edit this at Wikidata
UNII
  • InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+ ☒N
    Key: MXXWOMGUGJBKIW-YPCIICBESA-N ☒N
  • InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
    Key: MXXWOMGUGJBKIW-YPCIICBEBY
  • O=C(N1CCCCC1)\C=C\C=C\c2ccc3OCOc3c2
Properties
C17H19NO3
Molar mass 285.343 g·mol−1
Density 1.193 g/cm3
Melting point 130 °C (266 °F; 403 K)
Boiling point Decomposes
40 mg/l
Solubility in ethanol soluble
Solubility in chloroform 1 g/1.7 ml
Hazards
Safety data sheet (SDS) MSDS for piperine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Piperine
Scoville scale150,000[1] SHU

Piperine, possibly along with its isomer chavicine,[2] is the compound[3] responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine.[4]

  1. ^ Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN 9789332520264.
  2. ^ Cite error: The named reference De_Cleyn&Verzele1972 was invoked but never defined (see the help page).
  3. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, p. 7442, ISBN 091191028X
  4. ^ Srinivasan, K. (2007). "Black pepper and its pungent principle-piperine: A review of diverse physiological effects". Critical Reviews in Food Science and Nutrition. 47 (8): 735–748. doi:10.1080/10408390601062054. PMID 17987447. S2CID 42908718.