Piperine

Source: Wikipedia, the free encyclopedia.
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
IUPHAR/BPS
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).
☒N verify (what is checkY☒N ?)
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]

Preparation

Due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane.[5] The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers.[6][7]

Piperine can also be prepared by treating the solvent-free residue from a concentrated alcoholic extract of black pepper with a solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine).[7] The solution is decanted from the insoluble residue and left to stand overnight in alcohol. During this period, the alkaloid slowly crystallizes from the solution.[8]

Piperine has been synthesized by the action of piperonoyl chloride on piperidine.[7]

Reactions

Piperine forms salts only with strong acids. The platinichloride B4·H2PtCl6 forms orange-red needles ("B" denotes one mole of the alkaloid base in this and the following formula). Iodine in potassium iodide added to an alcoholic solution of the base in the presence of a little hydrochloric acid gives a characteristic periodide, B2·HI·I2, crystallizing in steel-blue needles with melting point 145 °C.[7]

Piperine can be

hydrolyzed by an alkali into piperidine and piperic acid.[7]

In light, especially ultra-violet light, piperine is changed into its isomers chavicine, isochavicine and isopiperine, which are tasteless.[9][2]

History

Piperine was discovered in 1819 by

Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".[11]

See also

References

  1. ISBN 9789332520264
    .
  2. ^
    S2CID 56022338
    . Retrieved 26 September 2023.
  3. ISBN 091191028X
  4. S2CID 42908718
    .
  5. doi:10.1021/ed070p598
    .
  6. ^ "Pepper". Tis-gdv.de. Retrieved 2 September 2017.
  7. ^ a b c d e Henry, Thomas Anderson (1949). "Piperine". The Plant Alkaloids (4th ed.). The Blakiston Company. p. 1-2.
  8. ISBN 0123705517
    .
  9. PMID 17661483. Retrieved 26 September 2023.{{cite journal}}: CS1 maint: numeric names: authors list (link
    )
  10. ^ Ørsted, Hans Christian (1820). "Über das Piperin, ein neues Pflanzenalkaloid" [On piperine, a new plant alkaloid]. Schweiggers Journal für Chemie und Physik (in German). 29 (1): 80–82.
  11. ASIN B00432KEP2
    .
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