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| 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)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.002.135 |
| EC Number |
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| 341351 | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| |
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| 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 | |
| GHS labelling:[1] | |
| |
| Danger | |
| H301 | |
| P264, P270, P301+P316, P321, P330, P405, P501 | |
| 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).
| |
| Piperine | |
|---|---|
| Scoville scale | 150,000[1] SHU |
Piperine is an alkaloid extracted from the plant, Piper nigrum.[2] 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.[2]
Along with its isomer chavicine,[3] piperine from black pepper and long pepper has pungency effects via activation of TRPV1.[4][5]
It has been used in some forms of traditional medicine.[6] It can be acutely toxic if swallowed in high doses.[2]
Preparation
Extraction
Due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane[7] or ethanol.[8] The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers.[9][10]
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).[10] 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.[11]
Chemical synthesis
Piperine has been synthesized by the reaction of piperonoyl chloride with piperidine.[10]
Biosynthesis
The biosynthesis of piperine is only partially known.[12]
- The last step is catalyzed by piperine synthase (piperoyl-CoA:piperidine piperoyl transferase). As suggested by its systematic name, it converts piperoyl-CoA and piperidine into piperine.
- Piperoyl-CoA is made by piperoyl-CoA ligase from piperic acid, which is in turn made from feruperic acid by CYP719A37.
- Feruperic acid is presumably made from ferulic acid. Piperine is presumably made from lysine.
In addition to piperine synthase PipBAHD2, there is an orthologous enzyme with broader substract specificity in Piper nigrum with gene symbol PipBAHD1, called a "piperamide synthase". This other enzyme is responsible for the many piperamide compounds (see [13]) besides piperine found in black pepper. Both enzymes are BAHD acyltransferases.[12]
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.[10]
Piperine can be hydrolyzed by an alkali into piperidine and piperic acid.[10]
In light, especially ultraviolet light, piperine is changed into its isomers chavicine, isochavicine and isopiperine, which are tasteless.[14][3]
History
Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of Piper nigrum, the source plant of both black and white pepper.[15] Piperine was also found in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".[16]
Uses
Piperine gives black pepper its pungency properties, making it favorable in food flavorings as a spice and in fragrances.[2] It can be used as an insecticide and to deter animal pests.[2]
See also
- Piperidine, a cyclic six-membered amine that results from hydrolysis of piperine
- Piperic acid, the carboxylic acid also derived from hydrolysis of piperine
- Capsaicin, the active piquant chemical in chili peppers
- Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish, and wasabi
- Allicin, the active piquant flavor chemical in raw garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
- Ilepcimide
- Piperlongumine
References
- ^ Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN 9789332520264.
- ^ a b c d e "Piperine". PubChem, US National Library of Medicine. 14 February 2026. Retrieved 18 February 2026.
- ^ a b De Cleyn, R; Verzele, M (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers" (PDF). Chromatografia. 5: 346–350. doi:10.1007/BF02315254. S2CID 56022338. Retrieved 26 September 2023.
- ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. p. 7442. ISBN 091191028X.
- ^ Dong, Y; Yin, Y; Vu, S; Yang, F; Yarov-Yarovoy, V; Tian, Y; Zheng, J (20 August 2019). "A distinct structural mechanism underlies TRPV1 activation by piperine". Biochemical and Biophysical Research Communications. 516 (2): 365–372. Bibcode:2019BBRC..516..365D. doi:10.1016/j.bbrc.2019.06.039. PMC 6626684. PMID 31213294.
- ^ 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.
- ^ Epstein, William W.; Netz, David F.; Seidel, Jimmy L. (1993). "Isolation of Piperine from Black Pepper". J. Chem. Educ. 70 (7): 598. Bibcode:1993JChEd..70..598E. doi:10.1021/ed070p598.
- ^ Chen∗, Zhe; Wu∗, Jian Bing; Zhang, Jie; Li, Xiao Juan; Shen, Min He (2 June 2009). "One Step Purification of Piperine Directly from Piper nigrum L. by High Performance Centrifugal Partition Chromatography". Separation Science and Technology. 44 (8): 1884–1893. doi:10.1080/01496390902775877.
- ^ "Pepper". Tis-gdv.de. Retrieved 2 September 2017.
- ^ a b c d e Henry, Thomas Anderson (1949). "Piperine". The Plant Alkaloids (4th ed.). The Blakiston Company. pp. 35–37.
- ^ Ikan, Raphael (1991). Natural Products: A Laboratory Guide (2nd ed.). San Diego, CA: Academic Press. pp. 223–224. ISBN 0123705517.
- ^ a b Schnabel, Arianne; Athmer, Benedikt; Manke, Kerstin; Schumacher, Frank; Cotinguiba, Fernando; Vogt, Thomas (8 April 2021). "Identification and characterization of piperine synthase from black pepper, Piper nigrum L." Communications Biology. 4 (1): 445. doi:10.1038/s42003-021-01967-9. PMC 8032705. PMID 33833371.
- ^ Vargas-Huertas, Luis Felipe; Alvarado-Corella, Luis Diego; Sánchez-Kopper, Andrés; Araya-Sibaja, Andrea Mariela; Navarro-Hoyos, Mirtha (9 December 2023). "Characterization and Isolation of Piperamides from Piper nigrum Cultivated in Costa Rica". Horticulturae. 9 (12): 1323. doi:10.3390/horticulturae9121323.
- ^ Kozukue N, Park MS, et al. (2007). "Kinetics of Light-Induced Cis−Trans Isomerization of Four Piperines and Their Levels in Ground Black Peppers as Determined by HPLC and LC/MS". J. Agric. Food Chem. 55 (17): 7131–7139. Bibcode:2007JAFC...55.7131K. doi:10.1021/jf070831p. PMID 17661483. Retrieved 26 September 2023.
- ^ 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.
- ^ Friedrich A. Fluckiger; Daniel Hanbury (1879). Pharmacographia : a History of the Principal Drugs of Vegetable Origin, Met with in Great Britain and British India. London: Macmillan. p. 584. ASIN B00432KEP2.
