Chavicine

Last updated
Chavicine
Chavicine.png
Names
Preferred IUPAC name
(2Z,4Z)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Other names
(2Z,4Z)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.230.650 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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- Yes check.svgY
    Key: MXXWOMGUGJBKIW-PORYWJCVSA-N Yes check.svgY
  • 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-PORYWJCVBA
  • O=C(N1CCCCC1)\C=C/C=C\c2ccc3OCOc3c2
Properties
C17H19NO3
Molar mass 285.343 g·mol−1
Density 1.211 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Chavicine is a possibly pungent compound found in black pepper [1] and other species of the genus Piper. It is one of the four geometric isomers of piperine.

In light, especially ultra-violet light, chavicine is formed from its isomer piperine. Its flavor has been reported as flavorless [2] [3] Chavicine will also re-isomerise back to piperine. [4]

See also

Related Research Articles

<i>Piper</i> (plant) Genus of plants

Piper, the pepper plants or pepper vines, is an economically and ecologically important genus in the family Piperaceae.

<span class="mw-page-title-main">Piperidine</span> Chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

<span class="mw-page-title-main">Black pepper</span> Ground fruit of the family Piperaceae

Black pepper is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about 5 mm (0.20 in) in diameter, dark red, and contains a stone which encloses a single pepper seed. Peppercorns and the ground pepper derived from them may be described simply as pepper, or more precisely as black pepper, green pepper, or white pepper.

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<span class="mw-page-title-main">Piperaceae</span> Family of flowering plants in the order Piperales

The Piperaceae, also known as the pepper family, are a large family of flowering plants. The group contains roughly 3,600 currently accepted species in 5 genera. The vast majority of species can be found within the two main genera: Piper and Peperomia.

<span class="mw-page-title-main">Piperine</span> Alkaloid responsible for the pungency of black pepper

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

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<span class="mw-page-title-main">Long pepper</span> Species of plant cultivated for its fruit which is used as a spice

Long pepper, sometimes called Indian long pepper or pippali, is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. Long pepper has a taste similar to, but sweeter and less pungent than, that of its close relative Piper nigrum – from which black, green and white pepper are obtained.

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<i>Piper guineense</i> Species of flowering plant

Piper guineense is a West African species of Piper; the spice derived from its dried fruit is known as Ashanti pepper, Benin pepper, Edo pepper, false cubeb, Guinea cubeb, and called locally kale, kukauabe, masoro, etiñkeni, sasema, soro wisa, eyendo, eshasha by the Urhobo people, and oziza and uziza by the Igbo people of Nigeria. It is a close relative of cubeb pepper and a relative of black pepper and long pepper. Unlike cubeb, which is large and spherical in shape, Ashanti pepper grains are prolate spheroids, smaller and smoother than Cubeb pepper in appearance and generally bear a reddish tinge. The stalks of Ashanti pepper berries are also distinctly curved whilst those of cubeb pepper are completely straight. The terms West African pepper and Guinea pepper have also been used, but are ambiguous and may refer to grains of Selim or grains of paradise.

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<span class="mw-page-title-main">Ilepcimide</span> Chemical compound

Ilepcimide, also known as antiepilepserine, is an anticonvulsant. It is a piperidine derivative that was first synthesized by Chinese researchers as an analogue of piperine, the main pungent compound and phytochemical of black pepper.

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References

  1. Mărutoiu, Constantin; Gogoasa, Ioan; Oprean, Ioan; Mărutoiu, Olivia-Florena; Moise, Maria-Ioana; Tigae, Cristian; Rada, Maria (2006). "Separation and identification of piperine and chavicine in black pepper by TLC and GC-MS". Journal of Planar Chromatography: Modern TLC. 19 (109): 250–252. doi:10.1556/JPC.19.2006.3.16. S2CID   97700546.
  2. De Cleyn, R; Verzele, M (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers" (PDF). Chromatografia. 5: 346–350. Retrieved 26 September 2023.
  3. Tiwari, Anshuly; Mahadik, Kakasaheb R.; Gabhe, Satish Y. (2020). "Piperine: A comprehensive review of methods of isolation, purification, and biological properties". Medicine in Drug Discovery. 7: 100027. Retrieved 26 September 2023.
  4. Kozukue, Nobuyuki; Park, Mal-Sun; others, and 5 (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. Retrieved 26 September 2023.{{cite journal}}: CS1 maint: numeric names: authors list (link)