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

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Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a potent irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent crystalline solid.

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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. doi:10.1007/BF02315254 . 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. doi:10.1016/j.medidd.2020.100027 . 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. doi:10.1021/jf070831p. PMID   17661483 . Retrieved 26 September 2023.{{cite journal}}: CS1 maint: numeric names: authors list (link)