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

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)


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