Chavicine

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 isomersofpiperine.

Chavicine
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
CAS Number	495-91-0^Y
3D model (JSmol)	Interactive image
ChemSpider	1265935^Y
ECHA InfoCard	100.230.650
PubChem CID	1548912
UNII	95JV386FPD^Y
CompTox Dashboard (EPA)	DTXSID301023602
InChI 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-^Y Key: MXXWOMGUGJBKIW-PORYWJCVSA-N^Y 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
SMILES O=C(N1CCCCC1)\C=C/C=C\c2ccc3OCOc3c2
Properties
Chemical formula	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). Y verify (what is ^YN ?) Infobox references

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]

References

^ 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.

^ De Cleyn, R; Verzele, M (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers" (PDF). Chromatografia. 5: 346–350. Retrieved 26 September 2023.

^ 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.

^ 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)

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Last edited on 13 December 2023,

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Chavicine

See also

References

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