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 isomers of piperine.

Quick facts Names, Identifiers ...

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

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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]