Chavicine

Title: Chavicine
CAS Registry Number: 495-91-0
CAS Name: (Z,Z)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
Additional Names: (Z,Z)-1-piperoylpiperidine
Molecular Formula: C17H19NO3
Molecular Weight: 285.34
Percent Composition: C 71.56%, H 6.71%, N 4.91%, O 16.82%
Literature References: One of the most active constituents of black pepper: Buchheim, Arch. Exp. Pathol. Pharmakol. 5, 455 (1876); Ott, Eichler, Ber. 55, 2653 (1922); Ott, Lüdemann, Ber. 57, 214 (1924). Stereoisomer of piperine: Lohaus, Gall, Ann. 517, 282 (1935). Loss of pungency of ground pepper during storage attributed to gradual isomerization of chavicine into piperine, q.v.: Newman, Chem. Prod. 16, 379 (1953). Synthesis of chavicine and questioning of its existence as constituent of black pepper: R. Grewe et al., Ber. 103, 3752 (1970). Spectroscopic structural elucidation and prepn: R. DeCleyn, M. Verzele, Bull. Soc. Chim. Belg. 84, 435 (1975).
Properties: Yellowish, oily mass; sharp, peppery taste. Sol in alc, ether, petr ether. uv max (methanol): 318 nm (e 16200).
Absorption maximum: uv max (methanol): 318 nm (e 16200)
Chavicol Cheirolin Chelerythrine Chelidonic Acid Chelidonine

Chavicine
Chavicine.png
Identifiers
CAS number 495-91-0 YesY
PubChem 1548912
ChemSpider 1265935 YesY
Jmol-3D images Image 1
Properties
Molecular formula C17H19NO3
Molar mass 285.338 g/mol
Density 1.211 g/mL
Boiling point 498.5 °C; 929.3 °F; 771.6 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chavicine is an alkaloid found in black pepper and other species of the genus Piper. It is one of the four diastereomeric geometric isomers of piperine.