2049. Chavicine
Nomenclature
CAS number: 495-91-0
(Z,Z)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine; (Z,Z)-1-piperoylpiperidine. C17H19NO3; mol wt 285.34.
C 71.56%, H 6.71%, N 4.91%, O 16.82%.
Description and 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).
