7472. Piperine

Nomenclature

CAS number: 94-62-2
1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine; (E,E)-1-piperoylpiperidine.
C17H19NO3; mol wt 285.34.
C 71.56%, H 6.71%, N 4.91%, O 16.82%.

Description and references

Isolated from black pepper (Piper nigrum L.); also in P. longum L., P. retrofractum Vahl. (P. officinarum C.D.C.), and P. clusii C.D.C.; in root bark of Piper geniculatum Sw., Piperaceae. Extraction procedure: Cazeneuve, Caillot, Bull. Soc. Chim. [2] 27, 291 (1877). Synthesis: Rugheimer, Ber. 15, 1390 (1882); Newman, Chem. Prod. 16, 379 (1953); Normant, Feugeas, Compt. Rend. 258, 2846 (1964). Spectroscopic structural elucidation and preparative separation of piperine and its stereoisomers isopiperine, isochavicine and chavicine, q.v.: R. De Cleyn, M. Verzele, Bull. Soc. Chim. Belg. 84, 435 (1975). Synthesis of isomers: R. Grewe et al., Ber. 103, 3752 (1970); of piperine and isochavicine: S. Tsuboi et al., Tetrahedron Lett. 1979, 1043. Stereoselective synthesis of piperine: R. A. Olsen, G. O. Spessard, J. Agric. Food Chem. 29, 942 (1981). More toxic to houseflies than pyrethrum: Harvill et al., Contrib. Boyce Thompson Inst. 13, 87 (1943).

Chemical structure

Properties

Monoclinic prisms from alcohol, mp 130°. Tasteless at first, but burning aftertaste. Neutral to litmus. pK (18°): 12.22. Almost insol in water (40 mg/liter at 18°), in petr ether. One gram dissolves in 15 ml alcohol, 1.7 ml chloroform, 36 ml ether. Sol in benzene, acetic acid.

Derivative

(E,Z)-Form.

Nomenclature

Isochavicine.

Properties

Crystals from chloroform + hexane, mp 89° (Grewe), 103° (De Cleyn). uv max (methanol): 333 nm (ε 16300).

Derivative

(Z,E)-Form.

Nomenclature

Isopiperine.

Properties

Crystals from chloroform + hexane, mp 110° (Grewe), 86° (De Cleyn). uv max (methanol): 332 nm (ε 21800).

Use

To impart pungent taste to brandy. As insecticide.