Piperine
Title: Piperine
CAS Registry Number: 94-62-2
CAS Name: 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
Additional Names: (E,E)-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: 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).
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.
Melting point: mp 130°
pKa: pK (18°): 12.22
 
Derivative Type: (E,Z)-Form
Additional Names: Isochavicine
Properties: Crystals from chloroform + hexane, mp 89° (Grewe), 103° (De Cleyn). uv max (methanol): 333 nm (e 16300).
Melting point: mp 89° (Grewe), 103° (De Cleyn)
Absorption maximum: uv max (methanol): 333 nm (e 16300)
 
Derivative Type: (Z,E)-Form
Additional Names: Isopiperine
Properties: Crystals from chloroform + hexane, mp 110° (Grewe), 86° (De Cleyn). uv max (methanol): 332 nm (e 21800).
Melting point: mp 110° (Grewe), 86° (De Cleyn)
Absorption maximum: uv max (methanol): 332 nm (e 21800)
 
Use: To impart pungent taste to brandy. As insecticide.

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