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1 Isolation of Piperine

((2E, 4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one)

1.1 Introduction
Pepper contains about 15 alkaloids whereas piperine is the main alkaloid in such fruits of black pepper containing about 90%. It is responsible for the hot taste and his name remains from the heterocyclic compound piperidine. It was first isolated in the 19th century. [1]

1.2 Structure
O O H H H N O H

1.3 Method Powdered black pepper was placed in the extraction thimble of a soxhlet apparatus and extracted with chloroform for two hours to obtain the piperine. Afterwards the solvent is removed in vacuo and 20 ml ethanolic potassium hydroxide solution was added with stirring. After filtering the mixture, the filtrate was allowed to stand overnight in the refrigerator. In consequence of no crystallization 4-5 ml water was added (addition of a small portion of water is a very important hint!) and the solution was allowed to stand in the refrigerator once again. Later the risen crystals were separated from solution by filtration. Then, the crystals (500 mg) were recrystallized from 10 ml cyclohexane/ Toluol (4:1 v/v). By having a look on the TLC some isomers were detected, so that 150 mg crystals were subjected to column chromatography with an eluent of toluene/ethyl acetate (2:1 v/v). After working up the fractions the piperine was obtained in form of shiny yellow crystals. Note (from D. Sicker): Crude piperine can also be recrystallized from cyclohexane alone, you have to take ca. 50 mL of cyclohexane for ca. 350 mg of crude piperine and reflux it for a few minutes. The only thing to mention is that you should not cool it in the refrigerator or in ice because it becomes a solid a 7 C.

Yield: Melting Point:

100 mg (0.35 mmol, 0.4 %) 124 128 C (toluene/ethyl acetate) (Literature: 127 129 C)[4]

Rf- value =

0,50 (toluene/ethyl acetate 2:1 v/v)

Spectroscopic data: [1]


O 7'' 2'' 1'' O 4'' 5'' 6''
3'' 4' 5'

H
3 4 5 2

H
1 1'

2' 3'

N
6

H O

Fig. 1: Structural formula of piperine


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H-NMR (400MHz, CDCl3): [ppm] = 1.59 (m, 4H, 3+5), 1.64 (m, 2H, 4), 3.55 (d, 4H, 2+6), 5.95 (s, 2H, 7), 6.44 (d, 1H, 2), 6.74 (m, 3H, 3, 4, 5), 6.89 (d, 1H, 4), 6.97 (s, 1H, 6), 7.40 (qd, 1H, 3)

1.4 Discussion
The yield of the piperine isolation from black pepper was not satisfying, because it depends on the charge of the pepper and the quality, so that the amount of piperine can be very different. Never the less the 1H-NMR shows that the piperine is clean at least. Compared to the
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H-NMR of the pure piperine, the signals were exact the same. I can say that the

isolation of the natural product was successful although it is a difficult one.

1.5 References
[1] S. Berger, D. Sicker, Classics in Spectroscopy. Isolation and Structure Elucidation of Natural Products 1st ed., WILEY-VCH Verlag & Co. KGaA, Weinheim, 2009, 53 Wikipedia: http://de.wikipedia.org/wiki/Piperin