Piperine

Beige solid

Fixed

127-130 ° C

Poorly in water (40 mg · l-1, 18 ° C)

Attention

• 514 mg · kg -1 ( LD50, rat, oral)
• 330 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Piperine (1- piperoylpiperidine ) is a piperidine alkaloid and also belongs to the group of the amide alkaloids, as it is the amide of piperinic and piperidine. It is a colorless to pale yellow solid with a monoclinic prismatic crystal structure. Piperine was first isolated in 1819 by Hans Christian Oersted.

Occurrence and synthesis

Piperine is the main alkaloid of black pepper ( Piper nigrum ) and the support of a hot pepper taste. It is found to be 5-9 percent in the black pepper, also in white pepper, long pepper in, and to 0.4 percent in cubeb pepper.

Piperine can be synthetically prepared from piperidine and piperinic, but can also be extracted with ethanol and then crystallized from black pepper.

Properties

By alcoholic caustic potash solution, piperine absorption of water can split into piperidine and piperinic.

Since by acid catalysis (including the stomach) also Formaldehyde can be released, it can be harmful in large quantities.

The pungent taste of piperine is linked to the trans-trans - position ( E, E ) of the two double bonds; under the influence of light form no longer pungent isomers with Z, Z - ( Chavicin, cis -cis), Z, E ( Isopiperin, cis- trans) and E, Z - structure ( Isochavicin, trans-cis isomer). This leads to the loss of flavor of the spice.

Pharmacology

Piperine stimulates, like all sharp materials, metabolism and secretion ( saliva, digestive juices ) and has an antimicrobial effect. Occasionally, it is therefore taken to support a juice fast.

There is evidence that piperine can be used as bioenhancers increase the bioavailability of other substances ( avoiding the first-pass effect, increased resorption in the gastro -intestinal tract ). For this reason, it is increasingly being used in bodybuilding and weight training as a dietary supplement. Therefore, the pharmaceutical industry is researching piperine.