Here is an alternative method of extracting piperine.
They can never take away Piperine and therefore Piperonal.
foxy
Solubilized oleoresin black pepper, method of making same, and method of adding same to chewing gumPatent US5087458
Oleoresin black pepper is an extract of pepper produced by extracting piperine, volatile oils and fixed oils from dried pepper pods by using a solvent, such as ethylene dichloride or acetone. After extraction, the solvent is removed, as by distillation, and there remains an extract of pepper known as oleoresin black pepper. The oleoresin black pepper is an unstable paste-like composition which, upon standing, separates into two phases. As a result of its instability, oleoresin black pepper is difficult to utilize in the manufacture of compositions that require its presence. By solubilizing the oleoresin black pepper into a stable, free-flowing, liquid oleoresin composition, the oleoresin black pepper becomes much easier to handle when used in various manufacturing processes. Unfortunately, oleoresin black pepper is very difficult to solubilize. The only solvent available for solubilizing oleoresin black pepper, prior to the discovery of the present invention, was benzyl alcohol. See U.S. Pat. No. 4,409,257.
Use of piperine as a bioavailability enhancerPatent US5744161
Example 14
A preparation obtained in a unique manufacturing process.
Commercially available Black pepper oleoresin or Long pepper oleoresin is used as the source of piperine. Ground up Black pepper or Long pepper can also be used.
To a mixture of butanol and hexane (35 liters), 35 kg Black pepper oleoresin is added and heated to 40.degree. C. The mixture is then cooled and filtered. The precipitate is washed with Butanol/hexane mixture to obtain crude piperine.
The crude piperine is dissolved in methanol at 60.degree. C. and treated with alumina and charcoal by stirring. It is then filtered and concentrated under vacuum to obtain a powder.
Bioperine.RTM.
Material thus prepared has the following specifications: Color: Pale yellow crystalline powder
Melting range: 128 degrees-131 degrees Celsius
Assay: min. 98% pure piperine (by HPLC)
Process for making high purity piperine for nutritional usePatent US6054585
Example
A process to recover piperine from resin of black pepper.
A reaction vessel was charged with 0.9 kg of urea, 3.7 kg of ethanol or 2.7 kg of methanol and 0.3 kg of the resin of black pepper to form a mixture. The mixture was refluxed for approximately one hour. The refluxed mixture was cooled overnight to a temperature of 0.degree. to 5.degree. C. The cooled mixture was then filtered to remove solids (e.g. wax, urea, fatty acids). The filtrate was then concentrated to obtain 180 g of piperine and some unreacted urea. The 180 g of piperine was recrystallized by adding ethanol. The piperine crystals were collected by filtration and dried to yield approximately 75 g of 98% pure piperine.
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Isolation of Natural Piperine (I)
Grind fresh peppercorns (25 g) to a fine powder, place in a Soxhlet thimble, and extract with
ethanol (100 mL) for 90 minutes. Cool the resulting solution, filter if necessary, and concentrate on
the rotary evaporator. Keep the water bath below 60 °C during the concentration. Dissolve the
residue in 10 % alcoholic potassium hydroxide (25 mL). Decant the solution if any residue re-
mains. Cool the solution in an ice bath, and add water dropwise (about 30 ml will be required) to
precipitate the piperine. Collect the piperine on a sintered glass funnel, and dry it on the vacuum
pump. If time allows, a recrystallization from acetone:hexanes (3:2) will produce cleaner material.
Record the mp, ir and 1 H nmr spectrum of piperine.
http://www.chemistry.uvic.ca/chem465-66/465e03piperine.pdf
Piperine Home Page
http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_home_page.htm