{"id":729,"date":"2011-01-24T16:47:00","date_gmt":"2011-01-24T16:47:00","guid":{"rendered":"https:\/\/psiconautica.org\/wordpress\/?p=729"},"modified":"2022-12-23T11:20:49","modified_gmt":"2022-12-23T11:20:49","slug":"piperine-from-pepper","status":"publish","type":"post","link":"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/piperine-from-pepper\/","title":{"rendered":"Piperine from pepper"},"content":{"rendered":"<h3>Piperine from pepper by 3base<\/h3>\n<p>isolation of piperine (black pepper, EtOH, KOH)<br \/>\nisolation of piperine from black pepper (black pepper, EtOH, KOH, soxhlet)<br \/>\nisolation of piperine from black pepper (black pepper, IPA, CaCO3)<br \/>\nisolation of piperine from black pepper (black pepper, CH2Cl2)<br \/>\nisolation of natural piperine (pepper, EtOH, KOH, soxhlet)<br \/>\nextraction and isolation (piper nigrum, EtOH)<br \/>\npiperine and piperiline extraction (black pepper, EtOH, soxhlet, hexane:ether column)<br \/>\npiperine form piper longum (piper longum, CH2Cl2:MeOH, PE:EtOAc column)<\/p>\n<p>oleoresin of pepper<br \/>\npiperine from resin of black pepper (black pepper resin, EtOH, urea)<br \/>\nsource of piperine (black\/long pepper\/oleoresin, BuOH, hexane, alumina, charcoal)<br \/>\noleoresin of pepper [03] (black pepper, ether)<\/p>\n<p>further recipes and references<\/p>\n<h3>isolation of piperine<\/h3>\n<p>place 15g (1) of &#8230; ground black pepper in a 250mL round-bottomed flask,<br \/>\nadd 150mL of 95% ethanol and 5 boiling chips (2), and heat at reflux for 2h.<br \/>\nfilter the mixture by suction filtration and then concentrate the filtrate to a<br \/>\nvolume of 10-15mL by simple distillation or by use of a rotary evaporator.<br \/>\nto 10mL of a 10% solution of KOH in 95% ethanol contained ina 125mL<br \/>\nerlenmeyer flask add the concentrated pepper extract. heat the resulting<br \/>\nsolution and add water dropwise. a yellow precipitate forms. add water<br \/>\nuntil no more solid appears to form and then allow the mixture to stand at<br \/>\nleast overnight (3). collect the solid by suction filtration and recrystallize it<br \/>\nwith 10-20mL of acetone (4).<\/p>\n<p>(1) this extraction may be scaled up to twice the amounts specified without<br \/>\ndifficultiy. if a soxhlet extractor is available, this would be an apparatus superior<br \/>\nto a standard reflux setup.<\/p>\n<p>(2) boiling chips are necessary to prevent serious bumping.<\/p>\n<p>(3) it is best to allow piperine to completely precipitate out by allowing the<br \/>\nmixture to stand until the next laboratory period.<\/p>\n<p>(4) in our hands ca. 0.6g of piperine, mp 127-128\u00b0C, was collected upon<br \/>\nrecrystallization.<\/p>\n<p>[05, page 527-528]<\/p>\n<h3>isolation of piperine from black pepper<\/h3>\n<p>procedure<br \/>\n10g black pepper is ground to a fine powder and extracted with 150mL 95%<br \/>\nethanol in a soxhlet extractor for 2h. the solution is filtered and concentrated in<br \/>\nvacuo on a water bath at 60\u00b0C. 10mL 10% alcoholic KOH solution is added &#8230;<br \/>\nand after a while decanted from the insoluble residue. the alcoholic solution is<br \/>\nleft overnight, whereupon 0.3g yellow needles are deposited, mp 125-126\u00b0C.<\/p>\n<p>TLC of black pepper extract<br \/>\nthe crude extract is spotted on a thin-layer plate (silica gel GF254)<br \/>\nand developed with benzene:EtOAc 2:1.<br \/>\ndetection:<br \/>\n(1) UV365 shows blue fluorescence of piperine<br \/>\n(2) spraying with anisaldehyde-sulfric acid reagent, prepared by mixing 0.5mL<br \/>\nanisaldehyde with 10mL glacial acetic acid, 85mL MeOH, and 5mL concentrated<br \/>\nsulfric acid. this solution is sprayed on the plate, which is then heated at 110\u00b0C<br \/>\nfor 10min. piperine appears as a yellow spot, Rf=0.25.<\/p>\n<p>[06, page 233-236]<\/p>\n<h3>isolation of piperine from black pepper<\/h3>\n<p>piperine, a very weakly basic substance, can be isolated from a variety of peppers<br \/>\nby extraction with alcohol. &#8230; piperine, along with a small amount of its Z,E isomer,<br \/>\naccounts for about 10% of the weight of black pepper.<\/p>\n<p>procedure<br \/>\nplace 15g of ground black pepper and 1g of powdered CaCO3 (1) in a 250mL<br \/>\nboiling flask, add 100mL of IPA, and, after fitting the flask with a reflux condenser,<br \/>\nboil the mixture for about 1h on the steam bath. at the end of the heating period,<br \/>\nfilter the mixture by gravity into a 125mL erlenmeyer flask, clean the 250mL<br \/>\nboiling flask, and return the filtrate to the boiling flask. fit the boiling flask with a<br \/>\ndistillation adapter and condenser, and boil off all but about 10mL of the IPA (2).<br \/>\ntransfer the residual solution from the boiling flask to a 25mL erlenmeyer flask,<br \/>\nand set the flask aside to cool for crystallization of piperine (3,4). collect the product<br \/>\nby suction filtration, using small portions of MeOH to rinse the flask and wash<br \/>\nthe product. yield: about 0.5g.<\/p>\n<p>(1) the addition of CaCO3 should prevent the extraction of acidic<br \/>\ncomponents of pepper<\/p>\n<p>(2) IPA boils at 80\u00b0C, only a little below the maximum temperature attainable on<br \/>\nthe steam bath. to make the distillation proceed quickly, clamp the boiling flask so<br \/>\nthat it is well down in the rings of the steam bath, and drape a towel over the flask<br \/>\nand the steam bath to make a tent that will hold steam around the top of the flask.<\/p>\n<p>(3) crystallization occurs slowly, and the flask must be allowed to stand for<br \/>\nat least 24h.<\/p>\n<p>(4) alternatively, add 25mL of water to the IPA solution of piperine, allow the mixture<br \/>\nto stand for at least 24h so that precipitation will be complete, collect the solid by<br \/>\nsucction filtration, and recrystallize it from either IPA or acetone.<\/p>\n<p>[04, page 340-341]<\/p>\n<h3>isolation of piperine from black pepper<\/h3>\n<p>add 5g of pure ground pepper and 10mL of CH2Cl2 to 50mL round-bottomed flask.<br \/>\nuse the round-rottomed flask as the basis for a reflux apparatus having a water-cooled<br \/>\ncondenser and heating mantle. heat the sample to reflux, and then maintain a gentle<br \/>\nreflux for 20min. after the required reflux period, lower the heating mantle and allow the<br \/>\nreflux apparatus to cool for 5min. suction filter the slurry with the aid of a 4.5cm buchner<br \/>\nfunnel, washing the pepper grounds once with 5mL of CH2Cl2. remove 2 or 3 drops of<br \/>\nthe extract and place it in a capped vial for use in the TLC analysis.<\/p>\n<p>trituration\/isolation<br \/>\ntransfer the extract obtained above to a clean 25mL round-bottomed flask and<br \/>\nconcentrate in vacuo. the resulting olive-brown, viscous oil should be cooled in an<br \/>\nice-bath and then 3mL of cold ether added to the oil while gently stirring for 3-4min.<br \/>\nsome piperine may percipitate at this point, but remove the solvent in vacuo anyway.<br \/>\nonce again coole the resulting oil in an ice-bath and then add 3mL of cold ether to the<br \/>\noil while gently stirring to promote the percipitation of piperine. allow the flask to cool<br \/>\nfor an additional 10min with occasional stirring. isolate the straw-yellow crystals of<br \/>\ncrude piperine by suction filtration with the aid of a 1.5cm hirsch funnel. wash the<br \/>\ncrystals twice with 2mL portions of cold ether. place a small portion of the filtrate in a<br \/>\ncapped vial for use in the TLC analysis.<\/p>\n<p>recrystallization<br \/>\nplace the crude piperine isolated above into a 13x100mm test tube and dissolve it in a<br \/>\nminimum amount of hot 3:2 acetone:hexane solution. once all the solid has dissolved,<br \/>\nallow the test tube to sit undisturbed for 15min at room temperature. rod-like, yellow<br \/>\ncrystals of piperine should be present. cool the solution for an additional 30min in an<br \/>\nice-bath before isolating the purified piperine by suction filtartion with the help of a 1.5cm<br \/>\nhirsch funnel. wash the crystals once with a 2mL portion of cold ether, allow them to air<br \/>\ndry for several minutes. typically, yields of approximately 2% or 100mg are obtained.<br \/>\nthe melting point of the purified piperine now can be determined and the identity of the<br \/>\nproduct confirmed by mixed melting point, TLC analysis, or spectral analysis.<\/p>\n<p>TLC analysis<br \/>\ntransfer a small portion of the purified crystals to a small vial and dissolve them in a<br \/>\ndrop or two of acetone. prepare a silica-gel TLC plate for the spotting of 4 samples<br \/>\n(kieselgel 60 F254 plates having a 0.2mm coating thickness are recomended).<br \/>\nwith the aid of a capillary, place a sample of the crude oil remaining from the extraction<br \/>\nprocedure, a sample of the filtrate from the trituration\/isolation procedure, the sample<br \/>\nprepared from the purified piperine, and a sample of a piperine standard on separate<br \/>\npoints of the thin-layer plate. develop the plate using 3:2 acetone:hexane.<br \/>\nvisualize under UV illumination and stain in an iodine chamber.<\/p>\n<p>[01]<\/p>\n<h3>isolation of natural piperine<\/h3>\n<p>grind 25g fresh peppercorns to a fine powder, place in a soxhlet thimble, and extract<br \/>\nwith 100mL ethanol for 90 minutes. cool the resulting solution, filter if necessary, and<br \/>\nconcentrate on the rotary evaporator. keep the water bath below 60\u00b0C during the<br \/>\nconcentration. dissolve the residue in 25mL 10% alcoholic KOH. decant the solution<br \/>\nif any residue remains. cool the solution in an ice bath, and add water dropwise<br \/>\n(about 30mL will be required) to precipitate the piperine. collect the piperine on a<br \/>\nsintered glass funnel, and dry it on the vacuum pump.<br \/>\n&#8230; recrystallization from acetone:hexane 3:2 will produce cleaner material.<\/p>\n<p>[14]<\/p>\n<h3><a name=\"isolation_extraction\"><\/a><br \/>\nextraction and isolation<\/h3>\n<p>10kg dried fruits of <em>p nigrum l<\/em> &#8230; were crushed and extracted 5x with EtOH at room<br \/>\ntemp. after removal of solvent in vacuo, the syrupy residue was left overnight at room<br \/>\ntemp. when a white crystallizate sept out, which was filtered. on recrystallization from<br \/>\nMeOH it formed 50.54g fine needles, mp 128-129\u00b0, and was identified as piperine.<\/p>\n<p>[19]<\/p>\n<h3>piperine and piperiline extraction<\/h3>\n<p>750g dry fruits of black pepper were ground and extracted with 2.5L ethanol, in a<br \/>\nsoxhlet apparatus for 72h. the extract was concentrated under reduced pressure<br \/>\nin a rotary evaporator to leave 8g of a dark brown oil. this material was fractionated<br \/>\non a silica gel column, eluting with hexane + diethyl ether (1 + 2 by volume).<br \/>\nthe fractions obtained were combined according to their similarities as analysed by<br \/>\nthin layer chromatography (TLC) and this led to the isolation of 2g piperine and 0.3g<br \/>\npiperiline. these compounds were recrystallised with a mixture of dichloromethane<br \/>\nand hexane and the physical and spectroscopic data obtained were in accordance<br \/>\nwith those reported in the literature.<\/p>\n<p>[09]<\/p>\n<h3>piperine form piper longum<\/h3>\n<p><em>p longum<\/em> &#8230; 500g dried fruits were powdered and extracted 120h with CH2Cl2:MeOH<br \/>\n1:1. the concentrated extract (1.45g) was chromatographed over silica gel, the column<br \/>\nbeing eluted with pet. ether and pet. ether-EtOAc mixture. the following compounds were<br \/>\neluted according to the increasing order of polarity: 120mg tridecyldihydro-<em>p<\/em>-coumarate,<br \/>\n126mg eicosanyl-(E)-<em>p<\/em>-coumarate, 132mg pellitorine, 67mg piperlongumine and 148mg<br \/>\npiperine.<\/p>\n<p>[35]<\/p>\n<h3>oleoresin of pepper<\/h3>\n<p>&#8230; black pepper &#8230; ground &#8230; berries must be extracted repeatedly(percolated) with<br \/>\nvolatile solvents: alcohol, acetone or ether. concentration of the solutions and removal<br \/>\nof the solvent in vacuo yields the socalled oleoresin of pepper.<br \/>\nquantitative composition of the oleoresin depends upon the solvent used. oleoresin<br \/>\nof pepper generally contains these compounds: 1.<em> piperine<\/em>, &#8230; 2.<em> chavicine<\/em>, &#8230; an<br \/>\nisomer of piperine &#8230; 3.<em> other piperidides<\/em>, &#8230; 4.<em> the volatile oil<\/em>, &#8230; 5.<em> a volatile alkaloid<\/em>,<br \/>\n&#8230; present in samll quantities only. 6.<em> resins<\/em>, not identified.<\/p>\n<p>[08, page 144]<\/p>\n<h3>process to recover piperine from resin of black pepper<\/h3>\n<p>a reaction vessel was charged with 0.9kg urea, 3.7kg ethanol (or 2.7kg methanol)<br \/>\nand 0.3kg of the resin of black pepper to form a mixture. the mixture was refluxed<br \/>\nfor approximately 1h. the refluxed mixture was cooled overnight to 0-5\u00b0C. the cooled<br \/>\nmixture was then filtered to remove solids (e.g wax, urea, fatty acids). the filtrate was<br \/>\nthen concentrated to obtain 180g of piperine and some unreacted urea. the 180g of<br \/>\npiperine was recrystallized by adding ethanol. the piperine crystals were collected<br \/>\nby filtration and dried to yield approximately 75g of 98% pure piperine.<\/p>\n<p>[12]<\/p>\n<h3>source of piperine<\/h3>\n<p>black pepper oleoresin or long pepper oleoresin is used as the source of piperine.<br \/>\nground up black pepper or long pepper can also be used<\/p>\n<p>to 35L buthanol\/hexane mixture, 35kg black pepper oleoresin is added and<br \/>\nheated to 40\u00b0C. the mixture is then cooled and filtered. the percipitate is washed<br \/>\nwith buthanol\/hexane mixture to obtain crude piperine. the crude piperine is<br \/>\ndissolved in ethanol at 60\u00b0C and treated with alumina and charcoal by stirring.<br \/>\nit is then filtered and concentrated under vacuum to obtain a pale yellow crystalline<br \/>\npowder, melting range: 128-131\u00b0C, min.98% pure piperine (by HPLC).<\/p>\n<p>[13]<\/p>\n<h3>further recipes and references<\/h3>\n<p>with EtOH [26, (1)]<\/p>\n<p>with MeOH [27]<\/p>\n<p>with EtOAc: recipe 1, recipe 2<\/p>\n<p>with CHCl2: recipe 1 [10], recipe 2<\/p>\n<p>with acetone: [hive post 282850 on 2002-03-15 by Antoncho]<\/p>\n<p>microwave-assisted extraction of piperine from piper nigrum [15]<\/p>\n<p>extraction of piperine from piper nigrum (black pepper)<br \/>\nby hydrotropic solubilization [31]<\/p>\n<p>process for extraction of piperine from piper species [07]<\/p>\n<p>extraction and description of the piperines in pepper [16]<\/p>\n<p>isolation of piperine from black pepper<br \/>\n[http:\/\/www.wiu.edu\/users\/mftkv\/Chem332\/Experiment3.html]<\/p>\n<p>&#8230; extracted ground black pepper with acetone &#8230;<br \/>\nagricult food chem, 1981 29, 115; su, horvat<br \/>\n(mentioned in [21])<\/p>\n<p>&#8230; piper nigrum fruit extract and its main alkaloid, piperine [17]<\/p>\n<p>&#8230; pepper raw spice, oleoresins, and soluble seasonings.<br \/>\npiperine is extracted into ethylene dichloride &#8230; [11]<\/p>\n<p>&#8230; pepper or piper longum &#8230; is extracted &#8230; [34]<\/p>\n<p>process for preparing piperine [02]<\/p>\n<p>immersing extraction of pepper [32]<\/p>\n<p>CO2 extraction, up to 9.2% piperine from black pepper(madagascar) [23]<\/p>\n<p>liquid CO2 extraction of piperine &#8230; of pepper [33]<\/p>\n<h2>References<\/h2>\n<p>[hive]<br \/>\n<a href=\"http:\/\/www.the-hive.ws\/\" target=\"_blank\" rel=\"noopener noreferrer\">http:\/\/www.the-hive.ws\/<\/a><\/p>\n<p>[pubmed]<br \/>\n<a href=\"http:\/\/www.ncbi.nlm.nih.gov\/entrez\/query.fcgi?db=PubMed\" target=\"_blank\" rel=\"noopener noreferrer\">http:\/\/www.ncbi.nlm.nih.gov\/entrez\/query.fcgi?db=PubMed<\/a><\/p>\n<p>[01]<br \/>\njournal of chemical education 1993 70(7): 598-599<br \/>\n<strong>\u00abisolation of piperine from black pepper\u00bb<\/strong><br \/>\nwilliam w epstein, david f netz, jimy l seidel<\/p>\n<p>[02]<br \/>\npatent <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=CN1294127&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">CN1294127<\/a>, 2001-05-09 (chinese)<br \/>\n<strong>\u00abprocess for preparing piperine\u00bb<\/strong><br \/>\nxiaoming lin, zaifeng shi, zhenfan sun<br \/>\n(Lutianyuan Hi-Tech Development Co., Ltd., Hainan, Peop. Rep. China)<br \/>\nFaming Zhuanli Shenqing Gongkai Shuomingshu<br \/>\n<strong>abstract (from esp@cenet):<\/strong> a process for preparing piperine includes<br \/>\nimmersing extraction of pepper is mixed organic solvent, distilling to<br \/>\nseparate out organic solvent to obtain liquid mixture of pepper oil resin<br \/>\nand piperine, cooling to separate out the pepper oil resin, and further<br \/>\npurifying. Its advantages are simple process, high extraction rate and<br \/>\nseparation effect, and high purity.<br \/>\n<strong>abstract (from CAS):<\/strong> the process comprises extg. pepper with mixed<br \/>\nsolvent at 25-40\u00b0 for 1-6 h, filtering, concg., crystg., and recrystg. with<br \/>\ndichloroethylene or Et acetate. the mixed solvent is ethanol, methanol,<br \/>\nacetone, Et ether, Et acetate, dichloromethane, benzene, and\/or chloroform.<br \/>\n<strong>keywords (from CAS):<\/strong> piperine isolation pepper<\/p>\n<p>[03]<br \/>\n<a href=\"http:\/\/www.ibiblio.org\/herbmed\/eclectic\/kings\/main.html\" target=\"_blank\" rel=\"noopener noreferrer\">king&#8217;s american dispensatory<\/a> 1898<br \/>\nm d harvey wickes felter, phr m ph d john uri lloyd<\/p>\n<p>[04]<br \/>\n<strong>\u00abtechniques and experiments for organic chemistry\u00bb <\/strong>6.edition 1998<br \/>\naddison ault (cornell college); universityscience books, susalito, california<br \/>\nISBN 0-935702-76-8<\/p>\n<p>[05]<br \/>\n<strong>\u00ablaboratory experiments in organic chemistry\u00bb<\/strong> 3.edition 1979<br \/>\njerry r. mohrig, douglas c. neckers<br \/>\nd. van nostrand company, new york<br \/>\nISBN 0-442-25471-7<\/p>\n<p>[06]<br \/>\n<strong>\u00abnatural products &#8211; a laboratory guide\u00bb<\/strong> 2.edition 1991<br \/>\nraphael ikan; academic press, inc; ISBN 0-12-370551-7<\/p>\n<p>[07]<br \/>\npatent US6365601, 2002-04-02<br \/>\n<strong>\u00abprocess for extraction of piperine from piper species\u00bb<\/strong><br \/>\nRAMAN GIRIJA (IN); GAIKAR VILAS GAJANAN (IN)<br \/>\nCOUNCIL SCIENT IND RES (IN)<br \/>\n<strong>abstract:<\/strong> the present invention relates to a process for extraction<br \/>\nof piperine of formula I from the fruits of piper species, comprising<br \/>\nthe steps of:contacting the fruit of piper species with aqueous<br \/>\nhydrotrope solution at a temperature in the range of 0-100 C. and<br \/>\nseparating the solution from the solid residue by known methods, and<br \/>\nrecovering piperine from the solution by known methods.<\/p>\n<p>[08]<br \/>\n<strong>\u00abthe essential oils\u00bb<\/strong> volume five 1952, ernest guenther<br \/>\nd van nostrand company, toronto &#8211; new york &#8211; london<\/p>\n<p>[09]<br \/>\n<a href=\"pest.manag.sci_2000.56.2_168-174.pdf\" target=\"_blank\" rel=\"noopener noreferrer\">pest management science 2000 56(2): 168-174<\/a><br \/>\n<strong>\u00absynthesis and insecticidal activity of new amide derivatives of piperine\u00bb<\/strong><br \/>\nvanderl\u00facia fde paula, luiz c de a barbosa, ant\u00f4nio j demuner,<br \/>\ndorila pil\u00f3-veloso, marcelo c pican\u00e7o<br \/>\n<strong>abstract<\/strong><strong>:<\/strong> the natural lipophilic amides piperine and piperiline were isolated<br \/>\nfrom piper nigrum l (piperaceae). piperine was hydrolysed into piperic acid<br \/>\n(85% yield) which was converted into 16 amides (28-89% yield). the contact<br \/>\ntoxicity of all synthetic amides, and also that of piperine and piperiline, at the<br \/>\ndose 10 \u00b5g per insect, was evaluated for the brazilian economically important<br \/>\ninsects ascia monuste orseis latr, acanthoscelides obtectus say, brevicoryne<br \/>\nbrassicae l, protopolybia exigua de saus and cornitermes cumulans kollar.<br \/>\nthe results demontrated that the insects have different sensivities to the various<br \/>\namides, with mortality ranging from 0 to 97.5% according to the compound<br \/>\nand insect species.<\/p>\n<p>[10]<br \/>\n<a href=\"http:\/\/www.uni-bayreuth.de\/departments\/oc1\/teaching\/phbcan99.rtf\" target=\"_blank\" rel=\"noopener noreferrer\">phbcan99.rtf<\/a> from <a href=\"http:\/\/www.uni-bayreuth.de\/departments\/oc1\/teaching\/\" target=\"_blank\" rel=\"noopener noreferrer\">http:\/\/www.uni-bayreuth.de\/departments\/oc1\/teaching\/<\/a><br \/>\n<strong>\u00abisolierung von piperin aus schwarzem pfeffer und abbau zur piperinsaeure\u00bb<\/strong><br \/>\nANALYTISCHES PRAKTIKUM fuer Biochemiker (Stand: September 1999), page 16-18<\/p>\n<p>[11]<br \/>\nj assoc off anal chem 1987 70(1): 112-3<br \/>\n<strong>\u00abUV spectrophotometric determination of piperine in pepper preparations:<br \/>\ncollaborative study.\u00bb<\/strong><br \/>\nt lupina, h cripps<br \/>\n<strong>abstract<\/strong><strong>:<\/strong> eight collaborating laboratories performed replicate analyses for piperine<br \/>\non 5 samples representing pepper raw spice, oleoresins, and soluble seasonings.<br \/>\npiperine is extracted into ethylene dichloride and measured at maximal<br \/>\nabsorbance 342-345 nm with a UV light source. piperine content is calculated<br \/>\nusing an absorbance factor derived from piperine. Intralaboratory coefficients<br \/>\nof variation (CVo) ranged from 0.5 to 3.1%; interlaboratory coefficients of<br \/>\nvariation (CVx) ranged from 3.0 to 5.8%. the method has been adopted as an<br \/>\nofficial method of the american spice trade association and as an official first<br \/>\naction method by AOAC.<br \/>\n[<a href=\"#pubmed\">pubmed<\/a>, PMID: <a href=\"http:\/\/www.ncbi.nlm.nih.gov\/htbin-post\/Entrez\/query?db=m&amp;form=6&amp;Dopt=r&amp;uid=3558260\" target=\"_blank\" rel=\"noopener noreferrer\">3558260<\/a>]<\/p>\n<p>[12]<br \/>\npatent <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=US6054585&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">US6054585<\/a>, 2000-04-25<br \/>\n<strong>\u00abprocess for making high purity piperine for nutritional use\u00bb<\/strong><br \/>\nmuhammed majeed, vladimir badmaev; sabinsa corp<br \/>\n<strong>abstract<\/strong>: the present invention relates to a process of making high purity<br \/>\npiperine for nutritional and nutraceutical application. this process recovers<br \/>\npiperine from piperine-containing oleoresin by using isourea, urea or a<br \/>\nurea derivative to remove organic matter other than piperine from the<br \/>\noleoresin. preferrably, the process recovers piperine from oleoresin of fruit<br \/>\nof piper nigrum or piper longum. more preferably, the process recovers<br \/>\npiperine from oleoresin of fruit of piper nigrum, i.e. black pepper.<\/p>\n<p>[13]<br \/>\npatents US5744161, <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=US6054585&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">US6054585<\/a>, US5972382, <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=US5536506&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">US5536506<\/a><\/p>\n<p>[14]<br \/>\nhttp:\/\/www.chemistry.uvic.ca\/chem465-66\/<a href=\"465e03piperine.pdf\" target=\"_blank\" rel=\"noopener noreferrer\">465e03piperine.pdf<\/a> from<br \/>\n<a href=\"http:\/\/www.chemistry.uvic.ca\/chem465-66\/465organic.htm\" target=\"_blank\" rel=\"noopener noreferrer\">http:\/\/www.chemistry.uvic.ca\/chem465-66\/465organic.htm<\/a><\/p>\n<p>[15]<br \/>\n<a href=\"ind.eng.chem.res_2002.41.10_2521-2528.pdf\" target=\"_blank\" rel=\"noopener noreferrer\">ind eng chem res 2002 41(10): 2521-2528<\/a><br \/>\n<strong>\u00abmicrowave-assisted extraction of piperine from piper nigrum\u00bb<\/strong><br \/>\ngirija raman, vilas g gaikar<br \/>\n<strong>abstract<\/strong><strong>:<\/strong> a novel microwave-assisted technique (MAE) for the extraction of<br \/>\npiperine from coarsely powdered black pepper (Piper nigrum) was studied.<br \/>\nthe parameters such as nature of the solvent, microwave energy input, and<br \/>\nsolid loading were optimized. the mechanism of the enhancement of extraction<br \/>\nrates was investigated by microscopic studies of the irradiated material.<br \/>\nstudies have revealed that dielectric heating of the polar cellular matrix resulted<br \/>\nin remarkable swelling and coalescence of the oil cells and other constituents.<br \/>\nthe resulting pressure, built-up within the cell, breaks open the cell, releasing<br \/>\nthe constituents and providing easy access for solvent penetration and<br \/>\nsubsequent solubilization of piperine and other substances. because the cell wall<br \/>\nis mainly composed of slightly ionic cellulose, there is a marked increase in the<br \/>\ndielectric heating rates. rapid degradation of the cellulosic cell wall occurs,<br \/>\nthereby further increasing the permeability of the wall toward solvent penetration.<br \/>\nselective extraction of piperine in nonpolar solvents to the extent of 94% with a<br \/>\npurity of 85% has been achieved. the MAE procedure is simple, rapid, and reliable.<\/p>\n<p>[16]<br \/>\nbull soc chim 1877 27(2): 290<br \/>\n<strong>\u00abthe extraction and description of the piperines in pepper\u00bb<\/strong><br \/>\np caseneuve, o caillol<\/p>\n<p>[17]<br \/>\nplanta medica 1999 65: 600-3<br \/>\n<strong>\u00abstimulation of mouse melanocyte proliferation by<br \/>\npiper nigrum fruit extract and its main alkaloid, piperine\u00bb<\/strong><br \/>\nzhixiu lin, j r s hoult, dorothy c bennett, amala raman<br \/>\n<strong>abstract:<\/strong> during a herbal screening programme to find potential repigmenting agents<br \/>\nfor the treatment of vitiligo, piper nigrum l. fruit (black pepper) extract was found to<br \/>\npossess growth-stimulatory activity towards cultured melanocytes. its aqueous extract<br \/>\nat 0.1mg\/ml was observed to cause nearly 300 % stimulation of the growth of a cultured<br \/>\nmouse melanocyte line, melan-a, in 8 days (p &lt; 0.01). piperine (1-piperoylpiperidine),<br \/>\nthe main alkaloid from piper nigrum fruit, also significantly stimulated melan-a cell growth.<br \/>\nboth piper nigrum extract and piperine induced morphological alterations in melan-a cells,<br \/>\nwith more and longer dendrites observed. the augmentation of growth by piperine was<br \/>\neffectively inhibited by RO-31-8220, a selective protein kinase C (PKC) inhibitor,<br \/>\nsuggesting that PKC signalling is involved in its activity. this is the first full report on such<br \/>\nan activity of black pepper and piperine.<\/p>\n<p>[19]<br \/>\n<a href=\"phytochemistry_1997.45.8_1617-1619.pdf\" target=\"_blank\" rel=\"noopener noreferrer\">phytochemistry 1997 45(8): 1617-1619<\/a><br \/>\n<strong>\u00aban amide from fruits of piper nigrum\u00bb<\/strong><br \/>\nbina s siddiqui, sabira begum, tahsin gulzar, farhat noor, fatima noor<br \/>\n<strong>abstract:<\/strong> a new amide, N-isobutyl amide of octadeca-trans-2-cis-4-dienoic acid<br \/>\nhas been isolated from the dried and crushed fruits of <em>piper nigrum<\/em>, along with the<br \/>\nknown alkaloid, piperine. complete assignments of the protons and carbons of the<br \/>\nnew amide and piperine have been made based on 2D NMR studies.<\/p>\n<p>[21]<br \/>\npatent <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=US4820517&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">US4820517<\/a>, 1989-04-11<br \/>\n<strong>\u00abprocess for obtaining a pepper extract with insecticidal activity\u00bb<\/strong><br \/>\nHANS PFEIFFER, MANFRED BIERMANN, PETER SCHROEDER,<br \/>\nGERD GOEBEL, ANNEMARIE MUELLER; HENKEL KGAA<br \/>\n<strong>abstract:<\/strong> PCT No. PCT\/EP85\/00333 Sec. 371 Date Jul. 24, 1986 Sec. 102(e) Date<br \/>\nJul. 24, 1986 PCT Filed Jul. 6, 1985 PCT Pub. No. WO86\/01981 PCT Pub. Date Apr.<br \/>\n10, 1986.An insecticidally active fraction is obtained from black pepper by a process<br \/>\ncomprising the following steps: (a) extraction of black pepper in ground form with CO2<br \/>\nat 30 to 70\u00b0C and 150 to 500 bar; (b) removal of sharp tasting fractions therein in a first<br \/>\nexpansion step at 25 to 35\u00b0C and 70 to 150 bar; (c) removal of an oily fraction containing<br \/>\nthe insecticidally active components as well as most of the essential oils in a second<br \/>\nexpansion step at 15 to 30\u00b0C and 40 to 70 bar; (d) removal of essential oils by steam<br \/>\ndistillation, and if desired; (e) hydrogenation of the insecticidally active components.<\/p>\n<p>[23]<br \/>\npatent EP0023680, 1981-02-11<br \/>\n<strong>\u00abprocess for the production of spice extracts\u00bb<\/strong><br \/>\nNORBERT BEHR, HENK VAN DER MEI, WOLFGANG SIRTL, DR HARALD<br \/>\nSCHNEGELBERGER, DR OTHMAR VON ETTINGSHAUSEN; HENKEL KGAA<br \/>\n<strong>abstract<\/strong><strong>:<\/strong> 1. aprocess for the production of spice extracts by extraction with a<br \/>\nphysiologically acceptable gas as a solvent in two stages, characterised in that the<br \/>\nethereal oils acting as odour component are removed from the spices in the first stage<br \/>\nusing a liquid gas of which the temperature is in the subcritical range and the pressure<br \/>\nin the supercritical range whilst the flavour components are removed in the second<br \/>\nstage using the same gas of which the temperature and pressure are both in the<br \/>\nsupercritical range, the extracts are separated off from the solutions obtained by<br \/>\nchanging the pressure and\/or temperature and optionally mixed with one another.<\/p>\n<p>[26]<br \/>\n<a href=\"recipe_piperine_piperic_acid.txt\" target=\"_blank\" rel=\"noopener noreferrer\">(1) piperine from black pepper (2) hydrolysis of piperine to piperic acid<\/a><br \/>\nhttp:\/\/www.rhodium.ws\/chemistry\/piperine.txt<\/p>\n<p>[27]<br \/>\n<a href=\"recipe_piperine_piperonal.txt\" target=\"_blank\" rel=\"noopener noreferrer\">\u00abpiperine to piperonal procedure\u00bb<\/a>, the cook<br \/>\nhttp:\/\/www.rhodium.ws\/chemistry\/piperine.txt<\/p>\n<p>[31]<br \/>\n<a href=\"ind.eng.chem.res_2002.41_2966-2976.pdf\" target=\"_blank\" rel=\"noopener noreferrer\">ind eng chem res 2002 41(12): 2966-2976<\/a><br \/>\n<strong>\u00abextraction of piperine from piper nigrum (black pepper)<br \/>\nby hydrotropic solubilization\u00bb<\/strong><br \/>\ngirija raman, vilas g gaikar<br \/>\n<strong>abstract:<\/strong> hydrotropes, such as sodium alkyl benzene sulfonates and sodium butyl<br \/>\nmonoglycol sulfate, were used for the selective extraction of piperine by cell<br \/>\npermeabilization of piper nigrum fruits. penetration of the hydrotrope molecules into<br \/>\nthe cellular structures and subsequent cell permeabilization were hypothesized to<br \/>\nexplain the enhanced extraction rates of aqueous hydrotrope solutions. hydrotrope<br \/>\nmolecules, after adsorption on a cell wall, cause disorder in its structure and in the<br \/>\nbilayered cell membrane to facilitate the rapid extraction of piperine. the hydrotrope<br \/>\nsolution showed selective and rapid extraction of piperine from black pepper.<br \/>\nthe recovered piperine was ~90% pure and substantially free from oleoresins. the<br \/>\ntype and nature of the hydrotrope, the hydrotrope concentration, the temperature,<br \/>\nand the particle size all had significant effects on the extraction process.<\/p>\n<p>[32]<br \/>\npatent <a href=\"http:\/\/l2.espacenet.com\/dips\/viewer?PN=CN1294127&amp;CY=ep&amp;LG=en&amp;DB=EPD\" target=\"_blank\" rel=\"noopener noreferrer\">CN1294127<\/a>, 2001-05-09<br \/>\n<strong>\u00abprocess for preparing piperine\u00bb<\/strong><br \/>\nSHI ZAIFENG, SUN ZHENFAN, LIN XIAOMING; LUTIANYUAN HI TECH DEV CO LTD<br \/>\n<strong>abstract:<\/strong> A process for preparing piperine includes immersing extraction of pepper is<br \/>\nmixed organic solvent, distilling to separate out organic solvent to obtain liquid mixture<br \/>\nof pepper oil resin and piperine, cooling to separate out the pepper oil resin, and further<br \/>\npurifying. Its advantages are simple process, high extraction rate and separation effect,<br \/>\nand high purity.<\/p>\n<p>[33]<br \/>\npatent US4985265, 1991-01-15<br \/>\n<strong>\u00abprocess for extraction of spices\u00bb<\/strong><br \/>\nDUBOC SORAYA, RENON HENRI, LAUGIER SERGE, MIZANDJIAN JEAN-LUC,<br \/>\nPEAN JEAN-LOUIS; L AIR LIQUIDE SOCIETY ANONYME<br \/>\n<strong>abstract:<\/strong> a process for extracting spices in liquid carbon dioxide in the presence<br \/>\nof an alimentarily acceptable cosolvent which does not degrade the flavors of the<br \/>\nspices. the process is particularly applicable to the extraction of piperine and<br \/>\naromatic compounds of pepper.<\/p>\n<p>[34]<br \/>\npatent CN1298936, 2001-06-13<br \/>\n<strong>\u00abprocess for preparing health-care peperic acid wine\u00bb<\/strong>; li yueting<br \/>\n<strong>abstract:<\/strong> the present invention relates to a preparation technology of piperic-acid<br \/>\nhealth-care wine which uses pepper or piper longum as raw material, and it is<br \/>\nextracted and mixed with wine to obtain the product which not only possesses wine<br \/>\nflavour, but also possesses the medicinal health-care active of pepper or piper longum.<br \/>\nit can prevent the rise of blood serum cholesterol and formation of choleithiasis.<\/p>\n<p>[35]<br \/>\nboll chim farmaceutico 1998 137(8): 319-320<br \/>\n<strong>\u00ablong chain esters and alkamides from piper longum\u00bb<\/strong><br \/>\nb das, a kashinatham, p madhusudhan<br \/>\n<strong>abstract:<\/strong> from the fruits of piper longum two long chain esters,<br \/>\ntridecyldihydro-p-coumarate and eicosanyl-(E)-p-coumarate and three alkamides,<br \/>\npiperine, piperlongumine and pellitorine have been isolated. the first ester is a<br \/>\nnew compound and the second ester is reported for the first time from this plant.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Piperine from pepper by 3base isolation of piperine (black pepper, EtOH, KOH) isolation of piperine from black pepper (black pepper, EtOH, KOH, soxhlet) isolation of piperine from black pepper (black pepper, IPA, CaCO3) isolation of piperine from black pepper (black pepper, CH2Cl2) isolation of natural piperine (pepper, EtOH, KOH, soxhlet) extraction and isolation (piper nigrum, [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":1644,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[24],"tags":[],"class_list":["post-729","post","type-post","status-publish","format-standard","has-post-thumbnail","category-quimica-avanzada"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.8 - 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