piperine piperine piperine, along with its isomer chavicine, is the compound responsible for the pungency of black pepper and long pepper. it has been used in some forms of traditional medicine. not to be confused with piperidine. piperine names preferred iupac name (2e,4e)-5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one other names (2e,4e)-5-(benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-onepiperoylpiperidinebioperine identifiers cas number 94-62-2 y 3d model (jsmol) interactive image chebi chebi:28821 n chembl chembl43185 n chemspider 553590 n echa infocard 100.002.135 iuphar/bps 2489 pubchem cid 638024 unii u71xl721qk n comptox dashboard (epa) dtxsid3021805 inchi inchi=1s/c17h19no3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12h,1,4-5,10-11,13h2/b6-2+,7-3+ nkey: mxxwomgugjbkiw-ypciicbesa-n ninchi=1/c17h19no3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12h,1,4-5,10-11,13h2/b6-2+,7-3+key: mxxwomgugjbkiw-ypciicbeby smiles o=c(n1ccccc1)\c=c\c=c\c2ccc3ococ3c2 properties chemical formula c17h19no3 molar mass 285.343 g·mol−1 density 1.193 g/cm3 melting point 130 °c (266 °f; 403 k) boiling point decomposes solubility in water 40 mg/l solubility in ethanol soluble solubility in chloroform 1 g/1.7 ml hazards safety data sheet (sds) msds for piperine except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references piperinescoville scale150,000 shu preparation due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane. the amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers. piperine can also be prepared by treating a concentrated alcoholic extract of black pepper with an alcoholic solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine). the solution is decanted from the insoluble residue and left to stand overnight. during this period, the alkaloid slowly crystallizes from the solution. piperine has been synthesized by the action of piperonoyl chloride on piperidine. reactions piperine forms salts only with strong acids. the platinichloride b4·h2ptcl6 forms orange-red needles ("b" denotes one mole of the alkaloid base in this and the following formula). iodine in potassium iodide added to an alcoholic solution of the base in the presence of a little hydrochloric acid gives a characteristic periodide, b2·hi·i2, crystallizing in steel-blue needles with melting point 145 °c. piperine can be hydrolyzed by an alkali into piperidine and piperic acid. history piperine was discovered in 1819 by hans christian ørsted, who isolated it from the fruits of piper nigrum, the source plant of both black and white pepper. piperine was also found in piper longum and piper officinarum (miq.) c. dc. (=piper retrofractum vahl), two species called "long pepper". biochemistry and medicinal aspects a component of pungency by piperine results from activation of the heat- and acidity-sensing transient receptor potential channel ion channels, trpv1 and trpa1, on nociceptors, the pain-sensing nerve cells. piperine is under preliminary research for its potential to affect bioavailability of other compounds in food and dietary supplements, such as a possible effect on the bioavailability of curcumin.