Piperine

Piperine

Names
IUPAC name 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine
Other names 5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine Piperoylpiperidine Bioperine
Identifiers
CAS Number	94-62-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28821 N
ChEMBL	ChEMBL43185 N
ChemSpider	553590 N
ECHA InfoCard	100.002.135
IUPHAR/BPS	2489
PubChem	638024
UNII	U71XL721QK N
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+ N Key: MXXWOMGUGJBKIW-YPCIICBESA-N N InChI=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	285.34 g·mol−1
Density	1.193 g/cm3
Melting point	130 °C (266 °F; 403 K)
Boiling point	decomposes
Solubility in water	40mg/L
Solubility in alcohol	1g/15ml
Solubility in ether	1g/36ml
Solubility in chloroform	1g/1.7ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Piperine
Heat	(SR: 100,000)

Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has also been used in some forms of traditional medicine and as an insecticide.

Piperine is extracted from black pepper using dichloromethane. Aqueous hydrotropes can be used in the extraction to result in high yield and selectivity. The amount of piperine varies from 1-2% in long pepper, to 5-10% in commercial white and black peppers. Further, it may be prepared by treating the solvent-free residue from an alcoholic extract of black pepper, with a solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine) and solution of the washed, insoluble residue in warm alcohol, from which the alkaloid crystallises on cooling.

Piperine yields 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 formulae.) 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, crystallising in steel-blue needles, mp. 145 °C.

Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of Piper nigrum, the source plant of both the black and white pepper grains. Flückiger and Hanbury found piperine in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper".West African pepper also contains piperine.