Piperine

Piperine
Piperine
Scoville scale	150,000 SHU

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-(Benzo[d] [1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one; Piperoylpiperidine; Bioperine
Identifiers
CAS Number	94-62-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28821 ;
ChEMBL	ChEMBL43185 ;
ChemSpider	553590 ;
ECHA InfoCard	100.002.135
IUPHAR/BPS	2489;
PubChem CID	638024;
UNII	U71XL721QK ;
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+ Key: MXXWOMGUGJBKIW-YPCIICBESA-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	285.343 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 [77 °F], 100 kPa). verify (what is ?) Infobox references

Piperine, possibly along with its isomer chavicine,^[2] is the compound^[3] responsible for the pungency of black pepper and long pepper via activation of TRPV1.^[4] It has been used in some forms of traditional medicine.^[5]

^ Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN 9789332520264.
^ Cite error: The named reference De_Cleyn&Verzele1972 was invoked but never defined (see the help page).
^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. p. 7442. ISBN 091191028X.
^ Dong, Y; Yin, Y; Vu, S; Yang, F; Yarov-Yarovoy, V; Tian, Y; Zheng, J (20 August 2019). "A distinct structural mechanism underlies TRPV1 activation by piperine". Biochemical and Biophysical Research Communications. 516 (2): 365–372. Bibcode:2019BBRC..516..365D. doi:10.1016/j.bbrc.2019.06.039. PMC 6626684. PMID 31213294.
^ Srinivasan, K. (2007). "Black pepper and its pungent principle-piperine: A review of diverse physiological effects". Critical Reviews in Food Science and Nutrition. 47 (8): 735–748. doi:10.1080/10408390601062054. PMID 17987447. S2CID 42908718.

[1] Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN 9789332520264.

[De_Cleyn&Verzele1972-2] Cite error: The named reference De_Cleyn&Verzele1972 was invoked but never defined (see the help page).

[3] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. p. 7442. ISBN 091191028X.

[4] Dong, Y; Yin, Y; Vu, S; Yang, F; Yarov-Yarovoy, V; Tian, Y; Zheng, J (20 August 2019). "A distinct structural mechanism underlies TRPV1 activation by piperine". Biochemical and Biophysical Research Communications. 516 (2): 365–372. Bibcode:2019BBRC..516..365D. doi:10.1016/j.bbrc.2019.06.039. PMC 6626684. PMID 31213294.

[5] Srinivasan, K. (2007). "Black pepper and its pungent principle-piperine: A review of diverse physiological effects". Critical Reviews in Food Science and Nutrition. 47 (8): 735–748. doi:10.1080/10408390601062054. PMID 17987447. S2CID 42908718.

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