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P49007

Sigma-Aldrich

Piperine

≥97%

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Synonym(s):
(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide, 1-Piperoylpiperidine
Empirical Formula (Hill Notation):
C17H19NO3
CAS Number:
Molecular Weight:
285.34
Beilstein/REAXYS Number:
90741
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97%

form

crystalline
powder, crystals or chunks
solid

mp

131-135 °C (lit.)

SMILES string

O=C(\C=C\C=C\c1ccc2OCOc2c1)N3CCCCC3

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+

InChI key

MXXWOMGUGJBKIW-YPCIICBESA-N

Gene Information

human ... CYP3A4(1576)

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This Item
W290904PHR22111543200
Piperine ≥97%

P49007

Piperine

Piperine ≥95%, FG

W290904

Piperine

Piperine Pharmaceutical Secondary Standard; Certified Reference Material

PHR2211

Piperine

Piperine United States Pharmacopeia (USP) Reference Standard

1543200

Piperine

Quality Level

100

Quality Level

400

Quality Level

300

Quality Level

-

form

crystalline, solid, powder, crystals or chunks

form

powder, crystals or granules

form

solid

form

-

mp

131-135 °C (lit.)

mp

131-135 °C (lit.)

mp

131-135 °C (lit.)

mp

131-135 °C (lit.)

Gene Information

human ... CYP3A4(1576)

Gene Information

human ... CYP3A4(1576)

Gene Information

-

Gene Information

-

Application

Reactant for synthesis of:
  • Dimeric amide alkaloids
  • Piperoyl-amino acid conjugates used for antileishmanial activity
  • Piperine derived amides with TRPV1 activity
  • Piperine analogues as S. aureus NorA efflux pump inhibitors
  • Bioactive conjugates of curcumin with antimicrobial and antiproliferative properties
  • Piperine derivatives for use as trypanocidal agents

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Jiu-Wang Yu et al.
Molecular diversity, 25(1), 233-248 (2020-03-05)
Piperine is the main active component of Piper longum L., which is also the main component of anti-sciatica Mongolian medicine Naru Sanwei pill. It has many pharmacological activities such as anti-inflammatory and immune regulation. This paper aims to preliminarily explore
V. R. S. Rao, et al.,
Tetrahedron, 67, 1885-1892 (2011)
Janine Zaugg et al.
Journal of natural products, 73(2), 185-191 (2010-01-21)
A plant extract library was screened for GABA(A) receptor activity making use of a two-microelectrode voltage clamp assay on Xenopus laevis oocytes. An ethyl acetate extract of black pepper fruits [Piper nigrum L. (Piperaceae) 100 microg/mL] potentiated GABA-induced chloride currents
Paul B Yaffe et al.
Experimental and molecular pathology, 94(1), 109-114 (2012-10-16)
Piperine, an alkaloid phytochemical found in the fruit of black and long pepper plants, is reported to inhibit the growth of cancer cells; however, the mechanism of action in human cancer cells is not clear. In this study we investigated
Sophia Khom et al.
Biochemical pharmacology, 85(12), 1827-1836 (2013-04-30)
The action of piperine (the pungent component of pepper) and its derivative SCT-66 ((2E,4E)-5-(1,3-benzodioxol-5-yl))-N,N-diisobutyl-2,4-pentadienamide) on different gamma-aminobutyric acid (GABA) type A (GABA(A)) receptors, transient-receptor-potential-vanilloid-1 (TRPV1) receptors and behavioural effects were investigated. GABA(A) receptor subtypes and TRPV1 receptors were expressed in

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