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P49007

Sigma-Aldrich

Piperine

≥97%

Synonym(s):

(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide, 1-Piperoylpiperidine

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About This Item

Empirical Formula (Hill Notation):
C17H19NO3
CAS Number:
94-62-2
Molecular Weight:
285.34
Beilstein/REAXYS Number:
90741
EC Number:
202-348-0
MDL number:
MFCD00005839
UNSPSC Code:
12352100
PubChem Substance ID:
24898568
NACRES:
NA.22

Quality Level

100

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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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
GHS07,GHS09

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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V. R. S. Rao, et al.,
Tetrahedron, 67, 1885-1892 (2011)
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
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
Welisson da Silva Ferreira et al.
Bioorganic & medicinal chemistry, 16(6), 2984-2991 (2008-01-30)
We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that
Clara Grosso et al.
Phytochemical analysis : PCA, 24(2), 141-147 (2012-09-19)
Depression is a mental disease causing large personal and socio-economic problems, and new improved drugs are therefore needed. Selective monoamine oxidase A (MAO-A) inhibitors are potential anti-depressants, but discovering new MAO-A inhibitors from natural sources by bioassay-guided approaches are a
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