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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

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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Related Categories

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

hcodes

H302,H411

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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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)
Shiv K Dubey et al.
European journal of medicinal chemistry, 43(9), 1837-1846 (2008-01-19)
The monoesters of curcumin, a symmetric diphenol with valine and glycine have been prepared by a novel solid phase synthesis and its diesters with valine, glutamic acid and demethylenated piperic acid have been prepared by solution phase method. The assessment
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
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
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