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94-62-2495-91-0 molecular structure
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(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

ChemBase ID: 72970
Molecular Formular: C17H19NO3
Molecular Mass: 285.33766
Monoisotopic Mass: 285.13649347
SMILES and InChIs

SMILES:
C1CN(CCC1)C(=O)/C=C/C=C/c1cc2c(cc1)OCO2
Canonical SMILES:
O=C(N1CCCCC1)/C=C/C=C/c1ccc2c(c1)OCO2
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+
InChIKey:
MXXWOMGUGJBKIW-YPCIICBESA-N

Cite this record

CBID:72970 http://www.chembase.cn/molecule-72970.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
IUPAC Traditional name
bioperine
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Synonyms
1-Piperoylpiperidine
Piperin
Piperine
5-(3,4-methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
piperoylpiperidine
Piperine
(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide
(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one
(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
Bioperine
NSC 21727
Piperin
(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
1-胡椒酰哌啶
胡椒碱
CAS Number
94-62-2495-91-0
94-62-2
EC Number
202-348-0
MDL Number
MFCD00005839
Beilstein Number
90741
Merck Index
147472
PubChem SID
162037890
24901388
24887584
24898568
PubChem CID
638024
CHEMBL
43185
Chemspider ID
553590
FEMA ID
2909
Unique Ingredient Identifier
U71XL721QK
Wikipedia Title
Piperine
Council of Europe Number
492
Flavis Number
14.003

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Lipinski's Rule of Five true  H Acceptors
H Donor LogD (pH = 5.5) 2.7773101 
LogD (pH = 7.4) 2.777311  Log P 2.777311 
Molar Refractivity 82.903 cm3 Polarizability 31.274258 Å3
Polar Surface Area 38.77 Å2 Rotatable Bonds

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
101-103°C expand Show data source
128-131°C expand Show data source
128-132 °C expand Show data source
128-133°C expand Show data source
130°C expand Show data source
131-135 °C(lit.) expand Show data source
Boiling Point
decomposes expand Show data source
Density
1.193 g/cm3 expand Show data source
Organoleptic
pepper; animal expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
TN2321500 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
22-62 expand Show data source
Safety Statements
22-24/25 expand Show data source
36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H301-H361 expand Show data source
H302 expand Show data source
GHS Precautionary statements
P281-P301+P310-P321-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Regulation Compliance
EU Regulation 1334/2008 & 178/2002 expand Show data source
FDA 21 CFR (172.515) expand Show data source
Gene Information
human ... CYP3A4(1576) expand Show data source
Allergens
no known allergens expand Show data source
Mechanism of Action
Activator of the heat and acidity sensing TRPV ion channel TRPV1 on nociceptors (pain sensing nerve cells). expand Show data source
Purity
≥97% expand Show data source
≥98.0% (TLC) expand Show data source
97% expand Show data source
98% expand Show data source
Grade
FG expand Show data source
Halal expand Show data source
Kosher expand Show data source
NI expand Show data source
purum expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Biological Source
Constit. of pepper (Piper nigrum) and many other Piper spp. (Piperaceae) expand Show data source
Application(s)
Analeptic expand Show data source
Bactericidal agent expand Show data source
Empirical Formula (Hill Notation)
C17H19NO3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05217593 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02156273 external link
Purity: 98%
Selleck Chemicals - S2344 external link
Research Area: Neurological Disease
Biological Activity:
Piperine(1-Piperoylpiperidine) is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine (an isomer of piperine). It has also been used in some forms of traditional medicine and as an insecticide. [1]
Toronto Research Chemicals - P483000 external link
The alkaloid which gives pepper its spiciness, and has been used as an organic insecticide.
Sigma Aldrich - W290904 external link
Biochem/physiol Actions
Piperine, a major component of black pepper extracts, shown to have potential for inhibiting fat cell formation.1
Sigma Aldrich - P49007 external link
Packaging
1, 5 g in glass bottle
Application
Reactant for synthesis of:
• Dimeric amide alkaloids1
• Piperoyl-amino acid conjugates used for antileishmanial activity2
• Piperine derived amides with TRPV1 activity3
• Piperine analogues as S. aureus NorA efflux pump inhibitors4
• Bioactive conjugates of curcumin with antimicrobial and antiproliferative properties5
• Piperine derivatives for use as trypanocidal agents6

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Piperine
  • • Trivedi, A., et al.: J. Adv. Pharm. Technol. Res., 1, 190 (2010)
  • • Kakarala, M., et al.: J. Agric. Food Chem., 58, 6594 (2010)
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 362C, (ir)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1379B, (nmr)
  • • Rgheimer, L., Ber., 1882, 15, 1390, (synth, Piperine)
  • • Grewe, R. et al., Chem. Ber., 1970, 103, 3752, (isol, uv, ir, pmr, synth)
  • • Wenkert, E. et al., J.A.C.S., 1971, 93, 6271, (pmr, cmr, Piperine)
  • • Grynpas, M. et al., Acta Cryst. B, 1975, 31, 2663, (cryst struct, Piperine)
  • • DeCleyn, R. et al., Chromatographia, 1975, 8, 342, (isol, uv)
  • • Tsuboi, S. et al., Tet. Lett., 1979, 1043, (synth, Piperine, Isochavicine)
  • • Schulze, A. et al., Annalen, 1981, 1725, (synth)
  • • Kaga, H. et al., Synlett, 1994, 607, (synth, Piperine)
  • • De Araujo-Junior, J.X. et al., Phytochemistry, 1997, 44, 559, (pmr, cmr, Piperine)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PIV600
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PATENTS

PATENTS

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INTERNET

INTERNET

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