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(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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ChemBase ID:
72970
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Molecular Formular:
C17H19NO3
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Molecular Mass:
285.33766
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Monoisotopic Mass:
285.13649347
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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
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Cite this record
CBID:72970 http://www.chembase.cn/molecule-72970.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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IUPAC Traditional name
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bioperine
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(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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Synonyms
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1-Piperoylpiperidine
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Piperin
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Piperine
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5-(3,4-methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
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piperoylpiperidine
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Piperine
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(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide
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(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one
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(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine
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Bioperine
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NSC 21727
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Piperin
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(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
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1-胡椒酰哌啶
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胡椒碱
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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Merck Index
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PubChem SID
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PubChem CID
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CHEMBL
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Chemspider ID
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FEMA ID
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Unique Ingredient Identifier
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Wikipedia Title
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Council of Europe Number
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Flavis Number
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Lipinski's Rule of Five
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true
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H Acceptors
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3
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H Donor
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0
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LogD (pH = 5.5)
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2.7773101
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LogD (pH = 7.4)
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2.777311
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Log P
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2.777311
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Molar Refractivity
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82.903 cm3
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Polarizability
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31.274258 Å3
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Polar Surface Area
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38.77 Å2
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Rotatable Bonds
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3
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DETAILS
DETAILS
MP Biomedicals
Selleck Chemicals
Wikipedia
TRC
Sigma Aldrich
Selleck Chemicals -
S2344
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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] |
Sigma Aldrich -
W290904
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Biochem/physiol Actions Piperine, a major component of black pepper extracts, shown to have potential for inhibiting fat cell formation.1 |
Sigma Aldrich -
P49007
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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
PubMed
Google 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
PubChem Patent
Google Patent