Piperlonguminine

Piperlonguminine
Names
Preferred IUPAC name
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+
    Key: WHAAPCGHVWVUEX-GGWOSOGESA-N
  • InChI=1/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+
    Key: WHAAPCGHVWVUEX-GGWOSOGEBI
  • CC(C)CNC(=O)/C=C/C=C/C1=CC2=C(C=C1)OCO2
Properties
C16H19NO3
Molar mass 273.332 g·mol−1
Melting point 167-169 °C (332.6-336.2 °F; 440-442K)
Solubility DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Piperlonguminine is an alkaloid amide isolated from Piper longum, commonly known as the long pepper.[1][2]

References

  1. ^ Kim, KS; Kim, JA; Eom, SY; Lee, SH; Min, KR; Kim, Y (February 2006). "Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression". Pigment Cell Research. 19 (1): 90–8. doi:10.1111/j.1600-0749.2005.00281.x. PMID 16420250.
  2. ^ Lee, W; Yoo, H; Kim, J. A; Lee, S; Jee, J. G; Lee, M. Y; Lee, Y. M; Bae, J. S (2013). "Barrier protective effects of piperlonguminine in LPS-induced inflammation in vitro and in vivo". Food and Chemical Toxicology. 58: 149–57. doi:10.1016/j.fct.2013.04.027. PMID 23619565.


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