Syntheses and crystal structures of two piperine derivatives

Toshinari Ezawa; Yutaka Inoue; Isamu Murata; Mitsuaki Suzuki; Koichi Takao; Yoshiaki Sugita; Ikuo Kanamoto

doi:10.1107/S2056989020004648

Syntheses and crystal structures of two piperine derivatives

Acta Crystallogr E Crystallogr Commun. 2020 Apr 9;76(Pt 5):646-650. doi: 10.1107/S2056989020004648. eCollection 2020 May 1.

Authors

Toshinari Ezawa¹, Yutaka Inoue¹, Isamu Murata¹, Mitsuaki Suzuki², Koichi Takao¹, Yoshiaki Sugita¹, Ikuo Kanamoto¹

Affiliations

¹ Faculty of Pharmacy and Pharmaceutical Science, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 3500295, Japan.
² Faculty of Science, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 3500295, Japan.

Abstract

The title compounds, 5-(2H-1,3-benzodioxol-5-yl)-N-cyclo-hexyl-penta-2,4-dienamide, C₁₈H₂₁NO₃ (I), and 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C₁₆H₁₇NO₃ (II), are derivatives of piperine, which is known as a pungent component of pepper. Their geometrical parameters are similar to those of the three polymorphs of piperine, which indicate conjugation of electrons over the length of the mol-ecules. The extended structure of (I) features N-H⋯O amide hydrogen bonds, which generate C(4) [010] chains. The crystal of (II) features aromatic π-π stacking, as for two of three known piperine polymorphs.

Keywords: crystal structure; hydrogen bond; organic crystal; piperine.

Grants and funding

This work was funded by Josai University grant .