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Syntheses and crystal structures of two piperine derivatives.

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 ?-? stacking, as for two of three known piperine polymorphs.

SUBMITTER: Ezawa T

PROVIDER: S-EPMC7199259 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Syntheses and crystal structures of two piperine derivatives.

Ezawa Toshinari T Inoue Yutaka Y Murata Isamu I Suzuki Mitsuaki M Takao Koichi K Sugita Yoshiaki Y Kanamoto Ikuo I

Acta crystallographica. Section E, Crystallographic communications 20200409 Pt 5

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 th ...[more]

PMID: 32431925

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