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Diosgenin-3,6-dione: second polymorph in space group P212121.

Gabriel Guerrero-Luna1, Jaquelin Reyes Melchor2, Sylvain Bernès3

  • 1Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico.

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Summary

This study details a second polymorph of a steroid derivative, [(25R)-spirost-4-en-3,6-dione], identified through crystal structure analysis. The new form shares the same space group but exhibits subtle conformational differences in its steroid nucleus.

Keywords:
crystal structurediosgeninpolymorphismsteroids

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Area of Science:

  • Crystallography and Materials Science
  • Organic Chemistry and Steroid Chemistry

Background:

  • The steroid [(25R)-spirost-4-en-3,6-dione] is synthesized via diosgenin oxidation.
  • Previous crystal structure reports contained inaccuracies regarding absolute configuration and hydrogen atom positions.

Purpose of the Study:

  • To characterize a second polymorph of [(25R)-spirost-4-en-3,6-dione].
  • To refine the understanding of its crystal structure and polymorphism.

Main Methods:

  • Oxidation of diosgenin using Jones reagent (CrO3/H2SO4).
  • X-ray diffraction data collection and analysis.
  • Simulated powder pattern analysis for polymorph identification.

Main Results:

  • A second polymorph of [(25R)-spirost-4-en-3,6-dione] was identified in the same space group (P212121) as the previously reported form.
  • Both polymorphs exhibit similar ortho-rhom-bic unit cells and molecular arrangements.
  • A slight modification in the conformation of the A/B rings of the steroid nucleus distinguishes the two polymorphs.

Conclusions:

  • The study successfully identified and characterized a new polymorph of [(25R)-spirost-4-en-3,6-dione].
  • Polymorphism in this steroid is attributed to subtle conformational changes within the steroid nucleus.
  • This work corrects and expands upon previous crystallographic data for this compound.