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Ethoxy-carbonyl-methyl ursolate.

Wei Yang¹, Hua-Ling Luo, Cong-Ling Yang

¹College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study synthesized a novel pentacyclic triterpene compound, C(34)H(54)O(5), using ursolic acid. The crystal structure reveals specific chair conformations and intermolecular hydrogen bonding, forming zigzag chains.

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Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Triterpenes, like ursolic acid, are a class of naturally occurring organic compounds with diverse biological activities.
Understanding the structure and synthesis of modified triterpenes is crucial for developing new chemical entities.

Purpose of the Study:

To synthesize a novel pentacyclic triterpene derivative.
To elucidate the molecular structure and conformation of the synthesized compound.
To investigate the intermolecular interactions in the crystal lattice.

Main Methods:

Chemical synthesis involving the reaction of ursolic acid with ethyl chloro-acetate in the presence of N,N-dimethylacetamide (DMA).
X-ray crystallography for determining the precise three-dimensional structure.
Analysis of bond lengths, angles, and conformational preferences.

Main Results:

Successful synthesis of the title compound C(34)H(54)O(5).
All six-membered rings within the pentacyclic triterpene skeleton adopt chair conformations.
Intermolecular O-H⋯O hydrogen bonds link molecules into zigzag chains along the crystallographic c axis.

Conclusions:

The study provides a new synthetic route to a modified ursolic acid derivative.
The conformational analysis confirms the stability of chair conformations in this triterpene system.
The identified hydrogen-bonding network offers insights into crystal packing and intermolecular forces.