Related Experiment Video
Updated: Aug 3, 2025
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
36.1K
Structural Insights and Intermolecular Energy for Some Medium and Long-Chain Testosterone Esters
Alexandru Turza1, Petru Pascuta2, Liviu Mare2
1National Institute For R&D of Isotopic and Molecular Technologies, 67-103 Donat, 400293 Cluj-Napoca, Romania.
Molecules (Basel, Switzerland)
|April 13, 2023
Summary
This study determined the crystal structures of four testosterone esters, revealing insights into their molecular arrangements and intermolecular interactions. These findings enhance our understanding of testosterone ester properties for pharmaceutical applications.
Area of Science:
- Crystallography
- Materials Science
- Pharmaceutical Chemistry
Background:
- Testosterone (17β-Hydroxyandrost-4-en-3-one) is the principal male anabolic-androgenic steroid.
- Esterification of testosterone is a common strategy to modify its pharmacokinetic properties for therapeutic use.
Purpose of the Study:
- To determine the crystal structures of medium and long-chain testosterone esters.
- To characterize their solid-state properties and supramolecular arrangements.
- To investigate their pharmaceutical relevance, including solubility.
Main Methods:
- X-ray single crystal diffraction for precise structure determination.
- Powder X-ray diffraction, FT-IR spectroscopy, and thermal analysis (DTA, TG) for material characterization.
- Computational methods, including Hirshfeld surface analysis, for analyzing intermolecular interactions and crystal energies.
Main Results:
- Detailed crystal structures and packing arrangements were elucidated for testosterone enanthate, cypionate, decanoate, and undecanoate.
- Solid-state characterization confirmed the identity and purity of the crystalline forms.
- Computational analysis provided insights into the nature and strength of intermolecular forces governing crystal structures.
- Solubility investigations were performed to assess pharmaceutical implications.
Conclusions:
- The study provides a comprehensive structural and physicochemical characterization of key testosterone esters.
- Understanding crystal packing and intermolecular interactions is crucial for predicting and optimizing drug properties.
- The findings contribute to the rational design and development of testosterone-based pharmaceuticals.
Related Concept Videos
02:18Conformations of Ethane and Propane
14.1K
In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
14.1K
02:30Stability of Substituted Cyclohexanes
12.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
12.7K
01:28Stability of Conjugated Dienes
3.5K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.5K
02:14Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes
6.4K
The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified...
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified...
6.4K
01:59Relative Stabilities of Alkenes
14.1K
The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene. The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
14.1K
02:49Bond Energies and Bond Lengths
25.4K
Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
25.4K