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Related Concept Videos

Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Overview of Fatty Acid Metabolism01:28

Overview of Fatty Acid Metabolism

Lipids also are sources of energy that power cellular processes. Like carbohydrates, lipids are composed of carbon, hydrogen, and oxygen, but these atoms are arranged differently. Most lipids are nonpolar and hydrophobic. Major types include fats and oils, waxes, phospholipids, and steroids.
Fatty acids are catabolized in a process called beta-oxidation, which takes place in the matrix of the mitochondria and converts their fatty acid chains into two-carbon units of acetyl groups. The acetyl...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Synthesis of Phosphatidylcholine in the ER Membrane01:27

Synthesis of Phosphatidylcholine in the ER Membrane

The ER synthesizes lipids for building cell membranes and performing cellular functions such as energy storage and signaling. The lipid synthesis machinery embedded in the ER membrane primarily collects all reactants from the cytosol. Following synthesis, the secretory pathway and the ER contact sites distribute these lipids to other cellular organelles. Additionally, the energy-rich triacylglycerides are transported from the ER via lipid droplets.
The major components of all eukaryotic cell...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...

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Related Experiment Video

Updated: Jun 1, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

3-Methyl-5α-cholest-2-ene.

Kamal Aziz Ketuly1, A Hamid A Hadi, Seik Weng Ng

  • 1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online
|May 19, 2011
PubMed
Summary

This study analyzes a cholestane derivative, revealing its cyclo-hexene ring adopts a half-chair conformation. This structure closely resembles the parent 5α-cholest-2-ene molecule.

Area of Science:

  • Steroid chemistry
  • Organic chemistry
  • Structural analysis

Background:

  • Cholestane derivatives are complex molecules with diverse biological activities.
  • Understanding the conformational preferences of these steroids is crucial for structure-activity relationship studies.
  • The specific cholestane derivative (C28H48) investigated here presents a unique structural motif.

Purpose of the Study:

  • To determine the three-dimensional structure and conformational analysis of a specific cholestane derivative.
  • To compare the conformation of the cyclo-hexene ring in the derivative with its parent compound, 5α-cholest-2-ene.

Main Methods:

  • X-ray crystallography or computational modeling was used to elucidate the structure.
  • Conformational analysis was performed on the cholestane derivative.

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  • Superimposition analysis was conducted by comparing the derivative's fragment with 5α-cholest-2-ene.

    • Main Results:

    • The cyclo-hexene ring within the cholestane derivative adopts a half-chair conformation.
    • The fragment of the title compound corresponding to the cyclo-hexene ring is nearly identical to 5α-cholest-2-ene.
    • Root-mean-square deviation (r.m.s.d.) of 0.033 Å indicates high structural similarity.

    Conclusions:

    • The cholestane derivative maintains a conformationally similar cyclo-hexene ring to its parent compound.
    • This finding contributes to the understanding of steroid conformational dynamics.
    • The structural data can inform future research on related steroid compounds.