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Related Concept Videos

Cholesterol: Significance and Regulation01:29

Cholesterol: Significance and Regulation

Although not a source of energy, cholesterol plays a significant role as a foundational structure for bile salts, steroid hormones, and vitamin D, as well as being a crucial component of plasma membranes. Approximately 15% of blood cholesterol is derived from our diet, with the remainder synthesized from acetyl CoA by the liver and intestines. Cholesterol is eliminated from the body through its conversion into bile salts, which are eventually discarded in the feces.
Considering cholesterol and...
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...
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...
Chirality in Nature02:30

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...
Esters to β-Ketoesters: Claisen Condensation Overview01:24

Esters to β-Ketoesters: Claisen Condensation Overview

Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
Aldol Condensation vs Claisen Condensation01:33

Aldol Condensation vs Claisen Condensation

Aldol condensation is an acid or base-catalyzed condensation between aldehydes or ketones to give an α,ꞵ-unsaturated carbonyl compound. A base-promoted condensation between ester molecules to produce a ꞵ-ketoester is known as the Claisen condensation. In the presence of a base, both reactions involve deprotonation of the acidic α hydrogen to produce the corresponding enolates. The nucleophilic enolates attack their respective nonenolized carbonyl compound forming a tetrahedral intermediate.

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Related Experiment Video

Updated: Jun 4, 2026

Enrichment of Mammalian Tissues and Xenopus Oocytes with Cholesterol
10:12

Enrichment of Mammalian Tissues and Xenopus Oocytes with Cholesterol

Published on: March 25, 2020

The origin of cholesterol's condensing effect.

Trevor A Daly1, Minghui Wang, Steven L Regen

  • 1Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, United States.

Langmuir : the ACS Journal of Surfaces and Colloids
|February 16, 2011
PubMed
Summary

Cholesterol and dihydrocholesterol strongly condense fluid bilayers, unlike coprostanol. This supports a template mechanism for lipid bilayer condensation, refuting an umbrella model.

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Cholesterol Efflux Assay
07:54

Cholesterol Efflux Assay

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Differential Effects of Lipid-lowering Drugs in Modulating Morphology of Cholesterol Particles
09:15

Differential Effects of Lipid-lowering Drugs in Modulating Morphology of Cholesterol Particles

Published on: November 10, 2017

Related Experiment Videos

Last Updated: Jun 4, 2026

Enrichment of Mammalian Tissues and Xenopus Oocytes with Cholesterol
10:12

Enrichment of Mammalian Tissues and Xenopus Oocytes with Cholesterol

Published on: March 25, 2020

Cholesterol Efflux Assay
07:54

Cholesterol Efflux Assay

Published on: March 6, 2012

Differential Effects of Lipid-lowering Drugs in Modulating Morphology of Cholesterol Particles
09:15

Differential Effects of Lipid-lowering Drugs in Modulating Morphology of Cholesterol Particles

Published on: November 10, 2017

Area of Science:

  • Biochemistry
  • Membrane Biophysics
  • Lipid Bilayer Dynamics

Background:

  • Cholesterol is a key component of animal cell membranes, influencing their fluidity and organization.
  • Sterols like cholesterol modulate the physical properties of lipid bilayers.
  • Understanding sterol-membrane interactions is crucial for cell biology.

Purpose of the Study:

  • To compare the condensing effects of cholesterol, dihydrocholesterol, and coprostanol on 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid bilayers.
  • To investigate the mechanism of sterol-induced lipid bilayer condensation.

Main Methods:

  • Nearest-neighbor recognition measurements were employed to quantify the condensing effects.
  • Fluid bilayers composed of DPPC were utilized as the model system.

Main Results:

  • Dihydrocholesterol demonstrated a condensing power comparable to that of cholesterol.
  • Coprostanol exhibited a significantly weaker condensing effect compared to cholesterol and dihydrocholesterol.
  • The differential condensing activities suggest distinct molecular interactions.

Conclusions:

  • The findings strongly support a template mechanism for sterol-induced condensation in lipid bilayers.
  • The results argue against an umbrella mechanism for sterol condensation.
  • The structural differences between these sterols dictate their efficacy in modulating membrane properties.