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Related Concept Videos

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

3.0K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
3.7K
Esters to β-Ketoesters: Claisen Condensation Overview01:24

Esters to β-Ketoesters: Claisen Condensation Overview

4.0K
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.
4.0K
Bioavailability Enhancement: Drug Stability Enhancement and GI Retention01:05

Bioavailability Enhancement: Drug Stability Enhancement and GI Retention

139
Body:Improving a drug's stability in the gastrointestinal (GI) tract is paramount for enhancing its bioavailability and therapeutic effectiveness. Various strategies are employed to protect the drug from the harsh gastric milieu and to ensure its release and absorption at the desired site within the GI tract.Polymer coatings are one such method used to shield drugs from the stomach's acidic environment. By preventing premature drug release, these coatings improve the bioavailability of unstable...
139
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.6K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.6K
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

4.5K
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...
4.5K

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Related Experiment Video

Updated: Dec 22, 2025

Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study
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Transport Properties of Ibuprofen Encapsulated in Cyclodextrin Nanosponge Hydrogels: A Proton HR-MAS NMR Spectroscopy Study

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Sulfobutylether-β-cyclodextrin.

Valentino J Stella1, Roger A Rajewski1

  • 1Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, USA.

International Journal of Pharmaceutics
|May 8, 2020
PubMed
Summary
This summary is machine-generated.

Sulfobutylether-β-cyclodextrin (Captisol®) is a safe parenteral solubilizer and stabilizer. This review details its discovery and development, highlighting its use in numerous FDA-approved injectables.

Keywords:
CaptisolCyclodextrinFormulationSafetySolubilityStabilitySynthesis

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Area of Science:

  • Pharmaceutical Sciences
  • Drug Delivery Systems
  • Chemical Engineering

Background:

  • Review of the early history, motivation, and research behind sulfobutylether-β-cyclodextrin.
  • Exploration of the discovery and development process of this novel excipient.

Observation:

  • Sulfobutylether-β-cyclodextrin, specifically Captisol® (average degree of 6.5 sulfobutyl-groups), acts as a parenterally safe solubilizer and stabilizer.
  • Detailed chemical structure involving variable substitution on β-cyclodextrin's glucopyranose units.

Findings:

  • Captisol® is currently incorporated into 13 FDA-approved injectable drugs.
  • Numerous clinical candidates also utilize this advanced drug delivery technology.

Implications:

  • Demonstrates a successful academic-to-industry transition for a novel pharmaceutical product.
  • Highlights the significant impact of specialized cyclodextrins in modern medicine and drug formulation.