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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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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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γ-Cyclodextrin.

Phennapha Saokham1, Thorsteinn Loftsson1

  • 1Faculty of Pharmaceutical Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavik, Iceland.

International Journal of Pharmaceutics
|December 20, 2016
PubMed
Summary
This summary is machine-generated.

Gamma-cyclodextrin (γCD), a starch derivative, offers superior solubility and a favorable safety profile compared to other cyclodextrins. Its negligible bioavailability and excretion make it a safe excipient for pharmaceutical and food applications.

Keywords:
ADMEAggregationComplexing agentInclusion complexSolubilizationγ-Cyclodextrin

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Area of Science:

  • Biochemistry and Pharmaceutical Sciences
  • Food Science and Technology

Background:

  • Gamma-cyclodextrin (γCD) is a cyclic oligosaccharide derived from starch.
  • It functions as a solubilizing agent and stabilizer in pharmaceutical and food products.
  • γCD exhibits a large hydrophobic cavity, high water solubility, and a favorable toxicological profile compared to αCD and βCD.

Purpose of the Study:

  • To review the production, physiochemical properties, pharmacokinetics, and toxicity of γCD and its derivatives.
  • To discuss the applications of γCD in various industries.
  • To explore the aggregation behavior of γCD in aqueous media.

Main Methods:

  • Literature review focusing on scientific publications related to γCD.
  • Analysis of physiochemical properties, pharmacokinetic data, and toxicological studies.
  • Discussion of reported applications and aggregation phenomena.

Main Results:

  • γCD is poorly bioavailable due to rapid gastrointestinal digestion and metabolism by α-amylase.
  • It is readily excreted unchanged in urine after parenteral administration.
  • γCD forms water-soluble inclusion complexes with poorly soluble compounds.

Conclusions:

  • γCD possesses advantageous properties, including high solubility and a favorable safety profile, making it suitable for pharmaceutical and food applications.
  • Its negligible bioavailability and rapid excretion contribute to its safety.
  • Further research into its derivatives and aggregation behavior is warranted.