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Related Experiment Videos

Transesterification: an analytical and formulation problem.

W J Irwin1, Q N Masuda, A Li Wan Po

  • 1Pharmaceutics Research Group, Division of Pharmaceutics and Pharmaceutical Chemistry, Department of Pharmacy, University of Aston in Birmingham, Gosta Green, Birmingham B4 7ET, UK.

Journal of Pharmaceutical and Biomedical Analysis
|January 1, 1985
PubMed
Summary
This summary is machine-generated.

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Esters like salicylates can reverse transesterification in alcohol solutions. These reactions also occur in topical products, potentially affecting pharmaceutical stability and delivery.

Area of Science:

  • Pharmaceutical Chemistry
  • Organic Chemistry

Background:

  • Esters such as salicylates, nicotinates, and parabens are common in pharmaceutical formulations.
  • Transesterification is a known chemical reaction involving esters.

Purpose of the Study:

  • To investigate the occurrence and implications of base-catalyzed transesterification and oligomerization of esters in various solutions and topical formulations.
  • To highlight the potential impact of these reactions on pharmaceutical stability and delivery.

Main Methods:

  • Studied transesterification of salicylates, nicotinates, and parabens in hydroalcoholic solutions.
  • Investigated phenyl salicylate oligomerization in non-alcoholic solutions.
  • Examined reactions in topical product vehicles containing alcohol, glycol, or glycol polymers.

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Main Results:

  • Reversible, base-catalyzed transesterification was observed for various esters in hydroalcoholic solutions.
  • Phenyl salicylate underwent concentration-dependent oligomerization in non-alcoholic media, forming salsalate and other products.
  • Transesterification reactions were confirmed in topical formulations with alcohol-based vehicles.

Conclusions:

  • Transesterification and oligomerization reactions involving common esters can occur in both solutions and topical formulations.
  • These reactions, if unrecognized, pose risks to the stability, integrity, and delivery profiles of pharmaceutical products.
  • Awareness and consideration of these chemical transformations are crucial for accurate pharmaceutical development and assessment.