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Acylation of ascorbic acid in water.

R B Paulssen, D Chatterji, T Higuchi

    Journal of Pharmaceutical Sciences
    |August 1, 1975
    PubMed
    Summary
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    Ascorbic acid acylation with acetic anhydride yields acetic acid and 3-O-acetylascorbic acid. Reaction pathways diverge based on pH, impacting ascorbic acid ester structural assignments.

    Area of Science:

    • Organic Chemistry
    • Biochemistry

    Background:

    • Ascorbic acid (Vitamin C) is a vital nutrient with various biological roles.
    • Understanding the chemical modifications of ascorbic acid is crucial for its applications and stability.

    Purpose of the Study:

    • To investigate the reaction products and kinetics of ascorbic acid acylation using acetic anhydride.
    • To elucidate the pH-dependent reaction pathways of intermediate products.

    Main Methods:

    • Studied the acylation of ascorbic acid with acetic anhydride in aqueous solution at 25°C.
    • Analyzed reaction products and determined predominant pathways at different pH values (below 4 and between 4-7).

    Main Results:

    • Initial reaction products identified as acetic acid and 3-O-acetylascorbic acid.

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  • 3-O-acetylascorbic acid undergoes parallel hydrolysis and intramolecular acyl migration.
  • Hydrolysis dominates below pH 4; acyl migration predominates between pH 4-7.

    • Conclusions:

    • The study clarifies the complex reaction mechanisms in ascorbic acid acylation.
    • Findings challenge existing structural assignments for certain ascorbic acid esters.
    • Provides a basis for re-evaluating the stability and synthesis of ascorbic acid derivatives.