Related Experiment Video
Updated: Oct 11, 2026

Synthesis of Soft Polysiloxane-urea Elastomers for Intraocular Lens Application
Published on: March 8, 2019
Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters)
1Department of Chemistry, Rutgers University, Piscataway, NJ 08854-8087, USA.
Abstract:
A biodegradable poly(anhydride-ester) was synthesized by melt condensation polymerization of the acetylated monomer to yield a novel polymeric prodrug. The polymer we have synthesized is composed of alkyl chains linked by ester bonds to aromatic moieties, specifically salicylic acid--the active component of aspirin. With the medicinal properties attributed to salicylic acid and the ease of metabolism, the incorporation of this compound into a polymer backbone yields a polymeric prodrug that may have potential in a variety of applications (i.e., inflammatory bowel disease). For these reasons, we have designed a synthetic scheme that yields the desired poly(anhydride-ester). The in vitro hydrolytic degradation of these polymers has been performed and results indicate that the polymer degradation rate is pH-dependent.
Related Concept Videos
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Esters to Carboxylic Acids: Saponification
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Alkylation of β-Diester Enolates: Malonic Ester Synthesis

