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Reactions of Carboxylic Acids: Introduction

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

Loss of Carboxy Group as CO₂: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Loss of Carboxy Group as CO₂: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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...

Preparation of Carboxylic Acids: Overview

Preparation of Carboxylic Acids: Overview

There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid. Aldehydes can also be oxidized in the presence of mild oxidizing agents.

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Related Experiment Video

Updated: May 27, 2025

Preparation of Pancreatic Acinar Cells for the Purpose of Calcium Imaging, Cell Injury Measurements, and Adenoviral Infection

Preparation of Pancreatic Acinar Cells for the Purpose of Calcium Imaging, Cell Injury Measurements, and Adenoviral Infection

Published on: July 5, 2013

Fast Release of Carboxylic Acid inside Cells.

Pascal Moser¹, Renaud Zelli¹, Leandro J Dos Santos^1,2

¹Univ. Grenoble Alpes, CNRS, DPM, 38000, Grenoble, France.

|February 17, 2025

Summary

Researchers developed a new prodrug strategy to deliver carboxylic acids into cells. This method uses a cleavable ester to release the acid rapidly inside cells, enhancing drug delivery and efficacy, particularly for antibiotics.

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Preparation of Pancreatic Acinar Cells for the Purpose of Calcium Imaging, Cell Injury Measurements, and Adenoviral Infection

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Measurement and Analysis of Extracellular Acid Production to Determine Glycolytic Rate

Measurement and Analysis of Extracellular Acid Production to Determine Glycolytic Rate

Published on: December 12, 2015

Area of Science:

Chemical Biology
Drug Delivery
Medicinal Chemistry

Background:

Carboxylic acids struggle to cross cell membranes due to ionization at physiological pH.
Ester masking improves cell entry, but rapid intracellular release is crucial for therapeutic control.

Purpose of the Study:

To evaluate a novel 2-hydroxyethyl-dithio-benzyl ester for controlled intracellular carboxylic acid release.
To assess the efficacy of this prodrug strategy for enhancing antibiotic activity.

Main Methods:

Utilized fluorescence-based assays with a pro-fluorescent BODIPY structure.
Investigated the cleavage of the disulfide bond by thioredoxin (Trx) for self-immolation.
Tested levofloxacin ester prodrugs against resistant and intracellular bacteria.

Main Results:

Demonstrated rapid intracellular release of carboxylic acids within minutes in both eukaryotic and prokaryotic cells.
The novel ester functional group enabled efficient release triggered by thioredoxin.
Levofloxacin ester prodrug showed significantly enhanced antimicrobial activity compared to its methyl ester analogue.

Conclusions:

The 2-hydroxyethyl-dithio-benzyl ester is an effective tool for rapid intracellular carboxylic acid release.
This prodrug strategy offers a promising approach for developing improved therapeutics, especially against resistant bacteria.