Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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

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

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

Esters to Carboxylic Acids: Saponification

Esters to Carboxylic Acids: Saponification

Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...

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.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Delirium Leads to Poor In-Hospital and 90-Day Outcomes Among Patients With Acute Ischemic Stroke With and Without Intravenous Thrombolysis or Intraarterial Therapy.

Stroke (Hoboken, N.J.)·2026

Same author

Stroke Severity Mediates the Association Between Socioeconomic Disadvantage and Poor Outcomes Among Patients With Acute Ischemic Stroke.

Stroke (Hoboken, N.J.)·2026

Same author

Social Disparities, Delirium Occurrence, and Related Outcomes Among Hospitalized Older Adults.

Journal of the American Geriatrics Society·2025

Same author

Development of a Natural Language Processing Model for Extracting Kidney Biopsy Pathology Diagnoses.

Kidney medicine·2025

Same author

Postacute Discharge Destination and Major Adverse Cardiovascular Events Among Patients With Intracerebral Hemorrhage.

Stroke·2025

Same author

Ethanol Inhalation as a Method to Denature the Spike Protein of SARS-CoV-2.

Advances in experimental medicine and biology·2024

Search research articles

Related Experiment Video

Updated: Jul 3, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Naturally occurring esterification reactions with bryostatin.

Giso Abadi¹, Thomas J Manning, Kristen McLeod

¹Chemistry and Pharmacy, Sunderland University, Sunderland, United Kingdom.

Natural Product Research

|July 16, 2008

Summary

Bryostatins can change structure under natural conditions and through hydrolysis by water. These reactions impact medicinal uses and extraction methods for these complex molecules.

More Related Videos

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Related Experiment Videos

Last Updated: Jul 3, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Area of Science:

Natural Product Chemistry
Organic Chemistry
Analytical Chemistry

Background:

Bryostatins are complex natural products with a shared bryophan ring structure.
Variations in bryostatin structures arise from differing R(1) and R(2) groups attached via ester bonds.

Purpose of the Study:

To investigate the stability of bryostatin structures under various environmental conditions.
To understand the impact of UV light, acidic, and basic conditions on bryostatin.

Main Methods:

Mass spectrometry (MS) was employed to analyze structural changes in bryostatin.
Experiments were conducted in the presence of octanoic acid and water to simulate natural conditions.

Main Results:

Bryostatin undergoes structural rearrangements when exposed to carboxylates, which are common in nature.
Hydrolysis by water was observed, indicating a significant degradation pathway for bryostatin.

Conclusions:

Bryostatin's susceptibility to rearrangement and hydrolysis has critical implications for its medicinal applications.
Understanding these degradation pathways is crucial for optimizing bryostatin extraction and formulation.