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Related Concept Videos

Esters to Carboxylic Acids: Saponification01:25

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...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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 Synthesis01:14

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.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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.

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Related Experiment Video

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Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis
09:26

Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis

Published on: November 17, 2011

The effect of esterases on 17alpha-hydroxyprogesterone caproate.

Ru Yan1, Valentina Fokina, Gary D V Hankins

  • 1Department of Obstetrics & Gynecology, University of Texas Medical Branch, Galveston, TX, USA.

American Journal of Obstetrics and Gynecology
|October 16, 2007
PubMed
Summary

17alpha-hydroxyprogesterone caproate is not hydrolyzed by esterase enzymes in human plasma, liver, or placenta. This in vitro study found no evidence of hydrolysis to 17alpha-hydroxyprogesterone and caproate.

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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
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Area of Science:

  • Pharmacology and Toxicology
  • Biochemistry
  • Drug Metabolism

Background:

  • 17alpha-hydroxyprogesterone caproate is a synthetic progestogen.
  • Understanding its metabolic fate is crucial for clinical applications.
  • Hydrolysis by esterases is a potential metabolic pathway.

Purpose of the Study:

  • To investigate the in vitro hydrolysis of 17alpha-hydroxyprogesterone caproate.
  • To determine if hydrolysis occurs to 17alpha-hydroxyprogesterone and caproate.
  • To assess the role of human plasma, liver, and placental esterases.

Main Methods:

  • Dual radioactively labeled 17alpha-hydroxy-[3H] progesterone [14C] caproate was used.
  • Incubation with human plasma, hepatic S9, placental S9, and recombinant esterases.
  • High-performance liquid chromatography with online radioactivity detection analyzed for hydrolysis products.

Main Results:

  • Human plasma, hepatic, and placental S9 fractions demonstrated esterase activity with prototypic substrates.
  • No detectable [3H]-17alpha-hydroxyprogesterone or [14C]-caproate was formed.
  • 17alpha-hydroxyprogesterone caproate remained intact under experimental conditions.

Conclusions:

  • 17alpha-hydroxyprogesterone caproate is resistant to hydrolysis by major human esterase enzymes in vitro.
  • This suggests alternative metabolic pathways or limited biotransformation via esterase hydrolysis.
  • Findings have implications for the pharmacokinetics and efficacy of 17alpha-hydroxyprogesterone caproate.