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Related Concept Videos

Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

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

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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.
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Esters to β-Ketoesters: Claisen Condensation Overview01:24

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Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
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Types of Step-Growth Polymers: Polyesters01:20

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The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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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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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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

Updated: Sep 22, 2025

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers
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Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers

Published on: November 22, 2015

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Manufacturing specialized wax esters in plants.

Kamil Demski1, Bao-Jian Ding2, Hong-Lei Wang2

  • 1Department of Plant Breeding, Swedish University of Agricultural Sciences, Box 190, 23422, Lomma, Sweden.

Metabolic Engineering
|May 22, 2022
PubMed
Summary

This study demonstrates the successful in planta production of valuable wax esters, including spermaceti-like biolubricants and insect pheromone components, using synthetic biology in plants.

Keywords:
Insect sex pheromonesPest controlPlant factorySpermacetiSynthetic biologyWax esters

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Last Updated: Sep 22, 2025

Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers
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Area of Science:

  • Synthetic biology
  • Plant biotechnology
  • Biochemistry

Background:

  • Biologically produced wax esters have diverse industrial applications, including biolubricants and insect pheromones.
  • Historical overharvesting of sperm whales for spermaceti created a market need for sustainable alternatives.
  • Insect pheromones are crucial for pest management strategies, offering an eco-friendly alternative to pesticides.

Purpose of the Study:

  • To investigate the feasibility of producing specific wax esters in plants via transient gene expression.
  • To engineer plant lipid metabolism for the synthesis of wax esters with targeted fatty acyl and fatty alcohol moieties.
  • To explore the production of insect pheromone-like compounds in plants.

Main Methods:

  • Transient expression of various gene combinations in Nicotiana benthamiana leaves.
  • Utilizing synthetic biology designs to redirect plant lipid metabolism.
  • Employing plant codon-optimized moth acyl-CoA desaturases for unsaturated moiety production.

Main Results:

  • Successful production of industrially relevant spermaceti-like wax esters enriched in medium-chain fatty acyl and/or fatty alcohol moieties.
  • Generation of wax esters containing unusual, unsaturated fatty alcohol and fatty acyl moieties similar to moth pheromones.
  • Identification of key genetic targets and potential bottlenecks for future stable transformation.

Conclusions:

  • Plants can be engineered to produce valuable wax esters for industrial applications.
  • This approach offers a sustainable alternative to traditional sources of wax esters and a novel method for producing insect pheromones.
  • Further research can optimize gene expression and metabolic pathways for enhanced accumulation of specialized wax esters.