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Related Concept Videos

Preparation of Carboxylic Acids: Overview01:31

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.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

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.
Reactions of Carboxylic Acids: Introduction01:41

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.
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

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.

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Related Experiment Video

Updated: May 15, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

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Published on: February 16, 2018

Bioactive carboxylic acids from Lysimachia clethroides.

Dong Liang1, Zhi-You Hao, Yan-Fei Liu

  • 1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.

Journal of Asian Natural Products Research
|January 18, 2013
PubMed
Summary

Researchers isolated six new carboxylic acids from Lysimachia clethroides. Five of these compounds showed in vitro inhibitory activity against aldose reductase, suggesting potential therapeutic applications.

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Pharmacognosy

Background:

  • Lysimachia clethroides is a plant species with potential medicinal properties.
  • Carboxylic acids are a class of organic compounds with diverse biological activities.
  • Aldose reductase is an enzyme implicated in diabetic complications.

Purpose of the Study:

  • To isolate and characterize new carboxylic acids from Lysimachia clethroides.
  • To evaluate the in vitro inhibitory activity of the isolated compounds against aldose reductase.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation using spectroscopic methods (NMR, MS) and chemical evidence.
  • In vitro enzyme inhibition assays against aldose reductase.

Main Results:

  • Six new carboxylic acids (compounds 1-6) were identified, along with 11 known carboxylic acids (compounds 7-17).
  • Five of the newly isolated carboxylic acids (1 and 3-6) demonstrated in vitro inhibitory activity against aldose reductase.
  • The structures of the new compounds were confirmed through comprehensive spectroscopic and chemical analyses.

Conclusions:

  • Lysimachia clethroides is a source of novel carboxylic acids.
  • The new carboxylic acids, particularly compounds 1 and 3-6, exhibit potential as aldose reductase inhibitors.
  • Further investigation into these compounds may lead to the development of new therapeutic agents for managing diabetic complications.