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Related Concept Videos

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 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:
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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.
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.
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

Updated: Jun 5, 2026

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

3β-Hydroxy-friedelan-17β-carboxylic acid.

Hai-Yan Chen, Cui-Wu Lin, Guang-Ying Chen

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    A new friedelan derivative, C(30)H(50)O(3), was discovered in a marine fungus. Its molecular structure features five six-membered rings and is stabilized by intermolecular hydrogen bonds.

    Area of Science:

    • Marine natural products chemistry
    • Organic chemistry
    • Mycology

    Background:

    • Marine endophytic fungi are a rich source of novel bioactive compounds.
    • Friedelane derivatives represent a class of triterpenoids with diverse biological activities.
    • Exploring new chemical entities from marine organisms is crucial for drug discovery.

    Purpose of the Study:

    • To isolate and characterize a new friedelan derivative from a marine endophytic fungus.
    • To elucidate the molecular structure and stereochemistry of the novel compound.
    • To investigate the structural features and intermolecular interactions of the isolated compound.

    Main Methods:

    • Isolation of the compound using chromatographic techniques.
    • Structure elucidation using spectroscopic methods (NMR, MS).

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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

    Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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    Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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    A Strategy for Sensitive, Large Scale Quantitative Metabolomics

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  • X-ray crystallography for determining the crystal structure and conformation.

    • Main Results:

    • A new friedelan derivative, C(30)H(50)O(3), was successfully isolated and identified.
    • The molecule comprises five six-membered rings with specific conformations (boat, distorted boat, chair).
    • Crystal structure analysis revealed intermolecular O-H⋯O hydrogen bonds forming 12-membered rings.

    Conclusions:

    • The discovery of this new friedelan derivative expands the known chemical diversity of marine fungal metabolites.
    • The detailed structural analysis provides insights into the conformational preferences and intermolecular interactions of this compound class.
    • This finding highlights the potential of marine endophytic fungi as a source for novel chemical structures.