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Oxidation of Phenols to Quinones

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...

Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Structure and Nomenclature of Alcohols and Phenols

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and...

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

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Semi-Targeted Ultra-High-Performance Chromatography Coupled to Mass Spectrometry Analysis of Phenolic Metabolites in Plasma of Elderly Adults

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Phenolic compounds from Limonium pruinosum.

Sihem Boudermine, Nicola Malafronte, Teresa Mencherini

Natural Product Communications

|April 30, 2015

Summary

Researchers identified a novel phenolic compound, 6'-O-sulfonyl-salidroside, from Limonium pruinosum. The study also evaluated the antioxidant potential of this compound and others isolated from the plant using the DPPH test.

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Published on: June 10, 2022

Area of Science:

Phytochemistry
Natural Products Chemistry
Pharmacognosy

Background:

Limonium pruinosum is a plant species with potential medicinal properties.
Phenolic compounds are known for their diverse biological activities, including antioxidant effects.
Isolation and characterization of novel compounds from natural sources are crucial for drug discovery.

Purpose of the Study:

To isolate and identify compounds from Limonium pruinosum.
To characterize a new phenolic compound, 6'-O-sulfonyl-salidroside.
To evaluate the antioxidant activity of the isolated compounds and plant extracts.

Main Methods:

Phytochemical investigation of Limonium pruinosum using various chromatographic techniques.
Structure elucidation of isolated compounds utilizing 1D and 2D NMR (1D TOCSY, DQF-COSY, HSQC, HMBC) and ESIMS.
Antioxidant activity assessment using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.

Main Results:

A new phenolic compound, 6'-O-sulfonyl-salidroside (1), was isolated and characterized.
Fifteen known compounds were also isolated from the plant.
The antioxidant activity of the extracts and all isolated compounds was evaluated.

Conclusions:

The study successfully identified a new phenolic compound from Limonium pruinosum.
The findings contribute to the understanding of the chemical constituents of this plant species.
Further research may explore the pharmacological potential of the isolated compounds, particularly their antioxidant properties.