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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...

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

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Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Related Experiment Video

Updated: Dec 5, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

Phenolic glycosides from Oroxylum indicum.

Le Thi Vien¹, Tran Thi Hong Hanh¹, Tran Hong Quang¹

¹Advanced Center for Bio-Organic Chemistry, Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam.

Natural Product Research

|October 20, 2020

Summary

Two novel phenolic glycosides, oroxylumosides A and B, were isolated from *Oroxylum indicum*. Compounds 1-4 demonstrated inhibitory effects on nitric oxide production in a microglial cell line.

Keywords:

Bignoniaceae NO production Oroxylum indicum phenolic glycoside

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Area of Science:

Natural Products Chemistry
Pharmacology
Neuroscience

Background:

*Oroxylum indicum* is a traditional medicinal plant.
Phenolic glycosides are known for their diverse biological activities.
Neuroinflammation plays a key role in various neurological disorders.

Purpose of the Study:

To isolate and characterize new compounds from *Oroxylum indicum* stem bark.
To evaluate the anti-inflammatory potential of isolated compounds in a microglial cell model.

Main Methods:

Isolation and purification of compounds using chromatographic techniques.
Structural elucidation using Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry (HR-ESI-QTOF-MS).
In vitro anti-inflammatory assay measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated BV2 microglial cells.

Main Results:

Two new phenolic glycosides, oroxylumosides A (1) and B (2), were identified.
Four known compounds, darendoside A (3), leucosceptoside A (4), acteoside (5), and decaffeoylacteoside (6), were also isolated.
Compounds 1-4 exhibited inhibitory effects on NO production with IC50 values ranging from 56.8 to 70.6 µM.

Conclusions:

The study successfully identified novel and known phenolic glycosides from *Oroxylum indicum*.
Compounds 1-4 possess anti-inflammatory properties, suggesting potential therapeutic applications for neuroinflammation.