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Oxidation of Phenols to Quinones

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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 property is crucial in...

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2-Hydr-oxy-1-methoxy-anthraquinone monohydrate.

Zhi-Meng Liu¹, Yuan-Qi Jiao

¹School of Materials Science and Engineering, South China University of Technology, Guangzhou 510641, People's Republic of China.

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|May 18, 2011

Summary

Alizarin 1-methyl ether monohydrate, isolated from Morinda officinalis, features an anthraquinone structure with a nearly planar ring system. Its crystal structure reveals a 3D network formed by hydrogen bonds between organic and water molecules.

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Area of Science:

Natural Product Chemistry
Crystallography
Organic Chemistry

Background:

Morinda officinalis is a plant source of bioactive compounds.
Anthraquinones are a class of organic compounds with diverse biological activities.
Understanding the crystal structure of natural products aids in elucidating their properties.

Purpose of the Study:

To isolate and characterize alizarin 1-methyl ether monohydrate from Morinda officinalis.
To determine the crystal structure of alizarin 1-methyl ether monohydrate.
To investigate the intermolecular interactions within the crystal lattice.

Main Methods:

Isolation of the title compound from Morinda officinalis.
Single crystal X-ray diffraction analysis to determine the crystal structure.
Analysis of bond lengths, bond angles, and hydrogen bonding patterns.

Main Results:

Alizarin 1-methyl ether monohydrate (C(15)H(10)O(4)·H(2)O) was successfully isolated.
The anthraquinone ring system was found to be nearly planar, with a dihedral angle of 3.07° between the outer benzene rings.
A three-dimensional network was observed, formed by O-H⋯O hydrogen bonds linking the organic molecules and water molecules.

Conclusions:

The crystal structure of alizarin 1-methyl ether monohydrate has been elucidated.
The study provides insights into the solid-state packing and intermolecular interactions of this natural product.
The findings contribute to the understanding of the structural diversity of anthraquinones from Morinda officinalis.