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Oxidation of Phenols to Quinones01:17

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.
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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...
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Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

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Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
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Acidity and Basicity of Alcohols and Phenols02:36

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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Novel Phenolic Constituents of

Justyna Krzyżanowska-Kowalczyk1, Łukasz Pecio2, Jarosław Mołdoch3

  • 1Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation-State Research Institute, Czartoryskich 8, 24-100 Puławy, Poland. jkrzyzanowska@iung.pulawy.pl.

Molecules (Basel, Switzerland)
|September 12, 2018
PubMed
Summary

Lungwort, a traditional herbal remedy for lung disorders, has a complex phytochemical profile. This study identified nine new phenolic compounds, expanding our understanding of its medicinal potential.

Keywords:
CDHR-QTOF/MSNMRPulmonaria officinalisPulmonariae Herbadanshensu/caffeic acid/rosmarinic acid derivativeslungwortmetabolite profilingmultivariate analysesseasonal variability

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Area of Science:

  • Phytochemistry
  • Pharmacognosy
  • Natural Product Chemistry

Background:

  • Lungwort (Pulmonaria officinalis L.) is traditionally used for lung ailments.
  • Limited data exists on its specific phytochemical composition.
  • Understanding its chemical constituents is crucial for validating traditional uses.

Purpose of the Study:

  • To comprehensively characterize the specialized metabolites in the aerial parts of Lungwort.
  • To identify and determine the structures of novel compounds.
  • To quantify identified phenolic compounds and investigate seasonal variations.

Main Methods:

  • Extraction of aerial parts using 50% methanol.
  • Multistep preparative isolation techniques.
  • Structure elucidation using 1D and 2D NMR spectroscopy.
  • Quantification via liquid chromatography-high-resolution mass spectrometry (LC-HRMS).
  • Metabolomic analysis for seasonal variations.

Main Results:

  • Nine previously undescribed and 36 known phenolic compounds were identified.
  • Identified compounds include caffeic acid esters, dicaffeic acid conjugates, lignans, and novel isomers.
  • Concentrations of phenolic derivatives were quantified.
  • Seasonal variations in metabolite profiles were observed.

Conclusions:

  • The study provides a detailed phytochemical profile of Lungwort, revealing novel compounds.
  • This research contributes to the scientific validation of Lungwort's traditional therapeutic applications.
  • Further investigation into the bioactivity of identified compounds is warranted.