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Aromatic Compounds: Overview

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...

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...

Organic Compounds

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...

Nomenclature of Aromatic Compounds with Multiple Substituents

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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.

Preparation of Diols and Pinacol Rearrangement

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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.

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Phenolics from Lagotis brevituba Maxim.

Xiang Yuan^1,2, Huaixiu Wen^1,2, Yulei Cui^1,2

¹a Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology , Chinese Academy of Sciences , Xining , P.R. China.

Natural Product Research

|October 5, 2016

Summary

This study identified 11 phenolic compounds from Lagotis brevituba, with protocatechuic acid and luteolin showing significant antioxidant activity superior to rutin. Several compounds were novel to the Lagotis genus.

Keywords:

Lagotis brevituba phenolics spectroscopic methods

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Area of Science:

Phytochemistry
Natural Product Chemistry
Pharmacognosy

Background:

Lagotis brevituba is a plant species with potential medicinal properties.
Phenolic compounds are known for their diverse biological activities, including antioxidant effects.

Purpose of the Study:

To isolate and characterize phenolic compounds from Lagotis brevituba.
To evaluate the antioxidant potential of the isolated compounds.

Main Methods:

Phytochemical investigation involving isolation and spectroscopic characterization of compounds.
Antioxidant activity assessment using DPPH and ABTS radical scavenging assays.

Main Results:

Eleven phenolic compounds were identified, including nine new to L. brevituba and six new to the Lagotis genus.
Protocatechuic acid (4) and luteolin (11) exhibited potent antioxidant activity against DPPH radical, outperforming the positive control rutin.
Luteolin (11) also demonstrated superior ABTS radical scavenging activity compared to rutin.

Conclusions:

Lagotis brevituba is a rich source of diverse phenolic compounds.
Protocatechuic acid and luteolin possess significant antioxidant properties, suggesting their potential therapeutic applications.