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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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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...
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Structures of Aldehydes and Ketones01:04

Structures of Aldehydes and Ketones

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Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the...
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
4.0K
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

4.7K
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction01:25

Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction

2.8K
The Cannizzaro reaction is a base-promoted redox reaction producing a primary alcohol and a carboxylic acid from two molecules of a nonenolizable aldehyde. The reaction commences when the anionic counterpart of the base attacks the carbonyl carbon, resulting in a tetrahedral alkoxide intermediate. The base then abstracts a proton from the intermediate to generate an unstable dianionic species. This intermediate enables the release of the aldehydic hydrogen as a hydride ion. An intermolecular...
2.8K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.1K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Three new compounds from Cinnamomum cassia.

Shan He1, Yong Jiang1, Peng-Fei Tu1

  • 1a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191 , China.

Journal of Asian Natural Products Research
|October 27, 2015
PubMed
Summary

Researchers isolated new diterpenoids and phenolic glycosides from Cinnamomum cassia bark. These compounds exhibited weak anti-inflammatory activity in microglial cell assays.

Keywords:
Cinnamomum cassiaanti-inflammatory activitychemical constituentsditerpenoidshydroxylasiodiplodin

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Cinnamomum cassia (cassia bark) is a traditional medicinal herb.
  • Diterpenoids and phenolic glycosides are classes of natural compounds with diverse biological activities.
  • Understanding the chemical constituents of C. cassia is important for its medicinal applications.

Purpose of the Study:

  • To isolate and characterize new and known compounds from Cinnamomum cassia bark.
  • To evaluate the anti-inflammatory potential of the isolated compounds.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation through extensive spectroscopic analysis (e.g., NMR, MS).
  • In vitro anti-inflammatory assay using lipopolysaccharide-induced BV-2 microglial cells to measure nitric oxide production.

Main Results:

  • Three new compounds were identified: two diterpenoids (epianhydrocinnzeylanol and cinnacasiol H) and one hydroxylasiodiplodin derivative.
  • Five known diterpenoids and two known phenolic glycosides were also isolated.
  • The isolated compounds demonstrated weak inhibitory activity against nitric oxide production in BV-2 microglial cells.

Conclusions:

  • The chemical investigation of Cinnamomum cassia bark led to the discovery of novel diterpenoids.
  • While the isolated compounds showed anti-inflammatory properties, their activity was weak in this specific assay.
  • Further research may be needed to explore the therapeutic potential of these compounds or their derivatives.