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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

4.8K
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...
4.8K
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

22.5K
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...
22.5K
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

16.8K
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.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
16.8K
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

22.2K
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.
22.2K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

4.0K
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...
4.0K
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

4.3K
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...
4.3K

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Anticancer Phenolics from Dryopteris fragrans (L.) Schott.

Zhen-Dong Liu1, Dan-Dan Zhao2, Shuai Jiang3

  • 1Key Laboratory of Saline-alkali Vegetation Ecology Restoration, Ministry of Education/Alkali Soil Natural Environmental Science Center, Northeast Forestry University, Harbin 150040, China. liu304418091@126.com.

Molecules (Basel, Switzerland)
|March 23, 2018
PubMed
Summary

Researchers isolated a novel anticancer molecule from the medicinal plant *D. fragrans*. This compound showed significant efficacy against breast cancer cells, offering new hope for cancer treatment strategies.

Keywords:
Dryopteris fragrans (L.) SchottFragranoside Banticancer activity

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Plant Research

Background:

  • Cancer remains a significant global health threat, necessitating the discovery of novel therapeutic agents.
  • Medicinal plants are a rich source of diverse chemical compounds with potential pharmacological activities.
  • Daphne fragrans (D. fragrans) is a plant with traditional medicinal uses, warranting investigation for its bioactive constituents.

Purpose of the Study:

  • To isolate and characterize novel anticancer compounds from D. fragrans.
  • To evaluate the cytotoxic effects of isolated compounds against various human cancer cell lines.

Main Methods:

  • Phytochemical analysis of D. fragrans using spectroscopic techniques (¹H-NMR, ¹³C-NMR, 2D NMR) for structure elucidation.
  • Anticancer activity assessment via the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay.
  • Testing against human lung (A549), breast (MCF-7), and gastric (SGC7901) cancer cells, alongside noncancerous human umbilical vein endothelial cells (HUVEC).

Main Results:

  • A new phenylpropanoid glycoside, (E)-caffeic acid-9-O-β-d-xylpyranosyl-(1→2)-β-d-glucopyranosyl ester (compound 1), was successfully isolated and identified.
  • Compound 1 exhibited potent cytotoxicity against MCF-7 breast cancer cells with an IC50 value of 2.65 ± 0.14 µM.
  • Seven known compounds (2-8) were also isolated, with compound 8 demonstrating IC50 values below 20 µM against three tested cancer cell lines.

Conclusions:

  • D. fragrans is a valuable source of bioactive compounds with significant anticancer potential.
  • The novel phenylpropanoid glycoside (compound 1) shows promising selective cytotoxicity against breast cancer cells.
  • Further research into these compounds could lead to the development of new anticancer therapeutics.