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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
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Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

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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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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

11.0K
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
11.0K
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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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.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of...
14.0K
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Extraction of Lignin with High &#946;-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield
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Aliphatic phenolic ethers from Trichobotrys effusa.

Jih-Jung Chen1, Shih-Wei Wang, Hui-Yun Hsiao

  • 1Department of Pharmacy, Tajen University , Pingtung, Taiwan 907.

Journal of Natural Products
|May 7, 2014
PubMed
Summary

Four new compounds, trichoethers A-D, were isolated from Trichobotrys effusa. These compounds, along with radicicol, show potential for inhibiting non-small cell lung cancer cell growth.

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • The fungus Trichobotrys effusa is a source of bioactive natural products.
  • Identifying novel compounds with anti-cancer properties is crucial for drug discovery.

Purpose of the Study:

  • To isolate and characterize novel compounds from Trichobotrys effusa.
  • To evaluate the anti-cancer activity of isolated compounds against non-small cell lung cancer.

Main Methods:

  • Isolation of compounds using ethyl acetate extraction from fermented broths.
  • Structure elucidation through comprehensive spectroscopic data analysis (NMR, MS).
  • Determination of stereochemistry using J-coupling values and NOESY experiments.

Main Results:

  • Four novel aliphatic phenolic ethers, trichoethers A-D (1-4), were identified with a unique C11-O-C10 skeleton.
  • Coriloxin, zythiostromic acid A, radicicol, and 3,5-dihydroxytoluene were also isolated.
  • Trichoethers A-D and radicicol demonstrated significant growth inhibition against A549 non-small cell lung cancer cells.
  • GI50 values for trichoethers A-D and radicicol ranged from 1.43 to 25.61 μM, with radicicol showing the most potent activity.

Conclusions:

  • Trichobotrys effusa produces structurally unique phenolic ethers with anti-cancer potential.
  • Radicicol exhibits potent cytotoxic activity against non-small cell lung cancer cells, warranting further investigation.
  • The novel trichoethers represent a new class of compounds with potential therapeutic applications in oncology.