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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Radical Autoxidation01:20

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...

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Related Experiment Video

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Original Experimental Approach for Assessing Transport Fuel Stability
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Original Experimental Approach for Assessing Transport Fuel Stability

Published on: October 21, 2016

Oxidative stability of tree nut oils.

Homan Miraliakbari1, Fereidoon Shahidi

  • 1Department of Biochemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada.

Journal of Agricultural and Food Chemistry
|May 23, 2008
PubMed
Summary

Chloroform/methanol extraction yielded more oil from tree nuts than hexane. Chloroform/methanol-extracted oils, particularly pecan and pistachio, showed greater oxidative stability than hexane-extracted oils.

Area of Science:

  • Food Science
  • Lipid Chemistry
  • Nutritional Biochemistry

Background:

  • Tree nut oils are valuable sources of fatty acids and tocopherols.
  • Oxidative stability is crucial for the shelf-life and quality of edible oils.
  • Understanding factors influencing oil stability is important for food processing and product development.

Purpose of the Study:

  • To evaluate the oxidative stability of various tree nut oils.
  • To compare the effects of different solvent extraction methods (hexane vs. chloroform/methanol) on oil yield and stability.
  • To analyze the fatty acid and tocopherol profiles of the selected tree nut oils.

Main Methods:

  • Extraction of oils from almond, Brazil nut, hazelnut, pecan, pine nut, pistachio, and walnut using hexane and chloroform/methanol.

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Evaluation of Oxidative Stress in Biological Samples Using the Thiobarbituric Acid Reactive Substances Assay
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Evaluation of Oxidative Stress in Biological Samples Using the Thiobarbituric Acid Reactive Substances Assay

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  • Gas chromatography (GC) for fatty acid composition analysis.
  • High-performance liquid chromatography (HPLC) for tocopherol composition analysis.
  • Accelerated autoxidation and photooxidation studies to assess oxidative stability.
  • Monitoring oxidation progression via conjugated dienes, peroxide value, p-anisidine value, and headspace volatiles.

    • Main Results:

    • Chloroform/methanol extraction yielded higher oil quantities compared to hexane extraction.
    • Oleic acid was predominant in most oils, except pine nut and walnut, which were rich in linoleic acid.
    • Alpha- and gamma-tocopherols were the major tocopherols, with delta- and beta-tocopherols also detected.
    • Chloroform/methanol-extracted oils exhibited superior oxidative stability under both autoxidation and photooxidation conditions.
    • Pecan and pistachio oils demonstrated the highest oxidative stability, while pine nut and walnut oils were the least stable.

    Conclusions:

    • Solvent extraction method significantly impacts oil yield and oxidative stability.
    • Tree nut oil composition, particularly fatty acid profile, influences oxidative stability.
    • Pecan and pistachio oils are promising candidates for applications requiring high oxidative stability.