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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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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...
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Oxidation of Alcohols02:37

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Radical Autoxidation01:20

Radical Autoxidation

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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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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.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Effect of Polyphenol Oxidase on Deodorization.

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|July 12, 2016
PubMed
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Polyphenol oxidases (PPO) and polyphenolic compounds (PPs) effectively eliminate methylmercaptan odors by rapidly reacting with odor compounds. This oxidation process shows promise for removing bad smells from the mouth and environment.

Keywords:
2-methylthiochlorogenic aciddeodorizationperoxidasepolyphenol oxidasepolyphenolic compound

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Area of Science:

  • Biochemistry
  • Food Science
  • Environmental Science

Background:

  • Methylmercaptan is a volatile sulfur compound responsible for unpleasant odors.
  • Polyphenol oxidases (PPO) are enzymes that catalyze the oxidation of phenolic compounds.
  • Polyphenolic compounds (PPs) are widely found in fruits and vegetables.

Purpose of the Study:

  • To investigate the efficacy of polyphenol oxidases (PPO) and polyphenolic compounds (PPs) in eliminating methylmercaptan odor.
  • To elucidate the reaction mechanism between PPO-generated o-quinones and methylmercaptan.

Main Methods:

  • Using purified PPO or acetone powders from fruits/vegetables with PPs.
  • Reacting the mixture with methylmercaptan and analyzing the products using chromatography and spectroscopy.
  • Isolating and identifying reaction byproducts like methylthiochlorogenic acids.

Main Results:

  • A mixture of PPO and PPs completely eliminated methylmercaptan odor.
  • 2-Methyl-thiochlorogenic acid was isolated from the reaction mixture.
  • Formation of 5-methylthiochlorogenic acid and 2,5-bis(methylthio)-chlorogenic acid was suggested.
  • o-Quinone compounds formed from o-diphenols by PPO rapidly reacted with methylmercaptan.

Conclusions:

  • PPO-mediated oxidation of PPs effectively neutralizes methylmercaptan odor.
  • The reaction involves rapid addition of methylmercaptan to PPO-generated o-quinones.
  • This enzymatic oxidation offers a potential strategy for deodorization in oral care and environmental applications.