Synthesis of dihydroperoxides of linoleic and linolenic acids and studies on their transformation to 4-hydroperoxynonenal

No abstract is available for this paper.

• Publication year

  2005

• Venue

  Lipids

• Publication date

  2005-11-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1007/s11745-005-1480-3PMID 16459928
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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  1991cited by this paper
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• Identification of 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids.

  1980cited by this paper
• The reaction of singlet oxygen with olefins: the question of mechanism

  1979influential reference
• A rapid method of total lipid extraction and purification.

  1959cited by this paper

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  2017cites this paper
• Lipid peroxidation in cell death.

  2017cites this paper
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  2016cites this paper
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  2015cites this paper
• Microkinetic modeling of the autoxidative curing of an alkyd and oil-based paint model system

  2015cites this paper
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  2015cites this paper
• Microkinetic modeling of the autoxidative curing of an alkyd and oil-based paint model system

  2015cites this paper
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• The dynamics of giant unilamellar vesicle oxidation probed by morphological transitions.

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  2013cites this paper
• Lipid Peroxidation and Nitration

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• Chemical alterations taken place during deep-fat frying based on certain reaction products: a review.

  2012cites this paper
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