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The reaction of formaldehyde with unsaturated fatty acids during histological fixation

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Formaldehyde reacts with unsaturated fatty acids in tissues during histological fixation. The reaction of formaldehyde with oleic acid has been found to given rise to compounds (adducts) with the following structures:

Two other compounds were isolated but their nature is still open to doubt.

The equilibrium constant for the initial part of the reaction has been approximately estimated as 0·042 at a room temperature of 22°C. The endothermic heat of reaction has been estimated as approximately 12·6 kcal.

The occurrence of these adducts in tissues explains why it is that less lipid can be demonstrated histologically in material that has been stored in form-aldehyde for a considerable length of time.

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Jones, D. The reaction of formaldehyde with unsaturated fatty acids during histological fixation. Histochem J 1, 459–491 (1969). https://doi.org/10.1007/BF01086985

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  • Lipid
  • Adduct
  • Equilibrium Constant
  • Unsaturated Fatty Acid
  • Initial Part