Omega Hydroxy Fatty Acids and Methyl Esters

omega-Hydroxy fatty acids are produced by omega-oxidation and can be lactonized by certain enzymes into mono- and oligolactones.1,2 Stimulation of omega-hydroxylation has been proposed as a method for treating X-linked adrenoleukodystrophy, a disease that is characterized by elevated levels of very long chain fatty acids.3 omega-Hydroxylated very long chain fatty acid ceramides are vital to skin barrier functions and a deficiency of these lipids can cause death from water loss through the skin. In atopic dermatitis, a common skin disease, there are considerable deficiencies of omega-hydroxy long chain fatty acids acylated to ceramides and this may contribute to the severely damaged permeability barrier.4

References:

  1. M. Nakano, E. Kelly, and A. Rettie “Expression and Characterization of CYP4V2 as a Fatty Acid ω-Hydroxylase” Drug Metabolism and Disposition, vol. 37 pp. 2119-2122, 2009
  2. U. Antczak et al. “Enzymatic lactonization of 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic acids to macrocyclic lactones” Enzyme and Microbial Technology, vol. 13 pp. 589-593, 1991
  3. R. Sanders et al. “Omega-Oxidation of Very Long-Chain Fatty Acids in Human Liver Microsomes: Implications for X-Linked Adrenoleukodystrophy” Journal of Biological Chemistry, Vol. 281 pp. 13180-13187, 2006
  4. O. Macheleidt, H. Kaiser, K. Sandhoff “Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis” J Invest Dermatol., vol. 119 pp. 166-173, 2002

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22-Hydroxydocosanoic acid

Methyl 22-hydroxydocosanoate

Methyl 27-hydroxyheptacosanoate