2-Hydroxyhexadecanoic acid

2-Hydroxy fatty acids are abundant in nervous tissues and are components of cerebrosides and sulfatides, which are mostly found in the myelin of nervous tissues. They are common in cosmetics, skin creams, and lotions. 2-hydroxy acids display complex monolayer phase behavior due to the additional hydrogen bonding afforded by the presence of the second hydroxy group and therefore play an important role in the membrane structure.1 2-Hydroxyhexadecanoic acid is formed by the oxidation of hexadecanoic acid by the enzyme fatty acid 2-hydroxylase. This enzyme is also responsible for the formation of 2-hydroxy galactolipids in the peripheral nervous system.2 alpha-Oxidation of 2-hydroxy fatty acids to CO2 and saturated acids occurs in the peroxisome and is unique from the alpha-oxidation of beta-carbon branched fatty acids such as phytanic acid. Cells from Zellweger syndrome and peroxisome-deficient cells are unable to undergo alpha-oxidation although patients with other peroxisomal disorders such as X-linked adrenoleukodystrophy, Refsum disease, and rhizomelic chondrodysplasia punctata are able.3 Fumonisin B1, a sphingolipid-like toxin found in molds, enhances the accumulation of sphingolipids and 2-hydroxy fatty acids while decreasing the amount of trihydroxy fatty acids.4