Application Notes:
This product is a high purity 2-hydroxy fatty acid that is ideal as a standard and for biological systems. alpha-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 and skin creams and lotions. 2-Hydroxytetradecanoic acid is
formed by the oxidation of tetradecanoic 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.1 2-Hydroxytetradecanoic acid can form 2-
hydroxymyristoyl-CoA which is a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that
catalyzes protein N-myristoylation, and can be used to reduce the amount of p56lck (a protein-tyrosine kinases) at the plasma
membrane.2 2-Hydroxytetradecanoic acid, but not other 2-hydroxy acids or any 3-hydroxy acids, was found to stimulate an
increase in elongated lateral branches of some fungi.3 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.4
References:
1. C. Lendrum et al. “Nonequilibrium 2-Hydroxyoctadecanoic Acid Monolayers: Effect of Electrolytes” Langmuir, vol. 27 pp. 4430-4438, 2011
2. J. Sjogren et al. “Antifungal 3-Hydroxy Fatty Acids from Lactobacillus plantarum MiLAB 14” Applied and Environmental Microbiology, vol. 69 pp. 7554-7557, 2003
3. G. Nagahashi and D. Douds Jr. “The effects of hydroxy fatty acids on the hyphal branching of germinated spores of AM fungi” Fungal Biology, vol. 115 pp. 351-358, 2011
4. R. Sandhir, M. Khan, and I. Singh “Identification of the Pathway of alpha-Oxidation of Cerebronic Acid in Peroxisomes” Lipids, Vol. 35(10) pp. 1127-1133, 2000