Application Notes:
This 3-hydroxyundecanoic acid methyl ester is a high purity standard that is ideal for analysis and biological systems. 3-
Hydroxyundecanoic acid is unusual in many biological systems and is therefore useful as an internal standard.1 However 3-
hydroxyundecanoic acid is a major constituent of some organisms such as in Idiomarina loihiensis where it is concentrated in
the membrane.2 3-Hydroxy fatty acids are intermediates in fatty acid biosynthesis and have been found to be converted to the
omega-fatty acid by the enzyme CYP4F11 and then into dicarboxylic acids in vivo.3 3-Hydroxy fatty acids are used as
biomarkers for fatty acid oxidative disorders of both the long- and short-chain 3-hydroxy-acyl-CoA dehydrogenases.4
Polyhydroxyalkenoates, polyesters produced by bacteria fermentation, are used for carbon and energy storage and are of
interest in studies regarding their synthesis, properties and mechanisms and are used as biodegradable plastics.5 Medium
chain-length polyhydroxyalkenoate monomers may have pharmaceutical properties.
References:
1. H. Lind et al. “Antifungal compounds from cultures of dairy propionibacteria type strains” FEMS Microbiology Letters, vol. 271 pp. 310-315, 2007
2. S. Hou et al. “Genome sequence of the deep-sea gamma-proteobacterium Idiomarina loihiensis reveals amino acid fermentation as a source of carbon and energy” PNAS, vol. 101 pp. 18036-18041, 2004
3. M. Dhar et al. “Omega-oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11” Journal of Lipid Research, vol. 49, pp. 612-624, 2008
4. P. Jones et al. “Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid” Clinical Chemistry, vol. 47(7) pp. 1190-1194, 2001
5. J. Gangoiti et al. “Production of Chiral (R)-3-Hydroxyoctanoic Acid Monomers, Catalyzed by Pseudomonas fluorescens GK13 Poly(3-Hydroxyoctanoic Acid) Depolymerase” Applied and Environmental Microbiology, vol. 76 pp. 3554-3560, 2010