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Chemical Compound Review

Myristate     tetradecanoic acid

Synonyms: Crodacid, myristoate, Myristinsaeure, Tetradecanoate, Neo-fat 14, ...
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Disease relevance of tetradecanoic acid


High impact information on tetradecanoic acid


Biological context of tetradecanoic acid

  • The acylation pattern at the 'reducing' GlcN I was identical to that of compound 406 in having two primary (R)-3-hydroxy tetradecanoic acid residues [14:0(3-OH)] attached to positions 3 (ester-linked) and 2 (amide-linked), respectively [10].

Anatomical context of tetradecanoic acid


Associations of tetradecanoic acid with other chemical compounds

  • A diterpene of the ingenane-type parent alcohol with tetradecanoic acid as the acid substituent was isolated by chromatographic methods from the latex of Euphorbia matabelensis [13].
  • The purified product, methyl-3-0-(9-carboxy-anthracenyl) tetradecanoate (M/Z 462), was highly responsive to a fluorescence spectrophotometer, showing maximum emission with excitation wavelength at 257 nm and emission wavelength at 458 nm in dichloromethane, the limit of detection being as little as 10 f mol [14].
  • Comparison of the amount of [3H]aldehyde produced with the bioluminescence responses of luciferase to the aldehyde product and standard aldehydes, both with respect to maximum light intensity and luminescent decay, established that tetradecanoic acid has been converted to tetradecanal, the aldehyde of the same chain length [15].

Gene context of tetradecanoic acid

  • Highly lipidated C14 HSA (C14, fatty acid side-chains with 14 carbon atoms) was not itself mitogenic: unlike HSA it localized heavily to the red pulp as well as to cells of dendritic form in the splenic white pulp [16].
  • In a subclone missing the lux E gene, the 42 kDa polypeptide was missing and the 54 kDa polypeptide could not be acylated in vitro with tetradecanoic acid (+ATP) and only to a low level in vivo indicating that the synthetase enzyme, responsible for fatty acid activation, is coded by the lux E gene [17].


  1. Tumor promoter and epidermal growth factor stimulate phosphorylation of the c-erbB-2 gene product in MKN-7 human adenocarcinoma cells. Akiyama, T., Saito, T., Ogawara, H., Toyoshima, K., Yamamoto, T. Mol. Cell. Biol. (1988) [Pubmed]
  2. The Pseudomonas aeruginosa lipid A deacylase: selection for expression and loss within the cystic fibrosis airway. Ernst, R.K., Adams, K.N., Moskowitz, S.M., Kraig, G.M., Kawasaki, K., Stead, C.M., Trent, M.S., Miller, S.I. J. Bacteriol. (2006) [Pubmed]
  3. Possible fatty acyl pheromone precursors in Spodoptera littoralis. Search for 11- and 12-hydroxytetradecanoic acids in the pheromone gland. Navarro, I., Fabriàs, G., Camps, F. Lipids (1997) [Pubmed]
  4. Toxicity studies of tetradecanoic acid, 2-sulfo-, 1-methylester, sodium salt (C14-MES). Sato, J., Yamamoto, Y., Nakamura, T., Ishida, S., Takagi, Y. The Journal of toxicological sciences. (2005) [Pubmed]
  5. n-Tetradecanoyl is the NH2-terminal blocking group of the catalytic subunit of cyclic AMP-dependent protein kinase from bovine cardiac muscle. Carr, S.A., Biemann, K., Shoji, S., Parmelee, D.C., Titani, K. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  6. Myristic acid stimulation of bacterial bioluminescence in "aldehyde" mutants. Ulitzur, S., Hastings, J.W. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  7. Isolation and characterization of a murine serum esterase which hydrolyzes a tumor promoter, 12-O-tetradecanoyl phorbol 13-acetate. Saito, M., Egawa, K. J. Biol. Chem. (1984) [Pubmed]
  8. Synthesis of carbon-13-labeled tetradecanoic acids. Sparrow, J.T., Patel, K.M., Morrisett, J.D. J. Lipid Res. (1983) [Pubmed]
  9. Structural characterization of the lipid A of Bordetella pertussis 1414 endotoxin. Caroff, M., Deprun, C., Richards, J.C., Karibian, D. J. Bacteriol. (1994) [Pubmed]
  10. Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes. Zähringer, U., Salvetzki, R., Wagner, F., Lindner, B., Ulmer, A.J. J. Endotoxin Res. (2001) [Pubmed]
  11. Comparative chemical characterization of pigmented and less pigmented cell walls of Alternaria tenuissima. Kishore, K.H., Kanjilal, S., Misra, S., Reddy, C.R., Murty, U.S. Curr. Microbiol. (2005) [Pubmed]
  12. Two modes of irreversible inactivation of the mitochondrial electron-transfer system by tetradecanoic acid. Schewe, T., Albracht, S.P., Ludwig, P., Rapoport, S.M. Biochim. Biophys. Acta (1985) [Pubmed]
  13. A skin irritant principle from Euphorbia matabelensis Pax. Gundidza, M., Sorg, B., Hecker, E. Journal of ethnopharmacology. (1993) [Pubmed]
  14. Development of a new quantitative method for detection of endotoxin by fluorescence labeling of 3-hydroxy fatty acid. Tanamoto, K. Adv. Exp. Med. Biol. (1990) [Pubmed]
  15. Fatty acid reductase in bioluminescent bacteria. Resolution from aldehyde reductases and characterization of the aldehyde product. Riendeau, D., Meighen, E. Can. J. Biochem. (1981) [Pubmed]
  16. Immunogenicity of lipid-conjugated antigens. II. Anti-complementary activity and antigen trapping in the spleen. Stark, J.M., Matthews, N., Locke, J. Immunology (1980) [Pubmed]
  17. Lux C, D and E genes of the Vibrio fischeri luminescence operon code for the reductase, transferase, and synthetase enzymes involved in aldehyde biosynthesis. Boylan, M., Miyamoto, C., Wall, L., Graham, A., Meighen, E. Photochem. Photobiol. (1989) [Pubmed]
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