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Chemical Compound Review

Pelargon     nonanoic acid

Synonyms: Nonanoate, pergonate, NoEthaCoEa, nonans, Nonansaeure, ...
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Disease relevance of nonanoic acid


High impact information on nonanoic acid


Chemical compound and disease context of nonanoic acid


Biological context of nonanoic acid


Anatomical context of nonanoic acid

  • This study examined Langerhans cell (LC) density in clinically normal skin of 46 patients with chronic ICD and 10 healthy individuals, and compared the action of the two irritants nonanoic acid (NA) and sodium lauryl sulphate (SLS) on the LCs and keratinocytes of clinically normal skin in patients with chronic ICD [18].
  • The extent of nonanoic acid deposition in liver triglycerides, liver phospholipids, adipose tissue and skeletal muscle after C9TG/LCT administration was similar to C8/C10 deposition in the MCT/LCT group; the enrichment of adipose tissue with 16 mol% was higher than expected [19].
  • The photoreactive omega-diazirinophenoxy derivatives of nonanoate, undecanoate, tridecanoate, and pentadecanoate were shown to be activated by rat liver microsomes to the corresponding acyl-CoA derivatives [20].

Associations of nonanoic acid with other chemical compounds


Gene context of nonanoic acid

  • When HNE was quantitated by selective ion monitoring, with reference to a pure standard of HNE and an internal standard of nonanoic acid, ARDS patients showed significantly increased levels of HNE (0.412 +/- 0.023 nmol/ml) compared with normal healthy controls (0.205 +/- 0.018 nmol/ml) [25].
  • The resulting nonanoic acid was also subjected to the action of acyl-CoA oxidase [26].
  • Further, a ligand specific for beta 2-GPI, oxLig-1, purified from the extracted lipids of oxLDL was identified as 7-ketocholesterol-9-carboxynonanoate (i.e., 9-oxo-9-(7-ketocholest-5-en-3 beta-yloxy) nonanoic acid) OxLig-1 was recognized by beta 2-GPI and subsequently by anti-beta 2-GPI autoantibodies [27].

Analytical, diagnostic and therapeutic context of nonanoic acid


  1. Analysis of fatty acids of the genus Rochalimaea by electron capture gas chromatography: detection of nonanoic acid. Westfall, H.N., Edman, D.C., Weiss, E. J. Clin. Microbiol. (1984) [Pubmed]
  2. Protective effect of capsinoid on lipid peroxidation in rat tissues induced by Fe-NTA. Rosa, A., Deiana, M., Corona, G., Atzeri, A., Incani, A., Appendino, G., Dessì, M.A. Free Radic. Res. (2005) [Pubmed]
  3. Nonanoic acid--an experimental irritant. Wahlberg, J.E., Lindberg, M. Contact Derm. (2003) [Pubmed]
  4. Corneocyte morphology and formation rate in lichen planus and experimental parakeratosis in subjects with and without psoriasis. Johannesson, A., Hammar, H. Acta Derm. Venereol. (1982) [Pubmed]
  5. Nonanoic acid irritation - a positive control at routine patch testing? Wahlberg, J.E., Maibach, H.I. Contact Derm. (1980) [Pubmed]
  6. Affinity labeling fatty acyl-CoA synthetase with 9-p-azidophenoxy nonanoic acid and the identification of the fatty acid-binding site. Black, P.N., DiRusso, C.C., Sherin, D., MacColl, R., Knudsen, J., Weimar, J.D. J. Biol. Chem. (2000) [Pubmed]
  7. Differential patterns of epidermal leukocyte infiltration in patch test reactions to structurally unrelated chemical irritants. Willis, C.M., Stephens, C.J., Wilkinson, J.D. J. Invest. Dermatol. (1993) [Pubmed]
  8. Differential effects of structurally unrelated chemical irritants on the density and morphology of epidermal CD1+ cells. Willis, C.M., Stephens, C.J., Wilkinson, J.D. J. Invest. Dermatol. (1990) [Pubmed]
  9. Biotin transport through the blood-brain barrier. Spector, R., Mock, D. J. Neurochem. (1987) [Pubmed]
  10. Cutaneous responses to 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE). Dowd, P.M., Kobza Black, A., Woollard, P.M., Camp, R.D., Greaves, M.W. J. Invest. Dermatol. (1985) [Pubmed]
  11. Do cool water or physiologic saline compresses enhance resolution of experimentally-induced irritant contact dermatitis? Levin, C.Y., Maibach, H.I. Contact Derm. (2001) [Pubmed]
  12. Biosynthesis of polyhydroxyalkanoate copolyester containing cyclohexyl groups by Pseudomonas oleovorans. Kim, D.Y., Jung, S.B., Choi, G.G., Kim, Y.B., Rhee, Y.H. Int. J. Biol. Macromol. (2001) [Pubmed]
  13. Seasonal variation of skin resistance to irritants. Agner, T., Serup, J. Br. J. Dermatol. (1989) [Pubmed]
  14. Antioxidant activity of capsinoids. Rosa, A., Deiana, M., Casu, V., Paccagnini, S., Appendino, G., Ballero, M., Dessí, M.A. J. Agric. Food Chem. (2002) [Pubmed]
  15. Assessment of irritant skin reactions using electrical impedance--a comparison between 2 laboratories. Kuzmina, N., Duval, C., Johnsson, S., Boman, A., Lindberg, M., Emtestam, L. Contact Derm. (2003) [Pubmed]
  16. A new principle of injectable depot contraceptives. I Drug selection and studies in monkeys. Hümpel, M., Schulze, P.E., Speck, U. Contraception. (1979) [Pubmed]
  17. Formulation and in vitro evaluation of transdermal patches of melatonin. Kanikkannan, N., Andega, S., Burton, S., Babu, R.J., Singh, M. Drug development and industrial pharmacy. (2004) [Pubmed]
  18. Epidermal Langerhans cell apoptosis is induced in vivo by nonanoic acid but not by sodium lauryl sulphate. Forsey, R.J., Shahidullah, H., Sands, C., McVittie, E., Aldridge, R.D., Hunter, J.A., Howie, S.E. Br. J. Dermatol. (1998) [Pubmed]
  19. Organ changes after intravenous trinonanoin administration in rabbits. Linseisen, J., Wolfram, G. Ann. Nutr. Metab. (1993) [Pubmed]
  20. Biosynthetic utilization of photoreactive fatty acids by rat liver microsomes. Leblanc, P., Gerber, G.E. Can. J. Biochem. Cell Biol. (1984) [Pubmed]
  21. Effect of fatty acids on the permeation of melatonin across rat and pig skin in-vitro and on the transepidermal water loss in rats in-vivo. Kandimalla, K., Kanikkannan, N., Andega, S., Singh, M. J. Pharm. Pharmacol. (1999) [Pubmed]
  22. Lipolytic and esterolytic activities in posterior lingual glands of rat: a histochemical study. Triantafyllou, A., Fletcher, D., Scott, J. Histochem. J. (2002) [Pubmed]
  23. Experimentally-induced irritant contact dermatitis. Determination of optimum irritant concentrations. Willis, C.M., Stephens, J.M., Wilkinson, J.D. Contact Derm. (1988) [Pubmed]
  24. Autoantibody-mediated atherosclerosis. Matsuura, E., Kobayashi, K., Koike, T., Shoenfeld, Y. Autoimmunity reviews. (2002) [Pubmed]
  25. 4-hydroxy-2-nonenal levels increase in the plasma of patients with adult respiratory distress syndrome as linoleic acid appears to fall. Quinlan, G.J., Evans, T.W., Gutteridge, J.M. Free Radic. Res. (1994) [Pubmed]
  26. Steric course of deuterium incorporation from [2-2H2]malonyl-CoA into fatty acids by fatty acid synthetases. Saito, K., Kawaguchi, A., Seyama, Y., Yamakawa, T., Okuda, S. J. Biochem. (1981) [Pubmed]
  27. Anti-beta 2-glycoprotein I autoantibodies and atherosclerosis. Matsuura, E., Kobayashi, K., Kasahara, J., Yasuda, T., Makino, H., Koike, T., Shoenfeld, Y. Int. Rev. Immunol. (2002) [Pubmed]
  28. Synthesis of [9-14C]nonanoic acid via 2-thienyl(14CH3)(cyano)cuprate and its oxidation by newborn piglet muscle strips. Tetrick, M.A., Crenshaw, T.D., Benevenga, N.J. Anal. Biochem. (1997) [Pubmed]
  29. Proteomic analysis of skin irritation reveals the induction of HSP27 by sodium lauryl sulphate in human skin. Boxman, I.L., Hensbergen, P.J., Van Der Schors, R.C., Bruynzeel, D.P., Tensen, C.P., Ponec, M. Br. J. Dermatol. (2002) [Pubmed]
  30. Clinical morphology of sodium lauryl sulfate (SLS) and nonanoic acid (NAA) irritant patch test reactions at 48 h and 96 h in 152 subjects. Reiche, L., Willis, C., Wilkinson, J., Shaw, S., de Lacharrière, O. Contact Derm. (1998) [Pubmed]
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