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Chemical Compound Review

octylate     octanoate

Synonyms: Caprylate, ETHYLHEXANOATE, n-octoate, n-octylate, n-caprylate, ...
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Disease relevance of octanoic acid


High impact information on octanoic acid

  • The reaction rate for catalytic hydrolysis of p-nitrophenyl caprylate was small when the gel was swollen [6].
  • The Mexican shrub Cuphea hookeriana accumulates up to 75% caprylate (8:0) and caprate (10:0) in its seed oil [7].
  • The seed oil of Cuphea palustris has an unusual fatty-acyl composition, whereby the principal fatty-acyl groups, myristate (64%) and caprylate (20%), differ by more than two methylenes [8].
  • Enzymatic assays of filtered culture supernatants revealed butyrate esterase and caprylate esterase lipase activity for 11 of 12 strains, as well as acid phosphatase, naphthol-AS-BI-phosphohydrolase, and beta-glucosidase activities in some strains [9].
  • Study of metabolites in the perfusate suggested that significant glycolysis occurred when the pO2 was 150 mm Hg: it was stimulated by caprylate and inhibited by raising the pO2 to 650 mm Hg [10].

Chemical compound and disease context of octanoic acid


Biological context of octanoic acid


Anatomical context of octanoic acid

  • These actions of caprylate on membranes are considered one possible mechanism by which it promotes the absorption of water-soluble and poorly absorbed drugs [15].
  • AIMS: The aim of our study was to examine the absorption of insulin from the gastrointestinal (GI) tract, using a novel oral formulation-adding a delivery agent SNAC (sodium N-[8-(2-hydroxybenzoyl)amino] caprylate) in combination with insulin [16].
  • The presence of feces or feed also had a significant effect (P < 0.01) on the antibacterial property of caprylate; the presence of feces decreased the antibacterial effect, whereas addition of feed enhanced the effect [4].
  • In this study we investigated the mechanism of insulin absorption across caco-2 cell monolayers with one of these drug delivery agents, N-[8-(2-hydroxybenzoyl)amino] caprylate (SNAC) [17].
  • The effects of sodium salts of medium-chain fatty acids, caprylate and caprate, on the penetration of a hydrophilic compound and a macromolecular compound across rabbit corneas in vitro were examined [18].

Associations of octanoic acid with other chemical compounds

  • METHODS: BSP-loaded nanospheres were prepared by an emulsion solvent diffusion method in oil (caprylate and caprate triglyceride) [19].
  • Addition of saturated fatty acids (butyrate, caprylate, laurate, palmitate and stearate) in a medium at 1 mmol/l, despite effects on the basal release, significantly reduced the ACTH release induced by CRH (1 nmol/l) stimulation [20].
  • Based on ideal solution theory, phase diagrams are calculated for binary compositions of cholesteryl esters and compared to experimental data from pairwise combinations in a saturated acyl chain series from caprylate to arachidate, which encompasses three crystal packing motifs in the solid state [21].
  • Tris(isopropylphenyl/phenyl) phosphates and triethylene glycol dicaprate/caprylate mixtures of typical industrial compositions have been analyzed by fast atom bombardment (FAB) mass spectrometry, FAB collisional activation (CA) mass-analyzed ion kinetic energy spectroscopy and FAB/electron impact (EI) CA B/E linked scans [22].

Gene context of octanoic acid

  • In the presence of caprylate (1 mmol/l), CRH (1 nmol/l)-stimulated increase in cellular calcium ion concentration was diminished [20].
  • A rapid colorimetric assay for the extracellular lipase of Pseudomonas fluorescens B52 using beta-naphthyl caprylate [23].
  • Selected topics in immunohematology: II. Albumin autoagglutination phenomenon (antibodies to albumin-bound caprylate) [24].

Analytical, diagnostic and therapeutic context of octanoic acid


  1. The apeE gene of Salmonella typhimurium encodes an outer membrane esterase not present in Escherichia coli. Carinato, M.E., Collin-Osdoby, P., Yang, X., Knox, T.M., Conlin, C.A., Miller, C.G. J. Bacteriol. (1998) [Pubmed]
  2. Paralogous gene analysis reveals a highly enantioselective 1,2-O-isopropylideneglycerol caprylate esterase of Bacillus subtilis. Dröge, M.J., Bos, R., Quax, W.J. Eur. J. Biochem. (2001) [Pubmed]
  3. Determination of the extracellular lipases of Pseudomonas fluorescens spp. in skim milk with the beta-naphthyl caprylate assay. McKellar, R.C., Cholette, H. J. Dairy Res. (1986) [Pubmed]
  4. Inactivation of escherichia coli O157:H7 in cattle drinking water by sodium caprylate. Amalaradjou, M.A., Annamalai, T., Marek, P., Rezamand, P., Schreiber, D., Hoagland, T., Venkitanarayanan, K. J. Food Prot. (2006) [Pubmed]
  5. Inactivation of West Nile virus, vaccinia virus and viral surrogates for relevant and emergent viral pathogens in plasma-derived products. Remington, K.M., Trejo, S.R., Buczynski, G., Li, H., Osheroff, W.P., Brown, J.P., Renfrow, H., Reynolds, R., Pifat, D.Y. Vox Sang. (2004) [Pubmed]
  6. Gel catalysts that switch on and off. Wang, G., Kuroda, K., Enoki, T., Grosberg, A., Masamune, S., Oya, T., Takeoka, Y., Tanaka, T. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  7. Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana. Dehesh, K., Jones, A., Knutzon, D.S., Voelker, T.A. Plant J. (1996) [Pubmed]
  8. Two novel thioesterases are key determinants of the bimodal distribution of acyl chain length of Cuphea palustris seed oil. Dehesh, K., Edwards, P., Hayes, T., Cranmer, A.M., Fillatti, J. Plant Physiol. (1996) [Pubmed]
  9. Extracellular proteins of Cryptococcus neoformans and host antibody response. Chen, L.C., Pirofski, L.A., Casadevall, A. Infect. Immun. (1997) [Pubmed]
  10. Metabolism of normal and ischemically injured rabbit kidneys during perfusion for 48 hours at 10 C. Pegg, D.E., Wusteman, M.C., Foreman, J. Transplantation (1981) [Pubmed]
  11. Investigation of fatty acid esters to replace isopropyl myristate in the sterility test for ophthalmic ointments. Cardoso, V.M., Solano, A.G., Prado, M.A., Nunan, E.d.e. .A. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  12. Platelet reactivity ex vivo and in vivo after acute and chronic treatment with sodium caprylate. Tangen, O., Wallenbeck, I.A., Bergqvist, D. Scand. J. Clin. Lab. Invest. (1975) [Pubmed]
  13. Overexpression and characterization of a lipase from Bacillus subtilis. Ma, J., Zhang, Z., Wang, B., Kong, X., Wang, Y., Cao, S., Feng, Y. Protein Expr. Purif. (2006) [Pubmed]
  14. Site-specific immunosuppression using a new formulation of topical cyclosporine A with polyethylene glycol-8 glyceryl caprylate/caprate. Tran, H.S., Malli, D., Chrzanowski, F.A., Puc, M.M., Matthews, M.S., Hewitt, C.W. J. Surg. Res. (1999) [Pubmed]
  15. Fluorescence study of the membrane-perturbing action of sodium caprylate as related to promotion of drug absorption. Kajii, H., Horie, T., Hayashi, M., Awazu, S. Journal of pharmaceutical sciences. (1988) [Pubmed]
  16. A novel per-oral insulin formulation: proof of concept study in non-diabetic subjects. Kidron, M., Dinh, S., Menachem, Y., Abbas, R., Variano, B., Goldberg, M., Arbit, E., Bar-On, H. Diabet. Med. (2004) [Pubmed]
  17. Oral delivery of insulin with the eligen technology: mechanistic studies. Malkov, D., Angelo, R., Wang, H.Z., Flanders, E., Tang, H., Gomez-Orellana, I. Current drug delivery. (2005) [Pubmed]
  18. Effect of medium-chain fatty acid salts on penetration of a hydrophilic compound and a macromolecular compound across rabbit corneas. Morimoto, K., Nakamura, T., Morisaka, K. Archives internationales de pharmacodynamie et de thérapie. (1989) [Pubmed]
  19. Prolonged anti-inflammatory action of DL-lactide/glycolide copolymer nanospheres containing betamethasone sodium phosphate for an intra-articular delivery system in antigen-induced arthritic rabbit. Horisawa, E., Hirota, T., Kawazoe, S., Yamada, J., Yamamoto, H., Takeuchi, H., Kawashima, Y. Pharm. Res. (2002) [Pubmed]
  20. Saturated fatty acids suppress adrenocorticotropic hormone (ACTH) release from rat anterior pituitary cells in vitro. Katoh, K., Asari, M., Ishiwata, H., Sasaki, Y., Obara, Y. Comp. Biochem. Physiol., Part A Mol. Integr. Physiol. (2004) [Pubmed]
  21. Co-solubility of saturated cholesteryl esters: a comparison of calculated and experimental binary phase diagrams. Dorset, D.L. Biochim. Biophys. Acta (1988) [Pubmed]
  22. Gas chromatography/electron impact mass spectrometry, fast atom bombardment mass spectrometry, mass-analyzed ion kinetic energy spectroscopy and B/E linked scan analysis of triaryl phosphates and triethylene glycol fatty acid esters. Feistner, G.J., Pascoe, N., Faull, K.F., Tomer, K.B. Biomed. Environ. Mass Spectrom. (1990) [Pubmed]
  23. A rapid colorimetric assay for the extracellular lipase of Pseudomonas fluorescens B52 using beta-naphthyl caprylate. McKellar, R.C. J. Dairy Res. (1986) [Pubmed]
  24. Selected topics in immunohematology: II. Albumin autoagglutination phenomenon (antibodies to albumin-bound caprylate). Hossaini, A.A. Progress in clinical pathology. (1978) [Pubmed]
  25. Properties of a new intravenous immunoglobulin (IGIV-C, 10%) produced by virus inactivation with caprylate and column chromatography. Lebing, W., Remington, K.M., Schreiner, C., Paul, H.I. Vox Sang. (2003) [Pubmed]
  26. Thermal stability of human albumin measured by differential scanning calorimetry. I. Effects of caprylate and N-acetyltryptophanate. Shrake, A., Finlayson, J.S., Ross, P.D. Vox Sang. (1984) [Pubmed]
  27. Inactivation of lipid-enveloped viruses in proteins by caprylate. Lundblad, J.L., Seng, R.L. Vox Sang. (1991) [Pubmed]
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