The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Capronic acid     hexanoic acid

Synonyms: hexylate, capronate, hexoate, pentylformate, n-hexoate, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Capronic acid


High impact information on Capronic acid

  • AgLDL release was decreased >90% by inhibitors of plasmin (epsilon-amino caproic acid and anti-plasminogen mAb), and also by inhibitors of urokinase plasminogen activator (plasminogen activator inhibitor-1 and anti-urokinase plasminogen activator mAb) [5].
  • On the interaction of the finger and the kringle-2 domain of tissue-type plasminogen activator with fibrin. Inhibition of kringle-2 binding to fibrin by epsilon-amino caproic acid [6].
  • A vasoactive intestinal polypeptide (VIP) analog, acylated on the amino-terminal histidine by hexanoic acid (C(6)-VIP), behaved as a VPAC(2) preferring agonist in binding and functional studies on human VIP receptors, and radioiodinated C(6)-VIP was a suitable ligand for binding studies on wild-type and chimeric receptors [7].
  • For example, compound 7b which has a hexanoic acid side chain inhibited AMPDA with a K(i) = 4.2 microM and ADA with a K(i) = 280 microM [8].
  • A competitive fluoroimmunoassay for the caproic acid conjugate of 2-phenyloxazolone as a model antigen was performed with the immunoliposomes [9].

Chemical compound and disease context of Capronic acid


Biological context of Capronic acid

  • We have also established that 1-hexanoic acid and 4-methylbenzoic acid do not interact significantly with kringle 4 (Ka less than 0.05 mM-1) [11].
  • On the other hand, conjugation with caproic acid slightly suppressed TG's hepatic first-pass metabolism, which suggests that chemically modified TGs with fatty acids would be more stable than the native TG in the systemic circulation after intestinal absorption [12].
  • Felbinac, which is a substrate, inhibited the activity of this medium chain acyl-CoA synthetase for hexanoic acid (IC50 = 25 microM) [13].
  • Effect of epsilon amino caproic acid, a fibrinolytic inhibitor, on implantation and fetal viability in the rat [14].
  • The hydrolysis of C30PHPC by human pancreatic phospholipase A2 was followed by monitoring the increase in the pyrene monomer fluorescence emission intensity occurring as a consequence of transfer of the reaction product, pyren-1-yl hexanoic acid into the aqueous phase [15].

Anatomical context of Capronic acid

  • Furthermore, by an in vitro modified Ussing chamber method, it was revealed that the permeability of insulin across both the duodenal and colonic mucous membranes was also improved by increasing the number of caproic acid molecules [16].
  • M-5 and M-6 were further biotransformed to a ketol derivative and C-C bond cleavage metabolite (hexanoic acid derivative), an in vivo end product, in the incubation with dog liver microsomes [17].
  • A protocol was developed for the analysis of volatile short chain fatty acids in microsamples of feces, short chain fatty acid (SCFA) extraction was from fecal samples using ethanol incorporating n-hexanoic acid as an internal standard [18].
  • The effect of caproic acid, handling technique and storage times on the fertility of fowl spermatozoa [19].
  • Trypsin-like esterases, hydrolyzing epsilon-amino caproic acid naphtol-AS-D.HBr (ACA), were found in the active form in both submandibular gland and pancreatic homogenates [20].

Associations of Capronic acid with other chemical compounds


Gene context of Capronic acid

  • The protease inhibitors, Epsilon Amino Caproic Acid (E.A.C.A.) and Aprotinin were found to significantly increase the inhibition produced by P.P.D. in the Leucocyte Migration Test (L.M.T.). Dose-response curves showed that the most effective concentrations were for E.A.C.A. 0.01 M and Aprotinin 100 I.U./ml [25].
  • The dipeptide coupled to the dextran matrix appears to be a preferred substrate for plasminogen binding compared to free lysine and epsilon-amino caproic acid [26].
  • Differential scanning calorimetry (DSC) is employed in a study of the effects of the p-nitrophenyl esters of the even numbered fatty acids from C6 (caproic acid) to C18 (stearic acid) on the main phase transition of multilamellar suspensions of dimyristoylphosphatidylcholine (DMPC) [27].
  • Proteolytic cleavage of the protein chains was observed during purification and storage in the absence of the protease inhibitor 6-amino caproic acid [28].
  • A series of renin inhibitors containing the dipeptide transition state mimics (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-cyclohexyl hexanoic acid (Cha-psi[CH(OH)CH2]Ala) and (2R,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-cyclohexyl hexanoic acid (Cha-psi[CH(OH)CH2]Val) were prepared [29].

Analytical, diagnostic and therapeutic context of Capronic acid

  • To understand the mechanism of affinity maturation, we examined the antigen-antibody interactions between 4-hydroxy-3-nitrophenylacetyl (NP) caproic acid and the Fab fragments of three anti-NP antibodies, N1G9, 3B44, and 3B62, by isothermal titration calorimetry [30].
  • This report describes a rapid method for the identification of C. difficile, using gas-liquid chromatography (GLC) for the demonstration of caproic acid, a product of the organisms fatty acid metabolism [2].
  • The lactic and/or caproic acid repeat units can be hydrolyzed under physiological conditions, leading to degradable networks that may be useful for tissue engineering applications [31].
  • The denatured protein in 6 M guanidine X HCl was reduced and carboxymethylated, dialyzed through 6 M urea/preservatives and to 1% ammonium acetate/0.05% EDTA/0.13% epsilon-amino caproic acid, pH 7.3 under N2 at 4 degrees C. The morphological studies were carried out by electron microscopy with negative staining and freeze fracture [32].
  • The addition of hexanoic acid to the perfusion solution (buffer c) abolished the effect of oxfenicine [33].


  1. Phagocytosis of the A band following Z line, and I band loss. Its significance in skeletal muscle breakdown. Cullen, M.J., Fulthorpe, J.J. J. Pathol. (1982) [Pubmed]
  2. Stool caproic acid for screening of Clostridium difficile. Madan, E., Slifkin, M. Am. J. Clin. Pathol. (1988) [Pubmed]
  3. Pathologic hyperfibrinolysis associated with amyloidosis: clinical response to epsilon amino caproic acid. Chang, J.C., Kane, K.K. Am. J. Clin. Pathol. (1984) [Pubmed]
  4. Medium-chain fatty acids decrease colonization and invasion through hilA suppression shortly after infection of chickens with Salmonella enterica serovar Enteritidis. Van Immerseel, F., De Buck, J., Boyen, F., Bohez, L., Pasmans, F., Volf, J., Sevcik, M., Rychlik, I., Haesebrouck, F., Ducatelle, R. Appl. Environ. Microbiol. (2004) [Pubmed]
  5. Plasmin-mediated macrophage reversal of low density lipoprotein aggregation. Zhang, W.Y., Ishii, I., Kruth, H.S. J. Biol. Chem. (2000) [Pubmed]
  6. On the interaction of the finger and the kringle-2 domain of tissue-type plasminogen activator with fibrin. Inhibition of kringle-2 binding to fibrin by epsilon-amino caproic acid. van Zonneveld, A.J., Veerman, H., Pannekoek, H. J. Biol. Chem. (1986) [Pubmed]
  7. Different vasoactive intestinal polypeptide receptor domains are involved in the selective recognition of two VPAC(2)-selective ligands. Juarranz, M.G., Van Rampelbergh, J., Gourlet, P., De Neef, P., Cnudde, J., Robberecht, P., Waelbroeck, M. Mol. Pharmacol. (1999) [Pubmed]
  8. AMP deaminase inhibitors. 2. Initial discovery of a non-nucleotide transition-state inhibitor series. Bookser, B.C., Kasibhatla, S.R., Appleman, J.R., Erion, M.D. J. Med. Chem. (2000) [Pubmed]
  9. A fluoroimmunoassay based on immunoliposomes containing genetically engineered lipid-tagged antibody. Kobatake, E., Sasakura, H., Haruyama, T., Laukkanen, M.L., Keinänen, K., Aizawa, M. Anal. Chem. (1997) [Pubmed]
  10. Norleucine-tyrosine broth for rapid identification of Clostridium difficile by gas-liquid chromatography. Nunez-Montiel, O.L., Thompson, F.S., Dowell, V.R. J. Clin. Microbiol. (1983) [Pubmed]
  11. Ligand specificity of human plasminogen kringle 4. Rejante, M.R., Byeon, I.J., Llinás, M. Biochemistry (1991) [Pubmed]
  12. Enhanced permeability of tetragastrin across the rat intestinal membrane and its reduced degradation by acylation with various fatty acids. Yodoya, E., Uemura, K., Tenma, T., Fujita, T., Murakami, M., Yamamoto, A., Muranishi, S. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  13. Inhibitory effect of quinolone antimicrobial and nonsteroidal anti-inflammatory drugs on a medium chain acyl-CoA synthetase. Kasuya, F., Hiasa, M., Kawai, Y., Igarashi, K., Fukui, M. Biochem. Pharmacol. (2001) [Pubmed]
  14. Effect of epsilon amino caproic acid, a fibrinolytic inhibitor, on implantation and fetal viability in the rat. Dubin, N.H., Cummings, D.B., Blake, D.A., King, T.M. Biol. Reprod. (1980) [Pubmed]
  15. Hydrolysis of 1-triacontanoyl-2-(pyren-1-yl)hexanoyl-sn-glycero-3-phosphocholine by human pancreatic phospholipase A2. Thurén, T., Virtanen, J.A., Vainio, P., Kinnunen, P.K. Chem. Phys. Lipids (1983) [Pubmed]
  16. Absorption characteristics of chemically modified-insulin derivatives with various fatty acids in the small and large intestine. Asada, H., Douen, T., Waki, M., Adachi, S., Fujita, T., Yamamoto, A., Muranishi, S. Journal of pharmaceutical sciences. (1995) [Pubmed]
  17. Oxidative cleavage of the octyl side chain of 1-(3,4-dichlorobenzyl)-5-octylbiguanide (OPB-2045) in rat and dog liver preparations. Umehara, K., Kudo, S., Hirao, Y., Morita, S., Uchida, M., Odomi, M., Miyamoto, G. Drug Metab. Dispos. (2000) [Pubmed]
  18. Gas-liquid chromatographic analysis of volatile short chain fatty acids in fecal samples as pentafluorobenzyl esters. McGrath, L.T., Weir, C.D., Maynard, S., Rowlands, B.J. Anal. Biochem. (1992) [Pubmed]
  19. The effect of caproic acid, handling technique and storage times on the fertility of fowl spermatozoa. Macpherson, J.W., Fiser, P.S., Reinhart, B.S. Poult. Sci. (1977) [Pubmed]
  20. Localization of kallikrein and its relation to other trypsin-like esterases in the rat pancreas. A comparison with the submandibular gland. Orstavik, T.B., Glenner, G.G. Acta Physiol. Scand. (1978) [Pubmed]
  21. Role of EETs in regulation of endothelial permeability in rat lung. Alvarez, D.F., Gjerde, E.A., Townsley, M.I. Am. J. Physiol. Lung Cell Mol. Physiol. (2004) [Pubmed]
  22. Growth-dependent changes in endothelial factors regulating arteriolar tone. Samora, J.B., Frisbee, J.C., Boegehold, M.A. Am. J. Physiol. Heart Circ. Physiol. (2007) [Pubmed]
  23. Quantification of azo-coupled lysine in azo proteins by amino acid analysis. Pielak, G.J., Gurusiddaiah, S., Legg, J.I. Anal. Biochem. (1986) [Pubmed]
  24. Development of new lipophilic derivatives of tetragastrin: physicochemical characteristics and intestinal absorption of acyl-tetragastrin derivatives in rats. Tenma, T., Yodoya, E., Tashima, S., Fujita, T., Murakami, M., Yamamoto, A., Muranishi, S. Pharm. Res. (1993) [Pubmed]
  25. The effect of protease inhibitors on leucocyte migration inhibition to tuberculin extract (P.P.D.). Burden, A.C., Stacey, R.L., Wood, R.F., Bell, P.R. Immunology (1978) [Pubmed]
  26. Selective plasminogen binding: cysteinyl-lysine-dextran protein interactions. Warkentin, P.H. Biomaterials (1998) [Pubmed]
  27. The effects of the p-nitrophenyl esters of the even-numbered fatty acids from caproic (C6) to stearic (C18) on the main phase transition of dimyristoylphosphatidylcholine. Bae, S.J., Sturtevant, J.M. Chem. Phys. Lipids (1993) [Pubmed]
  28. A reinvestigation on the quaternary structure of ascorbate oxidase from Cucurbita pepo medullosa. Avigliano, L., Vecchini, P., Sirianni, P., Marcozzi, G., Marchesini, A., Mondovi, B. Mol. Cell. Biochem. (1983) [Pubmed]
  29. Synthesis and biological activity of potent, low molecular weight renin inhibitors. Sueiras-Diaz, J., Jones, D.M., Szelke, M., Deinum, J., Svensson, L., Westerlund, C., Sohtell, M. J. Pept. Res. (1997) [Pubmed]
  30. The affinity maturation of anti-4-hydroxy-3-nitrophenylacetyl mouse monoclonal antibody. A calorimetric study of the antigen-antibody interaction. Torigoe, H., Nakayama, T., Imazato, M., Shimada, I., Arata, Y., Sarai, A. J. Biol. Chem. (1995) [Pubmed]
  31. Photoinitiated crosslinked degradable copolymer networks for tissue engineering applications. Davis, K.A., Burdick, J.A., Anseth, K.S. Biomaterials (2003) [Pubmed]
  32. Apolipoprotein B is a globular protein--morphological studies by electron microscopy. Lee, D.M., Stiers, D.L., Mok, T. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  33. Role of the fuel utilized by tissues on coronary vessel response to physical stimuli in isolated rat hearts. Pagliaro, P., Gattullo, D. Physiological research / Academia Scientiarum Bohemoslovaca. (2004) [Pubmed]
WikiGenes - Universities