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Chemical Compound Review

caproate     hexanoate

Synonyms: hexylate, Hexanoate, capronate, hexoate, butylacetate, ...
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Disease relevance of Capronic acid

  • The cloned fragments could not only complement PHA-negative mutants of Alcaligenes eutrophus and Pseudomonas putida, but also confer the ability to synthesize P(3HB-co-3HHx) from octanoate or hexanoate on the mutants' hosts [1].
  • The recombinant esterase that was overexpressed and purified from E. coli was active above 30 degrees C up to 95 degrees C and had a high thermal stability [2].
  • The Clostridium bryantii-Methanospirillum hungatei syntrophic coculture, grown on caproate, was adapted to grow on crotonate [3].
  • We have previously reported that the spirostenol derivative (22R, 25R)-20alpha-spirost-5-en-3beta-yl hexanoate (SP-233) protects neuronal cells against Abeta(1-42) toxicity by binding to and inactivating the peptide [4].
  • We hypothesized that treatment with 17-OHP caproate is more effective in prolonging pregnancy depending on the gestational age of the earliest previous preterm birth (20-27.9, 28-33.9 vs 34-36.9 weeks) [5].

High impact information on Capronic acid


Chemical compound and disease context of Capronic acid


Biological context of Capronic acid

  • Differences between retinyl butyrate and retinyl caproate hydrolysis suggested the possible presence of two short-chain esterase activities associated with both rat and human BBMs, in addition to the long-chain activity [15].
  • During the simulation, a methyl hexanoate entered the active-site groove [16].
  • Transfection analyses indicate that inhibition of ACCalpha transcription by cAMP or hexanoate is mediated by ACCalpha sequences between -101 and -71 bp [17].
  • 2-Ketoisocaproate and 2-ketocaproate (2-oxo-, hexanoate) provoked changes in B cell electrical behavior characterized by an initial depolarization of the membrane potential, followed by rapid spike activity, which appeared either in a bursting pattern or as continuous activity [18].
  • Infusion of hexanoate increased oxygen consumption, while stepwise changes in the perfusate Ca2+ concentration in the range 0.5-2.5 mM caused the mechanical work output and oxygen consumption to change in parallel [19].

Anatomical context of Capronic acid

  • Transacylation as a chain-termination mechanism in fatty acid synthesis by mammalian fatty acid synthetase. Synthesis of butyrate and hexanoate by lactating cow mammary gland fatty acid synthetase [20].
  • Brush border membrane from animals who had undergone common duct ligation 48 h prior to tissue collection showed little ability to hydrolyze retinyl caproate but retained 70% of retinyl palmitate hydrolytic activity, compared to sham-operated controls [21].
  • In contrast, ketone body production from hexanoate, which is activated in the mitochondria, was not affected by ethylhexanol [22].
  • 4. In murine N9 microglial cell line, instead, sodium butyrate and other SCFAs (propionate, valerate and caproate) enhanced the LPS-induced inflammatory response [23].
  • The effect of TFC-612, methyl-6-[(1R,2S,3R)-hydroxy-2-](1E,3S,5R)-3- hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl)thio] hexanoate, on intimal thickening of carotid artery 14 days after endothelium denudation with a balloon catheter was examined in rats [24].

Associations of Capronic acid with other chemical compounds


Gene context of Capronic acid


Analytical, diagnostic and therapeutic context of Capronic acid


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  2. New thermophilic and thermostable esterase with sequence similarity to the hormone-sensitive lipase family, cloned from a metagenomic library. Rhee, J.K., Ahn, D.G., Kim, Y.G., Oh, J.W. Appl. Environ. Microbiol. (2005) [Pubmed]
  3. Assignment of Clostridium bryantii to Syntrophospora bryantii gen. nov., comb. nov. on the basis of a 16S rRNA sequence analysis of its crotonate-grown pure culture. Zhao, H.X., Yang, D.C., Woese, C.R., Bryant, M.P. Int. J. Syst. Bacteriol. (1990) [Pubmed]
  4. The spirostenol (22R, 25R)-20alpha-spirost-5-en-3beta-yl hexanoate blocks mitochondrial uptake of Abeta in neuronal cells and prevents Abeta-induced impairment of mitochondrial function. Tillement, L., Lecanu, L., Yao, W., Greeson, J., Papadopoulos, V. Steroids (2006) [Pubmed]
  5. Progesterone for prevention of recurrent preterm birth: impact of gestational age at previous delivery. Spong, C.Y., Meis, P.J., Thom, E.A., Sibai, B., Dombrowski, M.P., Moawad, A.H., Hauth, J.C., Iams, J.D., Varner, M.W., Caritis, S.N., O'Sullivan, M.J., Miodovnik, M., Leveno, K.J., Conway, D., Wapner, R.J., Carpenter, M., Mercer, B., Ramin, S.M., Thorp, J.M., Peaceman, A.M., Gabbe, S. Am. J. Obstet. Gynecol. (2005) [Pubmed]
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  8. Hexanoate and octanoate inhibit transcription of the malic enzyme and fatty acid synthase genes in chick embryo hepatocytes in culture. Roncero, C., Goodridge, A.G. J. Biol. Chem. (1992) [Pubmed]
  9. Quantification of carbon fluxes through the tricarboxylic acid cycle in early germinating lettuce embryos. Salon, C., Raymond, P., Pradet, A. J. Biol. Chem. (1988) [Pubmed]
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  11. Eubacterium pyruvativorans sp. nov., a novel non-saccharolytic anaerobe from the rumen that ferments pyruvate and amino acids, forms caproate and utilizes acetate and propionate. Wallace, R.J., McKain, N., McEwan, N.R., Miyagawa, E., Chaudhary, L.C., King, T.P., Walker, N.D., Apajalahti, J.H., Newbold, C.J. Int. J. Syst. Evol. Microbiol. (2003) [Pubmed]
  12. Prevention of premature labor by 17 alpha-hydroxyprogesterone caproate. Yemini, M., Borenstein, R., Dreazen, E., Apelman, Z., Mogilner, B.M., Kessler, I., Lancet, M. Am. J. Obstet. Gynecol. (1985) [Pubmed]
  13. Syntrophus aciditrophicus sp. nov., a new anaerobic bacterium that degrades fatty acids and benzoate in syntrophic association with hydrogen-using microorganisms. Jackson, B.E., Bhupathiraju, V.K., Tanner, R.S., Woese, C.R., McInerney, M.J. Arch. Microbiol. (1999) [Pubmed]
  14. Hormone mediated changes in monoamine stores and regulation of enzymes of biosynthesis and metabolism in the rat adrenal gland. Influence of progesterone, estradiol, ACTH and testosterone administration. Bukhari, A.R., Guessab, A., Nicol, M.L. Steroids (1981) [Pubmed]
  15. Retinyl ester hydrolytic activity associated with human intestinal brush border membranes. Rigtrup, K.M., McEwen, L.R., Said, H.M., Ong, D.E. Am. J. Clin. Nutr. (1994) [Pubmed]
  16. Dynamics of proteins in different solvent systems: analysis of essential motion in lipases. Peters, G.H., van Aalten, D.M., Edholm, O., Toxvaerd, S., Bywater, R. Biophys. J. (1996) [Pubmed]
  17. SREBP-1 integrates the actions of thyroid hormone, insulin, cAMP, and medium-chain fatty acids on ACCalpha transcription in hepatocytes. Zhang, Y., Yin, L., Hillgartner, F.B. J. Lipid Res. (2003) [Pubmed]
  18. Similarities in the stimulus-secretion coupling mechanisms of glucose- and 2-keto acid-induced insulin release. Hutton, J.C., Sener, A., Herchuelz, A., Atwater, I., Kawazu, S., Boschero, A.C., Somers, G., Devis, G., Malaisse, W.J. Endocrinology (1980) [Pubmed]
  19. Respiratory control in heart muscle during fatty acid oxidation. Energy state or substrate-level regulation by Ca2+? Vuorinen, K.H., Ala-Rämi, A., Yan, Y., Ingman, P., Hassinen, I.E. J. Mol. Cell. Cardiol. (1995) [Pubmed]
  20. Transacylation as a chain-termination mechanism in fatty acid synthesis by mammalian fatty acid synthetase. Synthesis of butyrate and hexanoate by lactating cow mammary gland fatty acid synthetase. Hansen, J.K., Knudsen, J. Biochem. J. (1980) [Pubmed]
  21. A retinyl ester hydrolase activity intrinsic to the brush border membrane of rat small intestine. Rigtrup, K.M., Ong, D.E. Biochemistry (1992) [Pubmed]
  22. Interactions between plasticizers and fatty acid metabolism in the perfused rat liver and in vivo. Inhibition of ketogenesis by 2-ethylhexanol. Badr, M.Z., Handler, J.A., Whittaker, M., Kauffman, F.C., Thurman, R.G. Biochem. Pharmacol. (1990) [Pubmed]
  23. Regulation of microglial inflammatory response by sodium butyrate and short-chain fatty acids. Huuskonen, J., Suuronen, T., Nuutinen, T., Kyrylenko, S., Salminen, A. Br. J. Pharmacol. (2004) [Pubmed]
  24. Effect of TFC-612, a 7-thia prostaglandin E1 derivative, on intimal thickening after endothelial injury with balloon catheter in rats. Motoyama, Y., Seki, J., Katoh, Y., Nishio, M., Yoshida, K. Atherosclerosis (1994) [Pubmed]
  25. Beta-Ketoacyl-acyl carrier protein synthetase. Characterization of the acyl-enzyme intermediate. D'Agnolo, G., Rosenfeld, I.S., Vagelos, P.R. J. Biol. Chem. (1975) [Pubmed]
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  29. Interaction of hydrophobic anions with the rat skeletal muscle chloride channel ClC-1: effects on permeation and gating. Rychkov, G.Y., Pusch, M., Roberts, M.L., Bretag, A.H. J. Physiol. (Lond.) (2001) [Pubmed]
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  33. Self-cloning yeast strains containing novel FAS2 mutations produce a higher amount of ethyl caproate in Japanese sake. Aritomi, K., Hirosawa, I., Hoshida, H., Shiigi, M., Nishizawa, Y., Kashiwagi, S., Akada, R. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
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