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Chemical Compound Review

Acinetten     hexanedioic acid

Synonyms: Adipinate, adipate, Acifloctin, Adipinsaure, Adilactetten, ...
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Disease relevance of hexanedioic acid


High impact information on hexanedioic acid


Chemical compound and disease context of hexanedioic acid


Biological context of hexanedioic acid

  • Several putative open reading frames (ORFs) that were expected to encode enzymes catalyzing the conversion of cyclohexanol to adipic acid were identified [3].
  • Fusion analyses showed that pcaI and pcaJ constitute an operon which requires beta-ketoadipate or its nonmetabolizable analog, adipate, as well as the pcaR regulatory gene for induction [16].
  • A solid-phase extraction (SPE) method was developed for the simultaneous extraction of dicarboxylic acids and diols formed during hydrolysis of poly(butylene succinate), PBS, and poly(butylene adipate), PBA [17].
  • After three to five residence times, adipate degradation and ad-7-ADCA production disappeared, and this allowed determination of the biomass yield coefficient on adipate [18].
  • The metabolism and pharmacokinetics of [2H10]di-2-(ethylhexyl) adipate (DEHA) labelled on the ethyl side-chains was determined in six male volunteers [19].

Anatomical context of hexanedioic acid

  • Identification and quantification of alpha-amino adipic acid in bovine dentine phosphoprotein [20].
  • Adipic acid (AA) was found to be the main urinary metabolite; it was also detected in the digestive tract, blood and liver [21].
  • A normal degradation rate of DL-alpha-amino [1-14C] adipic acid in fibroblasts of the patient, as measured by 14CO2 production, did not indicate a primary enzyme defect in the alpha-aminoadipic acid transamination or decarboxylation steps [22].
  • Concentrations of benzylpenicillin and spiramycin adipate were determined in bovine plasma and milk and in lymph draining the udder tissue after IM or IV administration [23].
  • In Exp. 1, nursery pigs (n = 14) were fed (for a period of 7 d) either a standard nursery diet or the same diet supplemented with 1% adipic acid to assess effects on urinary pH (collected on d 5 or 6) and in vitro ammonia emission from the collected urine samples that were mixed with control feces [24].

Associations of hexanedioic acid with other chemical compounds

  • Baseline concentrations of glycerol, FFA, and adipate were 44 +/- 15, 449 +/- 152, and 8 - 8 mumol/liter in N and 39 +/- 14, 473 +/- 44, and 41 +/- 14 (P less than 0.01) in IDDM [10].
  • Solid-phase microextraction (SPME) coupled to gas chromatography-mass spectrometry (GC-MS) has been applied to determine six phthalate esters and one adipate ester in water [25].
  • The aqueous solubilities of albuterol free base, sulfate, adipate, and stearate were 15.7, 250, 353, and 0.6 mg . mL-1, respectively, at room temperature [26].
  • By comparing the biodegradation degree of the scaffolds added with amino acids and their model compounds, i.e. adipic acid and hexane diamine, the key factor influencing the biological stability was further investigated [27].
  • Development of a solid-phase extraction method for simultaneous extraction of adipic acid, succinic acid and 1,4-butanediol formed during hydrolysis of poly(butylene adipate) and poly(butylene succinate) [17].

Gene context of hexanedioic acid

  • Our results suggest that the uni-directional activity of LKR plays an important role in regulating the catabolic function of the alpha-amino adipic acid pathway in plants [28].
  • Two patients with mild variants of the same disorder (MAD:M) presented with neurologic abnormalities, acidotic coma, and/or poor growth; they primarily excreted ethylmalonate and variable amounts of adipate [29].
  • In the cases of glutaric and adipic acid, the strength of the intramolecular hydrogen bond were estimated to be around 28-29 kJ/mol, without any vibrational energy correction [30].
  • Isolation of alpha-amino adipic acid from mature dermal collagen and elastin. Evidence for an oxidative pathway in the maturation of collagen and elastin [31].
  • Zeta potential measurements show that the assembly is significantly less positively charged in the presence of deprotonated adipic acid than when adipic acid is fully protonated [32].

Analytical, diagnostic and therapeutic context of hexanedioic acid


  1. Acute transitory cerebellar dysfunction associated with piperazine adipate. Berger, J.R., Globus, M., Melamed, E. Arch. Neurol. (1979) [Pubmed]
  2. The metabolism of benzoate by Moraxella species through anaerobic nitrate respiration. Evidence for a reductive pathway. Williams, R.J., Evans, W.C. Biochem. J. (1975) [Pubmed]
  3. Genetic analysis of a gene cluster for cyclohexanol oxidation in Acinetobacter sp. Strain SE19 by in vitro transposition. Cheng, Q., Thomas, S.M., Kostichka, K., Valentine, J.R., Nagarajan, V. J. Bacteriol. (2000) [Pubmed]
  4. Effects of DL-alpha-amino adipic acid on Müller cells in frog and chicken retinae in vivo: relation to ERG b wave, ganglion cell discharge and tectal evoked potentials. Bonaventure, N., Roussel, G., Wioland, N. Neurosci. Lett. (1981) [Pubmed]
  5. Biodegradation of poly(anhydride-esters) into non-steroidal anti-inflammatory drugs and their effect on Pseudomonas aeruginosa biofilms in vitro and on the foreign-body response in vivo. Bryers, J.D., Jarvis, R.A., Lebo, J., Prudencio, A., Kyriakides, T.R., Uhrich, K. Biomaterials (2006) [Pubmed]
  6. Short-chain acyl-coenzyme A dehydrogenase deficiency. Clinical and biochemical studies in two patients. Amendt, B.A., Greene, C., Sweetman, L., Cloherty, J., Shih, V., Moon, A., Teel, L., Rhead, W.J. J. Clin. Invest. (1987) [Pubmed]
  7. A prokaryotic gene cluster involved in synthesis of lysine through the amino adipate pathway: a key to the evolution of amino acid biosynthesis. Nishida, H., Nishiyama, M., Kobashi, N., Kosuge, T., Hoshino, T., Yamane, H. Genome Res. (1999) [Pubmed]
  8. Gender differences in medium-chain dicarboxylic aciduria in alcoholic men and women. Ma, X., Baraona, E., Goozner, B.G., Lieber, C.S. Am. J. Med. (1999) [Pubmed]
  9. Specificity of basolateral organic anion exchanger in proximal tubule for cellular and extracellular solutes. Sullivan, L.P., Grantham, J.J. J. Am. Soc. Nephrol. (1992) [Pubmed]
  10. Type I diabetes is characterized by insulin resistance not only with regard to glucose, but also to lipid and amino acid metabolism. Trevisan, R., Nosadini, R., Avogaro, A., Lippe, G., Duner, E., Fioretto, P., Deana, R., Tessari, P., Tiengo, A., Velussi, M. J. Clin. Endocrinol. Metab. (1986) [Pubmed]
  11. Observations on cell kinetics and viability of a human melanoma cell line exposed to dicarboxylic acids in tissue culture. Breathnach, A.S., Robins, E.J., Bhasin, Y., Ethridge, L., Nazzaro-Porro, M., Passi, S., Picardo, M. Histol. Histopathol. (1986) [Pubmed]
  12. Assimilation of citric acid and adipic acid by the blue-green alga Anabaena variabilis. Butler, M., Capindale, J.B. Can. J. Microbiol. (1975) [Pubmed]
  13. 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]
  14. Final report on the safety assessment of Stearamide DIBA-Stearate. Lanigan, R.S. International journal of toxicology. (2001) [Pubmed]
  15. Influence of the adipate and dissolved oxygen concentrations on the beta-lactam production during continuous cultivations of a Penicillium chrysogenum strain expressing the expandase gene from Streptomyces clavuligerus. Robin, J., Bonneau, S., Schipper, D., Noorman, H., Nielsen, J. Metab. Eng. (2003) [Pubmed]
  16. Regulation of the pcaIJ genes for aromatic acid degradation in Pseudomonas putida. Parales, R.E., Harwood, C.S. J. Bacteriol. (1993) [Pubmed]
  17. Development of a solid-phase extraction method for simultaneous extraction of adipic acid, succinic acid and 1,4-butanediol formed during hydrolysis of poly(butylene adipate) and poly(butylene succinate). Lindström, A., Albertsson, A.C., Hakkarainen, M. Journal of chromatography. A. (2004) [Pubmed]
  18. Continuous cultivations of a Penicillium chrysogenum strain expressing the expandase gene from Streptomyces clavuligerus: Growth yields and morphological characterization. Robin, J., Lettier, G., McIntyre, M., Noorman, H., Nielsen, J. Biotechnol. Bioeng. (2003) [Pubmed]
  19. Metabolism and pharmacokinetics of deuterium-labelled di-2-(ethylhexyl) adipate (DEHA) in humans. Loftus, N.J., Laird, W.J., Steel, G.T., Wilks, M.F., Woollen, B.H. Food Chem. Toxicol. (1993) [Pubmed]
  20. Identification and quantification of alpha-amino adipic acid in bovine dentine phosphoprotein. Hiraoka, B.Y., Fukasawa, K., Fukasawa, K.M., Harada, M. J. Biochem. (1980) [Pubmed]
  21. Elimination, distribution and metabolism of di-(2-ethylhexyl)adipate (DEHA) in rats. Takahashi, T., Tanaka, A., Yamaha, T. Toxicology (1981) [Pubmed]
  22. alpha-Aminoadipic aciduria and persistence of fetal haemoglobin in an oligophrenic child. Manders, A.J., von Oostrom, C.G., Trijbels, J.M., Rutten, F.J., Kleijer, W.J. Eur. J. Pediatr. (1981) [Pubmed]
  23. Concentrations of penicillin, streptomycin, and spiramycin in bovine udder tissue liquids. Franklin, A., Horn af Rantzien, M., Obel, N., Ostensson, K., Aström, G. Am. J. Vet. Res. (1986) [Pubmed]
  24. Dietary adipic acid reduces ammonia emission from swine excreta. van Kempen, T.A. J. Anim. Sci. (2001) [Pubmed]
  25. Comparison of different fibers for the solid-phase microextraction of phthalate esters from water. Peñalver, A., Pocurull, E., Borrull, F., Marcé, R.M. Journal of chromatography. A. (2001) [Pubmed]
  26. Preparation, characterization, and dissolution kinetics of two novel albuterol salts. Jashnani, R.N., Dalby, R.N., Byron, P.R. Journal of pharmaceutical sciences. (1993) [Pubmed]
  27. Enhanced biological stability of collagen porous scaffolds by using amino acids as novel cross-linking bridges. Ma, L., Gao, C., Mao, Z., Zhou, J., Shen, J. Biomaterials (2004) [Pubmed]
  28. The catabolic function of the alpha-aminoadipic acid pathway in plants is associated with unidirectional activity of lysine-oxoglutarate reductase, but not saccharopine dehydrogenase. Zhu, X., Tang, G., Galili, G. Biochem. J. (2000) [Pubmed]
  29. Clinical and biochemical variation and family studies in the multiple acyl-CoA dehydrogenation disorders. Rhead, W.J., Wolff, J.A., Lipson, M., Falace, P., Desai, N., Fritchman, K., Moon, A., Sweetman, L. Pediatr. Res. (1987) [Pubmed]
  30. Conformations, energies, and intramolecular hydrogen bonds in dicarboxylic acids: implications for the design of synthetic dicarboxylic acid receptors. Nguyen, T.H., Hibbs, D.E., Howard, S.T. Journal of computational chemistry. (2005) [Pubmed]
  31. Isolation of alpha-amino adipic acid from mature dermal collagen and elastin. Evidence for an oxidative pathway in the maturation of collagen and elastin. Bailey, A.J., Ranta, M.H., Nicholls, A.C., Partridge, S.M., Elsden, D.F. Biochem. Biophys. Res. Commun. (1977) [Pubmed]
  32. pH-triggered assembly of gold nanorods. Orendorff, C.J., Hankins, P.L., Murphy, C.J. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  33. Structure of the adipate complex [Na2(C6H9O4)2(C6H10O4)].2H2O from neutron diffraction at 220 and 295 K. Gao, Q., Clancy, L., Weber, H.P., Craven, B.M., McMullan, R.K. Acta Crystallogr., B (1991) [Pubmed]
  34. Fabrication of microspheres using blends of poly(ethylene adipate) and poly(ethylene adipate)/poly(hydroxybutyrate-hydroxyvalerate) with poly(caprolactone): incorporation and release of bovine serum albumin. Atkins, T.W. Journal of biomaterials science. Polymer edition. (1997) [Pubmed]
  35. A kinetic method for quantification of aspartate aminotransferase isoenzymes. Gracia, R., Busquets, M., Gil, M., Cortés, A., Bozal, J. J. Biochem. Biophys. Methods (1987) [Pubmed]
  36. Organic acids or urine in multiple sclerosis. Steen, G., Ransnäs, L. Acta neurologica Scandinavica. (1983) [Pubmed]
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