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Chemical Compound Review

delphinate     3-methylbutanoic acid

Synonyms: isovalerate, Isovalerianic, isopentanoate, isovalerianate, Delphinic acid, ...
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Disease relevance of METHYLBUTANOIC ACID


Psychiatry related information on METHYLBUTANOIC ACID

  • Isovaleric acid (iso5:0) is an unusual fatty acid that is important for echolocation and hearing in acoustic tissues of some odontocetes, but its functional significance in blubber is unknown [6].

High impact information on METHYLBUTANOIC ACID

  • For two unrelated ligands, androstenone and isovaleric acid, induction of olfactory sensitivity was odorant-specific and occurred only in inbred strains that initially had low sensitivity to the exposure odorant [7].
  • Isovaleric acidemia (IVA) is an inborn error of leucine metabolism, resulting in an accumulation of isovaleric acid in the body fluids [8].
  • Isovaleryl-PL was almost completely hydrolyzed to PL and isovaleric acid (IVA) in epithelial cells at a rate limited by its uptake [9].
  • A high intake of n-3 polyunsaturated fatty acids has been suggested as a factor in prolonged gestation in the population of the Faroe Islands. It is now suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor [10].
  • As a result, foot odor was found to be derived from isovaleric acid, which is produced when Staphylococcus epidermidis, a resident species of the normal cutaneous microbial flora, degrades leucine present in sweat [11].

Chemical compound and disease context of METHYLBUTANOIC ACID

  • The presence of appreciable amounts of succinic acid, more than 1 microM per ml, propionic and isovaleric acid, at concentrations not exceeding 3 microM per ml, was strong evidence for Bacteroides fragilis infections [12].

Biological context of METHYLBUTANOIC ACID

  • The batch experiments were consistent between the two systems and with the past literature: acetic and isovaleric acid were the most efficient substrates, and propionic acid was the least efficient of the 2-5 carbon VFAs (lack of acclimation was ruled out) [13].
  • A survey of the engineering and biochemical literature revealed that both acetic and isovaleric acid resulted in a negative reaction redox balance (i.e. it requires reducing equivalents such as NADH2) during their biotransformation to polyhydroxyalkanoates (PHAs) [13].
  • It was ascertained by measuring membrane fluidity using ESR that this assembly may be able to detect individually added chemical stimulants such as short-chain-bearing odorants (isovaleric acid, isovaleraldehyde, and isoamyl alcohol etc) at a concentration of 3 x 10(-4) parts to 1 part water [14].

Anatomical context of METHYLBUTANOIC ACID


Associations of METHYLBUTANOIC ACID with other chemical compounds

  • This study evaluated the effect of branched-chain volatile fatty acids (VFA; isobutyric acid, isovaleric acid), amino acids (valine, leucine), and dipeptides (valine-valine, leucine-leucine) on neutral detergent fiber (NDF) degradation by rumen microorganisms in vitro [20].
  • Four strains that produced a terminal VFA peak of isovaleric acid formed a new group designated 'ivoricus'. Reliable features for the identification of P. anaerobius were GLC (all GPAC that produced isocaproic acid were identified as P. anaerobius), enzyme profile and sensitivity to SPS [21].
  • Decreasing dietary CP reduced manure pH (P = 0.01), NH4 (P = 0.01), isovaleric acid (P = 0.06), phenol (P = 0.05), and 4-ethyl phenol (P = 0.02) concentrations [22].

Analytical, diagnostic and therapeutic context of METHYLBUTANOIC ACID


  1. The genetic basis for specific anosmia to isovaleric acid in the mouse. Griff, I.C., Reed, R.R. Cell (1995) [Pubmed]
  2. Metabolism of [1-(14)C] and [2-(14)C] leucine in cultured skin fibroblasts from patients with isovaleric acidemia. Characterization of metabolic defects. Tanaka, K., Mandell, R., Shih, V.E. J. Clin. Invest. (1976) [Pubmed]
  3. The tracing of the pathway of mevalonate's metabolism to other than sterols. Brady, P.S., Scofield, R.F., Schumann, W.C., Ohgaku, S., Kumaran, K., Margolis, J.M., Landau, B.R. J. Biol. Chem. (1982) [Pubmed]
  4. A novel biosynthetic pathway providing precursors for fatty acid biosynthesis and secondary metabolite formation in myxobacteria. Mahmud, T., Bode, H.B., Silakowski, B., Kroppenstedt, R.M., Xu, M., Nordhoff, S., Höfle, G., Müller, R. J. Biol. Chem. (2002) [Pubmed]
  5. Gas-liquid chromatography of positive blood cultures for rapid presumptive diagnosis of anaerobic bacteremia. Edson, R.S., Rosenblatt, J.E., Washington, J.A., Stewart, J.B. J. Clin. Microbiol. (1982) [Pubmed]
  6. High concentrations of isovaleric acid in the fats of odontocetes: variation and patterns of accumulation in blubber vs. stability in the melon. Koopman, H.N., Iverson, S.J., Read, A.J. J. Comp. Physiol. B, Biochem. Syst. Environ. Physiol. (2003) [Pubmed]
  7. Induction of olfactory receptor sensitivity in mice. Wang, H.W., Wysocki, C.J., Gold, G.H. Science (1993) [Pubmed]
  8. Cerebellar hemorrhage complicating isovaleric acidemia: a case report. Fischer, A.Q., Challa, V.R., Burton, B.K., McLean, W.T. Neurology (1981) [Pubmed]
  9. First-pass hydrolysis of a propranolol ester derivative in rat small intestine. Masaki, K., Taketani, M., Imai, T. Drug Metab. Dispos. (2006) [Pubmed]
  10. Birthweights in the Faroe Islands: possible role of isovaleric acid. Ackman, R.G. J. Intern. Med. (1989) [Pubmed]
  11. Foot odor due to microbial metabolism and its control. Ara, K., Hama, M., Akiba, S., Koike, K., Okisaka, K., Hagura, T., Kamiya, T., Tomita, F. Can. J. Microbiol. (2006) [Pubmed]
  12. Direct quantitative determination of acidic end products in clinical specimens for presumptive diagnosis of anaerobic infections. Legakis, N.J., Xanthopoulou, K., Ioannidou, H., Papavassiliou, J. Ann. Microbiol. (Paris) (1982) [Pubmed]
  13. A biochemical hypothesis explaining the response of enhanced biological phosphorus removal biomass to organic substrates. Hood, C.R., Randall, A.A. Water Res. (2001) [Pubmed]
  14. A study of chemoreception based on membrane fluidity and circular dichroism of a membrane assembly model--role of protein penetrating into the lipid bilayer. Ishigami, Y., Gama, Y., Someno, K., Kaise, M., Ishizuka, Y., Ishii, F. Biochem. Int. (1989) [Pubmed]
  15. Evaluation of diet as a cause of gastric ulcers in horses. Nadeau, J.A., Andrews, F.M., Mathew, A.G., Argenzio, R.A., Blackford, J.T., Sohtell, M., Saxton, A.M. Am. J. Vet. Res. (2000) [Pubmed]
  16. A short-chain acyl-CoA: 1-alkyl-2-acyl-sn-glycerol acyltrasnferase from a microsomal fraction of the rabbit Harderian gland. Rock, C.O., Snyder, F. Biochim. Biophys. Acta (1975) [Pubmed]
  17. Brain lipids from the porpoise (Delphinus delphis). Phosphoglycerides rich in isovaleric acid and long-chain iso-acids. Varanasi, U., Malins, D.C. Biochim. Biophys. Acta (1975) [Pubmed]
  18. A mechanism of toxicity of isovaleric acid in rat liver mitochondria. Bergen, B.J., Stumpf, D.A., Haas, R., Parks, J.K., Eguren, L.A. Biochemical medicine. (1982) [Pubmed]
  19. Effect of deaerated water on serum biochemical values and on the cecum concentration of short-chain fatty acids in the rat. Koseki, M., Seki, H., Sato, T., Yamashita, M., Ida, H., Honda, K. Biosci. Biotechnol. Biochem. (1996) [Pubmed]
  20. Response of forage fiber degradation by ruminal microorganisms to branched-chain volatile fatty acids, amino acids, and dipeptides. Yang, C.M. J. Dairy Sci. (2002) [Pubmed]
  21. The laboratory identification of gram-positive anaerobic cocci. Murdoch, D.A., Mitchelmore, I.J. J. Med. Microbiol. (1991) [Pubmed]
  22. Manure composition of swine as affected by dietary protein and cellulose concentrations. Kerr, B.J., Ziemer, C.J., Trabue, S.L., Crouse, J.D., Parkin, T.B. J. Anim. Sci. (2006) [Pubmed]
  23. Comparison of the sensitivity of C57BL/6J and AKR/J mice to airborne molecules of isovaleric acid and amyl acetate. Pourtier, L., Sicard, G. Behav. Genet. (1990) [Pubmed]
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