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Chemical Compound Review

ISOBUTANE     2-methylpropane

Synonyms: iso-butane, Isobutane (NF), AGN-PC-0052G3, HSDB 608, AG-B-71593, ...
 
 
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Disease relevance of isobutane

 

High impact information on isobutane

  • The measured activation energy for isobutane H/D exchange is 57 kJ/mol [4].
  • The hydroxylation step involves a concerted but nonsynchronous transfer of a hydrogen atom from this newly formed, bound, water molecule to the ferryl oxygen with a concomitant rebound of the incipient *OH radical to the carbon radical of isobutane to produce the C-O bond of the final product, tert-butyl alcohol [5].
  • In situ 13C MAS NMR and complementary ex situ GC-MS data provided evidence for a monomolecular mechanism of the 13C-label scrambling, whereas both isobutane and propane are formed through intermolecular pathways [6].
  • Advantages of ammonia ionization over the previously studied isobutane ionization include a 130-270% enhancement in the sensitivity of base peak monitoring, and direct determination of molecular weight from the base peak (M + NH4+) in the mass spectrum of any of the derivatives [7].
  • Negative chemical ionization mass spectrometry with a mixture of isobutane, methylene chloride, and oxygen as the reagent gas has been used to explore contamination of environmental substrates with xenobiotic chemicals [8].
 

Chemical compound and disease context of isobutane

 

Biological context of isobutane

  • Eight adult volunteers of both sexes were exposed to isobutane in a controlled-environment chamber for the purpose of monitoring their physiological responses to a series of gas concentrations ranging from 250 to 1,000 ppm [9].
  • The alkylation of butene with isobutane on WO(3)/ZrO(2) was carried out in a fixed-bed reactor [10].
  • Reaction kinetics data were collected for isobutane conversion over a series of ultra stable Y (USY) zeolite catalysts with and without rare earth cations and subjected to various extents of dealumination by steaming [11].
 

Anatomical context of isobutane

  • Ultrasonographic appearance of exogenous isobutane gas in the mammary glands of dairy cows [12].
  • OBJECTIVE: To determine whether exogenous isobutane gas infused into the udders of dairy cattle could be detected ultrasonographically, and if so, what effects volume of gas infused and infusion pressure had on how long after infusion exogenous isobutane gas could be detected [12].
 

Associations of isobutane with other chemical compounds

 

Gene context of isobutane

  • This bond energy is the strongest tertiary C-H bond to be measured, is much larger than the corresponding bond in isobutane (96.5 +/- 0.4 kcal/mol), and is more typical of an alkene or aromatic compound [18].
  • Their heptafluoropropionic (PFP) derivatives are ionized under electron impact and isobutane-chemical ionization [19].
  • Structural elucidation has been carried out by isobutane-chemical ionization mass spectrometry of the fatty acyl biosynthetic precursor-derived methyl ester [20].
  • For this reason, the authors have adapted gas chromatography/negative ion chemical ionization mass spectrometry (GC/NICI-MS) (developed by Ramesha and Pickett in 1985) by employing an SPB-1 column and isobutane as the reagent gas [21].
  • Urine was enzymatically hydrolyzed, cleaned up on a C18 micro-column and the metabolites were identified by GC-MS using electron impact (70 eV) and chemical ionization with ammonia or isobutane as the reagent gas [22].
 

Analytical, diagnostic and therapeutic context of isobutane

  • Isobutane was used as both gas chromatography (GC) carrier gas and chemical ionization (CI) reagent gas [23].
  • Broadband attenuation measurements are described for two different types of microbubble suspension (albumin encapsulated octofluropropane and copolymer encapsulated isobutane) to ascertain whether or not multiple scattering may be observed experimentally [24].
  • CONCLUSIONS AND CLINICAL RELEVANCE: Results suggest that exogenous isobutane gas infused into the mammary glands to enhance the appearance of the udder of show dairy cattle can be readily detected by ultrasonography [12].
  • In prospect, isobutane chemical ionization mass spectrometry seems to be a useful technique for peptide sequence determination, and may have advantages in some cases [25].

References

  1. Sudden death after isobutane sniffing: a report of two forensic cases. Pfeiffer, H., Al Khaddam, M., Brinkmann, B., Köhler, H., Beike, J. Int. J. Legal Med. (2006) [Pubmed]
  2. Triamcinolone acetonide spray (reformulated) in the treatment of topical steroid-responsive dermatoses. Goldner, R. International journal of dermatology. (1981) [Pubmed]
  3. Ventricular fibrillation following inhalation of Glade Air Freshener. LoVecchio, F., Fulton, S.E. European journal of emergency medicine : official journal of the European Society for Emergency Medicine. (2001) [Pubmed]
  4. Alkane C-H bond activation in zeolites: evidence for direct protium exchange. Truitt, M.J., Toporek, S.S., Rovira-Truitt, R., White, J.L. J. Am. Chem. Soc. (2006) [Pubmed]
  5. The "somersault" mechanism for the p-450 hydroxylation of hydrocarbons. The intervention of transient inverted metastable hydroperoxides. Bach, R.D., Dmitrenko, O. J. Am. Chem. Soc. (2006) [Pubmed]
  6. Mechanism studies of the conversion of 13C-labeled n-butane on zeolite H-ZSM-5 by using 13C magic angle spinning NMR spectroscopy and GC-MS analysis. Luzgin, M.V., Stepanov, A.G., Arzumanov, S.S., Rogov, V.A., Parmon, V.N., Wang, W., Hunger, M., Freude, D. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  7. Ammonia gas: an improved reagent for chemical ionization mass spectrometry of bile acid methyl ester acetates. DeMark, B.R., Klein, P.D. J. Lipid Res. (1981) [Pubmed]
  8. Negative chemical ionization studied of human and food chain contamination with xenobiotic chemicals. Dougherty, R.C., Whitaker, M.J., Smith, L.M., Stalling, D.L., Kuehl, D.W. Environ. Health Perspect. (1980) [Pubmed]
  9. Acute and repetitive human exposure to isobutane. Stewart, R.D., Herrmann, A.A., Baretta, E.D., Forster, H.V., Sikora, J.J., Newton, P.E., Soto, R.J. Scandinavian journal of work, environment & health. (1977) [Pubmed]
  10. Controllable synthesis, characterization and catalytic properties of WO(3)/ZrO(2) mixed oxides nanoparticles. Sun, W., Xu, L., Chu, Y., Shi, W. Journal of colloid and interface science. (2003) [Pubmed]
  11. Role of rare earth cations in Y zeolite for hydrocarbon cracking. Sanchez-Castillo, M.A., Madon, R.J., Dumesic, J.A. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
  12. Ultrasonographic appearance of exogenous isobutane gas in the mammary glands of dairy cows. Trostle, S.S., O'Brien, R.T., Britt, J., Waller, K.R. J. Am. Vet. Med. Assoc. (1999) [Pubmed]
  13. Neopentane as a possible replacement for isobutane in chemical ionization mass spectrometry. Allan, A.R., Roboz, J. Rapid Commun. Mass Spectrom. (1988) [Pubmed]
  14. Simple and sensitive quantitation method for mevalonic acid in plasma using gas chromatography/mass spectrometry. Ishihama, Y., Mano, N., Oda, Y., Hiyoshi, H., Ikuta, H., Yoshida, Y. Rapid Commun. Mass Spectrom. (1994) [Pubmed]
  15. Comparison of electron and chemical ionization mass spectrometry of sialic acids. Reuter, G., Schauer, R. Anal. Biochem. (1986) [Pubmed]
  16. Formation of 6-dimethylcarbamyloxy-dGuo, 6-dimethylamino-dGuo and 4-dimethylamino-dThd following in vitro reaction of dimethylcarbamyl chloride with calf thymus DNA and 6-diethylcarbamyloxy-dGuo following in vitro reaction of diethylcarbamyl chloride with calf thymus DNA. Segal, A., Solomon, J.J., Maté, U., Van Duuren, B.L. Chem. Biol. Interact. (1982) [Pubmed]
  17. Isolation and identification of terpenoid sex pheromone components from extracts of hemolymph of males of the Caribbean fruit fly. Teal, P.E., Meredith, J.A., Gomez-Simuta, Y. Arch. Insect Biochem. Physiol. (1999) [Pubmed]
  18. Formation of a 1-bicyclo[1.1.1]pentyl anion and an experimental determination of the acidity and C-H bond dissociation energy of 3-tert-butylbicyclo[1.1.1]pentane. Reed, D.R., Kass, S.R., Mondanaro, K.R., Dailey, W.P. J. Am. Chem. Soc. (2002) [Pubmed]
  19. The components of the venom of a spider Scodra griseipes. 2. Structural information on biogenic amines using tandem mass spectrometry. Lange, C., Paris, C., Celerier, M.L. Rapid Commun. Mass Spectrom. (1992) [Pubmed]
  20. Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland. Navarro, I., Mas, E., Fabriàs, G., Camps, F. Bioorg. Med. Chem. (1997) [Pubmed]
  21. Quantitative analysis of platelet activating factor treated with pentafluorobenzoyl chloride using gas chromatography/negative ion chemical ionization mass spectrometry. Shindo, K., Hashimoto, Y. Drugs under experimental and clinical research. (1991) [Pubmed]
  22. Gas chromatographic-mass spectrometric identification of metabolites from alpha-pinene in human urine after occupational exposure to sawing fumes. Eriksson, K., Levin, J.O. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  23. A method for the determination of amitriptyline and its metabolites nortriptyline, 10-hydroxyamitriptyline, and 10-hydroxynortriptyline in human plasma using stable isotope dilution and gas chromatography-chemical ionization mass spectrometry (GC-CIMS). Garland, W.A., Muccino, R.R., Min, B.H., Cupano, J., Fann, W.E. Clin. Pharmacol. Ther. (1979) [Pubmed]
  24. Investigating the significance of multiple scattering in ultrasound contrast agent particle populations. Stride, E., Saffari, N. IEEE transactions on ultrasonics, ferroelectrics, and frequency control. (2005) [Pubmed]
  25. Peptide sequencing: the utility of chemical ionization mass spectrometry. Mudgett, M., Bowen, D.V., Kindt, T.J. Biomed. Mass Spectrom. (1977) [Pubmed]
 
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