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Chemical Compound Review:

Isobuten 2-methylprop-1-ene

Synonyms: Isobutene, ISOBUTYLENE, Methylpropene, gamma-Butylene, AGN-PC-00JDFK, ...

Fukuda, H. et al., Cornet, M. et al., Cornet, M. et al., Fukuda, H. et al., Zhu, G. et al., et al.

Bonrath, Schiefer,

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Disease relevance of isobutylene

Metabolism and toxicity of 2-methylpropene (isobutene)--a review [1].
Mutagenicity of 2-methylpropene (isobutene) and its epoxide in a modified Salmonella assay for volatile compounds [2].

High impact information on isobutylene

We investigated the adsorption states of 2-methylpropene and propene on Si(100)c(4x2) using low-temperature scanning tunneling microscopy [3].
For example, the activity of JML-1 in the production of gasoline by alkylation of 1-butene with isobutene remained at 95% or higher after 20 h of reaction and was over 90% after being regenerated five times [4].
The bromonium ion derived from 1 is less stable by 6.3 kcal mol-1 than that from isobutene [5].
The involvement of rat liver cytochrome P450 2E1 in the activation of 2-methylpropene to its epoxide 2-methyl-1,2-epoxypropane has been established [6].
The biotransformation of 2-methylpropene, a gaseous alkene widely used in industry, was investigated in vitro in liver tissue of rats, mice, and humans [6].

Chemical compound and disease context of isobutylene

The mutagenic properties of 2-methylpropene (MP) and 2-methyl-1,2- epoxypropane (MEP) were investigated in the Salmonella assay [2].

Biological context of isobutylene

This result indicates that formation of isobutene might be initiated by abstraction of hydrogen from the beta carbon of isovalerate and might be followed by decarboxylation [7].
Metabolism of isobutene (2-methylpropene) in rats (Sprague Dawley) and mice (B6C3F1) follows kinetics according to Michaelis-Menten [8].

Anatomical context of isobutylene

Comparative mutagenicity of 2-methylpropene (isobutene), its epoxide 2-methyl-1,2-epoxypropane and propylene oxide in the in vitro micronucleus test using human lymphocytes [9].

Associations of isobutylene with other chemical compounds

The formation of isobutene can be explained by rearrangement to prenal, oxidation to 3,3-dimethylacrylic acid and then decarboxylation [10].
A reconstituted system that consisted of purified P450rm and cytochrome P450 reductase catalyzed the 4-hydroxylation of benzoate in addition to the formation of isobutene; the turnover rate was approximately 40 nmol/min/nmol P450rm [11].
In this work, the biotransformation of 2-methylpropene (MP) has been studied, using total liver homogenates of mice, supplemented with a NADPH-generating system [12].
Protonated isobutene in zeolites: tert-butyl cation or alkoxide [13]?

Gene context of isobutylene

An isobutene-forming activity was reconstituted with cytochrome P450rm and cytochrome P450 reductase purified from Rhodotorula minuta [7].
The main differences were located in the presence of isobutene isomers in Ring Type A, which were absent in Ring Type B [14].

References

Metabolism and toxicity of 2-methylpropene (isobutene)--a review. Cornet, M., Rogiers, V. Crit. Rev. Toxicol. (1997) [Pubmed]
Mutagenicity of 2-methylpropene (isobutene) and its epoxide in a modified Salmonella assay for volatile compounds. Cornet, M., Castelain, P., Vercruysse, A., Laib, R., Kirsch-Volders, M., Rogiers, V. Mutat. Res. (1992) [Pubmed]
Regioselective Cycloaddition Reaction of Alkene Molecules with the Asymmetric Dimer on Si(100)c(4x2). Oguchi, K., Nagao, M., Umeyama, H., Katayama, T., Yamashita, Y., Mukai, K., Yoshinobu, J., Akagi, K., Tsuneyuki, S. J. Am. Chem. Soc. (2007) [Pubmed]
Highly effective sulfated zirconia nanocatalysts grown out of colloidal silica at high temperature. Zhu, G., Wang, C., Zhang, Y., Guo, N., Zhao, Y., Wang, R., Qiu, S., Wei, Y., Baughman, R.H. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
Reactivities of methylenetriangulanes and spirocyclopropanated bicyclopropylidenes toward bromine. Relative stabilities of spirocyclopropanated versus methyl-substituted bromonium ions. Kozhushkov, S., Späth, T., Fiebig, T., Galland, B., Ruasse, M.F., Xavier, P., Apeloig, Y., de Meijere, A. J. Org. Chem. (2002) [Pubmed]
Species-dependent differences in biotransformation pathways of 2-methylpropene (isobutene). Cornet, M., Callaerts, A., Jorritsma, U., Bolt, H., Vercruysse, A., Rogiers, V. Chem. Res. Toxicol. (1995) [Pubmed]
Reconstitution of the isobutene-forming reaction catalyzed by cytochrome P450 and P450 reductase from Rhodotorula minuta: decarboxylation with the formation of isobutene. Fukuda, H., Fujii, T., Sukita, E., Tazaki, M., Nagahama, S., Ogawa, T. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
Investigation of species differences in isobutene (2-methylpropene) metabolism between mice and rats. Csanády, G.A., Freise, D., Denk, B., Filser, J.G., Cornet, M., Rogiers, V., Laib, R.J. Arch. Toxicol. (1991) [Pubmed]
Comparative mutagenicity of 2-methylpropene (isobutene), its epoxide 2-methyl-1,2-epoxypropane and propylene oxide in the in vitro micronucleus test using human lymphocytes. Jorritsma, U., Cornet, M., Van Hummelen, P., Bolt, H.M., Vercruysse, A., Kirsch-Volders, M., Rogiers, V. Mutagenesis (1995) [Pubmed]
Bis(acetylacetonato) dioxomolybdenum(VI) catalysed rearrangement of methylbutynol in the presence of ultrasound. Bonrath, W., Schiefer, G. Ultrasonics sonochemistry. (1999) [Pubmed]
Cytochrome P450rm from Rhodotorula minuta catalyzes 4-hydroxylation of benzoate. Fukuda, H., Nakamura, K., Sukita, E., Ogawa, T., Fujii, T. J. Biochem. (1996) [Pubmed]
In vitro biotransformation of 2-methylpropene (isobutene): epoxide formation in mice liver. Cornet, M., Sonck, W., Callaerts, A., Csanády, G., Vercruysse, A., Laib, R.J., Rogiers, V. Arch. Toxicol. (1991) [Pubmed]
Protonated isobutene in zeolites: tert-butyl cation or alkoxide? Tuma, C., Sauer, J. Angew. Chem. Int. Ed. Engl. (2005) [Pubmed]
Combined GC and sniffing port analysis of volatile compounds in rubber rings mounted on beer bottles. Linssen, J.P., Rijnen, L., Legger-Huiysman, A., Roozen, J.P. Food additives and contaminants. (1998) [Pubmed]

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