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Chemical Compound Review

CCHO     7-oxabicyclo[4.1.0]heptane

Synonyms: NSC-5218, AC-293, ACMC-1CIMB, CCRIS 1227, AG-C-85293, ...
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Disease relevance of Tetramethyleneoxirane

  • Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase [1].
  • The epoxide hydrolase (EH) from Corynebacterium sp. C12, which grows on cyclohexene oxide as sole carbon source, has been purified to homogeneity in two steps, involving anion exchange followed by hydrophobic-interaction chromatography [2].

High impact information on Tetramethyleneoxirane

  • Incubation of 17AAG with human hepatic microsomes and cyclohexene oxide, a known inhibitor of microsomal epoxide hydrolase, did not affect the production of metabolite 4 but decreased the production of metabolite 2 while increasing the production of metabolite 6 [3].
  • Cytotoxicity of teroxirone against continuous human tumor cell lines is abolished in the presence of 9000 X g rat liver supernatant preparations but partially restored when cyclohexene oxide is added to incubation mixtures [4].
  • The catalysis of the reaction of carbon dioxide with epoxides (cyclohexene oxide or propylene oxide) using the (salen)Cr(III)Cl complex as catalyst, where H(2)salen = N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexenediimine (1), to provide copolymer and cyclic carbonate has been investigated by in situ infrared spectroscopy [5].
  • When the epoxide hydrolase inhibitors, 1,1,1-trichloropropene-2,3-oxide or cyclohexene oxide were added to the incubations, binding increased 2.5- to 4-fold, suggesting epoxidation as a mechanism of adduct formation in vitro [6].
  • The coupling of carbon dioxide and mono-substituted terminal epoxides or cyclohexene oxide to form cyclic carbonates under a Ni complex catalyst system without using additional organic solvents was achieved in excellent selectivity and TOF [7].

Biological context of Tetramethyleneoxirane


Anatomical context of Tetramethyleneoxirane


Associations of Tetramethyleneoxirane with other chemical compounds


Gene context of Tetramethyleneoxirane

  • The amounts of monoepoxides formed as a balance between epoxidation and hydrolysis, was measured in incubations with and without the epoxide hydrolase inhibitor cyclohexene oxide [19].
  • With the exception of cyclohexene oxide, all the compounds were weak inhibitors of EH and glutathione S-transferase (GST) activities [20].
  • (R,R)-(salen-)CoX (X = Cl, Br, I, OAc, pentafluorobenzoate (OBzF(5))) catalysts are active for the copolymerization of cyclohexene oxide (CHO) and CO(2), yielding syndiotactic poly(cyclohexene carbonate) (PCHC), a previously unreported PCHC microstructure [21].

Analytical, diagnostic and therapeutic context of Tetramethyleneoxirane


  1. Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols. Chang, D., Wang, Z., Heringa, M.F., Wirthner, R., Witholt, B., Li, Z. Chem. Commun. (Camb.) (2003) [Pubmed]
  2. Characterisation of a catabolic epoxide hydrolase from a Corynebacterium sp. Misawa, E., Chan Kwo Chion, C.K., Archer, I.V., Woodland, M.P., Zhou, N.Y., Carter, S.F., Widdowson, D.A., Leak, D.J. Eur. J. Biochem. (1998) [Pubmed]
  3. Metabolism of 17-(allylamino)-17-demethoxygeldanamycin (NSC 330507) by murine and human hepatic preparations. Egorin, M.J., Rosen, D.M., Wolff, J.H., Callery, P.S., Musser, S.M., Eiseman, J.L. Cancer Res. (1998) [Pubmed]
  4. Pharmacological characterization of teroxirone, a triepoxide antitumor agent, in rats, rabbits, and humans. Ames, M.M., Kovach, J.S., Rubin, J. Cancer Res. (1984) [Pubmed]
  5. Comparative kinetic studies of the copolymerization of cyclohexene oxide and propylene oxide with carbon dioxide in the presence of chromium salen derivatives. In situ FTIR measurements of copolymer vs cyclic carbonate production. Darensbourg, D.J., Yarbrough, J.C., Ortiz, C., Fang, C.C. J. Am. Chem. Soc. (2003) [Pubmed]
  6. DNA adducts of the ubiquitous environmental contaminant cyclopenta[cd]pyrene. Beach, A.C., Gupta, R.C. Carcinogenesis (1994) [Pubmed]
  7. A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides. Li, F., Xia, C., Xu, L., Sun, W., Chen, G. Chem. Commun. (Camb.) (2003) [Pubmed]
  8. Generation and reactions of a selenoamide dianion. Murai, T., Aso, H., Kato, S. Org. Lett. (2002) [Pubmed]
  9. Absorption, disposition kinetics, and metabolic pathways of cyclohexene oxide in the male Fischer 344 rat and female B6C3F1 mouse. Sauer, J.M., Bao, J., Smith, R.L., McClure, T.D., Mayersohn, M., Pillai, U., Cunningham, M.L., Sipes, I.G. Drug Metab. Dispos. (1997) [Pubmed]
  10. Induction of sister chromatid exchanges by styrene and its presumed metabolite styrene oxide in the presence of rat liver homogenate. de Raat, W.K. Chem. Biol. Interact. (1978) [Pubmed]
  11. Simultaneous determination of cyclohexene oxide and its metabolites in rat plasma and urine by gas chromatography. Bao, J., Smith, R.L., Sauer, J.M., Pillai, U., Sipes, I.G. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]
  12. Disposition and metabolism of the angiogenic moderator O-(chloroacetyl-carbamoyl) fumagillol (TNP-470; AGM-1470) in human hepatocytes and tissue microsomes. Placidi, L., Cretton-Scott, E., de Sousa, G., Rahmani, R., Placidi, M., Sommadossi, J.P. Cancer Res. (1995) [Pubmed]
  13. Metabolism of aflatoxin B1 in cultured mouse hepatocytes: comparison with rat and effects of cyclohexene oxide and diethyl maleate. Decad, G.M., Dougherty, K.K., Hsieh, D.P., Byard, J.L. Toxicol. Appl. Pharmacol. (1979) [Pubmed]
  14. Protein-reactive metabolites of carbamazepine in mouse liver microsomes. Lillibridge, J.H., Amore, B.M., Slattery, J.T., Kalhorn, T.F., Nelson, S.D., Finnell, R.H., Bennett, G.D. Drug Metab. Dispos. (1996) [Pubmed]
  15. Alkylating properties and genetic activity of 4-vinylcyclohexene metabolites and structurally related epoxides. Turchi, G., Bonatti, S., Citti, L., Gervasi, P.G., Abbondandolo, A. Mutat. Res. (1981) [Pubmed]
  16. Identification of 2,3-epoxymethacrylic acid as an intermediate in the metabolism of dental materials in human liver microsomes. Seiss, M., Nitz, S., Kleinsasser, N., Buters, J.T., Behrendt, H., Hickel, R., Reichl, F.X. Dental materials : official publication of the Academy of Dental Materials (2007) [Pubmed]
  17. An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides. Xiao, Y., Jung, D., Gund, T., Malhotra, S.V. Journal of molecular modeling (Online) (2006) [Pubmed]
  18. Evaluation of the developmental toxicity of thalidomide using frog embryo teratogenesis assay-xenopus (FETAX): biotransformation and detoxification. Fort, D.J., Stover, E.L., Bantle, J.A., Finch, R.A. Teratog., Carcinog. Mutagen. (2000) [Pubmed]
  19. The biotransformation of isoprene and the two isoprene monoepoxides by human cytochrome P450 enzymes, compared to mouse and rat liver microsomes. Bogaards, J.J., Venekamp, J.C., van Bladeren, P.J. Chem. Biol. Interact. (1996) [Pubmed]
  20. 1,2-Epoxycycloalkanes: substrates and inhibitors of microsomal and cytosolic epoxide hydrolases in mouse liver. Magdalou, J., Hammock, B.D. Biochem. Pharmacol. (1988) [Pubmed]
  21. Copolymerization of cyclohexene oxide and carbon dioxide using (salen)Co(III) complexes: synthesis and characterization of syndiotactic poly(cyclohexene carbonate). Cohen, C.T., Thomas, C.M., Peretti, K.L., Lobkovsky, E.B., Coates, G.W. Dalton transactions (Cambridge, England : 2003) (2006) [Pubmed]
  22. Carbon dioxide/epoxide coupling reactions utilizing Lewis base adducts of zinc halides as catalysts. Cyclic carbonate versus polycarbonate production. Darensbourg, D.J., Lewis, S.J., Rodgers, J.L., Yarbrough, J.C. Inorganic chemistry. (2003) [Pubmed]
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