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Chemical Compound Review

Epoxypropane     2-methyloxirane

Synonyms: Methyloxirane, propylenoxide, Propyleneoxide, CCRIS 540, Propene oxide, ...
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Disease relevance of Methyloxacyclopropane


Psychiatry related information on Methyloxacyclopropane

  • We estimated the risk associated with the consumption of raw almonds and the risk reduction associated with almonds treated with a theoretical 5-log reduction process or treated with propylene oxide using a standard commercial process [3].

High impact information on Methyloxacyclopropane


Chemical compound and disease context of Methyloxacyclopropane


Biological context of Methyloxacyclopropane


Anatomical context of Methyloxacyclopropane


Associations of Methyloxacyclopropane with other chemical compounds


Gene context of Methyloxacyclopropane

  • Using a wide range of block copolymers, differing in hydrophilic-lipophilic balance (HLB), this study shows that lipophilic Pluronics with intermediate length of propylene oxide block (from 30 to 60 units) and HLB <20 are the most effective at inhibiting Pgp efflux in BBMECs [25].
  • Since depletion of nasal non-protein sulfhydryls (NPSH) may be important in the toxicity of this vapor and may serve as a biomarker for delivery of propylene oxide to nasal tissues, measurements of respiratory and olfactory NPSH content after propylene oxide exposure were also made [26].
  • Mutagenic activity of ethylene oxide and propylene oxide under XPG proficient and deficient conditions in relation to N-7-(2-hydroxyalkyl)guanine levels in Drosophila [27].
  • Propylene oxide (CAS No. 75-56-9) was tested for mutagenic activity following vapor exposure using 3 in vivo test systems [28].
  • The backbone of the stars is a statistical copolymer of ethylene oxide and propylene oxide in the ratio 80:20 (Star PEG) [29].

Analytical, diagnostic and therapeutic context of Methyloxacyclopropane

  • Core electron transitions as a probe for molecular chirality: natural circular dichroism at the carbon K-edge of methyloxirane [30].
  • Intraperitoneal injections of propylene oxide at 2 x 300 mg/kg induced increased numbers of micronucleated erythrocytes in mice, but lower doses given by this route had no such effect [31].
  • The mutants were screened for altered stereoselectivity in the propene/epoxypropane reaction by a whole-cell assay, solvent extraction, and chiral gas chromatography analysis protocol that is suitable for scale up to several thousand mutants and that is estimated to detect differences in e.e. of as little as 5% [16].
  • Fixed and dehydrated cell culture layers were cut into small pieces and separated from the plastic dish by adding propylene oxide [32].
  • The HPLC method was developed to purify the hydroxylase component, and the purified protein has a specific activity of 541 nmol propene oxide x mg(-1) protein x min(-1), which is two times the specific activity of the protein purified by the two-step LC procedure [33].


  1. Nasal cavity neoplasia in F344/N rats and (C57BL/6 x C3H)F1 mice inhaling propylene oxide for up to two years. Renne, R.A., Giddens, W.E., Boorman, G.A., Kovatch, R., Haseman, J.E., Clarke, W.J. J. Natl. Cancer Inst. (1986) [Pubmed]
  2. Purification and characterization of two components of epoxypropane isomerase/carboxylase from Xanthobacter Py2. Chion, C.K., Leak, D.J. Biochem. J. (1996) [Pubmed]
  3. Monte Carlo simulations assessing the risk of salmonellosis from consumption of almonds. Danyluk, M.D., Harris, L.J., Schaffner, D.W. J. Food Prot. (2006) [Pubmed]
  4. 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]
  5. Structural basis for stereoselectivity in the (R)- and (S)-hydroxypropylthioethanesulfonate dehydrogenases. Krishnakumar, A.M., Nocek, B.P., Clark, D.D., Ensign, S.A., Peters, J.W. Biochemistry (2006) [Pubmed]
  6. Quantitation of DNA and hemoglobin adducts and apurinic/apyrimidinic sites in tissues of F344 rats exposed to propylene oxide by inhalation. Ríos-Blanco, M.N., Faller, T.H., Nakamura, J., Kessler, W., Kreuzer, P.E., Ranasinghe, A., Filser, J.G., Swenberg, J.A. Carcinogenesis (2000) [Pubmed]
  7. 32P-postlabelling of propylene oxide 1- and N(6)-substituted adenine and 3-substituted cytosine/uracil: formation and persistence in vitro and in vivo. Plna, K., Nilsson, R., Koskinen, M., Segerbäck, D. Carcinogenesis (1999) [Pubmed]
  8. Two short-chain dehydrogenases confer stereoselectivity for enantiomers of epoxypropane in the multiprotein epoxide carboxylating systems of Xanthobacter strain Py2 and Nocardia corallina B276. Allen, J.R., Ensign, S.A. Biochemistry (1999) [Pubmed]
  9. Carbon dioxide fixation in the metabolism of propylene and propylene oxide by Xanthobacter strain Py2. Small, F.J., Ensign, S.A. J. Bacteriol. (1995) [Pubmed]
  10. Characterization of 2-bromoethanesulfonate as a selective inhibitor of the coenzyme m-dependent pathway and enzymes of bacterial aliphatic epoxide metabolism. Boyd, J.M., Ellsworth, A., Ensign, S.A. J. Bacteriol. (2006) [Pubmed]
  11. Carcinogenic and toxicologic effects of inhaled ethylene oxide and propylene oxide in F344 rats. Lynch, D.W., Lewis, T.R., Moorman, W.J., Burg, J.R., Groth, D.H., Khan, A., Ackerman, L.J., Cockrell, B.Y. Toxicol. Appl. Pharmacol. (1984) [Pubmed]
  12. Propylene oxide mutagenesis at template cytosine residues. Snow, E.T., Singh, J., Koenig, K.L., Solomon, J.J. Environ. Mol. Mutagen. (1994) [Pubmed]
  13. Correspondence re: Czene et al., Analysis of DNA and hemoglobin adducts and sister chromatid exchanges in a human population occupationally exposed to propylene oxide: a pilot study. Cancer Epidemiol. Biomark. Prev., 11: 315-318, 2002. Albertini, R.J. Cancer Epidemiol. Biomarkers Prev. (2003) [Pubmed]
  14. Catalytic asymmetric addition of carbon dioxide to propylene oxide with unprecedented enantioselectivity. Berkessel, A., Brandenburg, M. Org. Lett. (2006) [Pubmed]
  15. DNA adducts of propylene oxide and acrylonitrile epoxide: hydrolytic deamination of 3-alkyl-dCyd to 3-alkyl-dUrd. Solomon, J.J., Segal, A. Environ. Health Perspect. (1989) [Pubmed]
  16. Protocol for mutagenesis of alkene monooxygenase and screening for modified enantiocomposition of the epoxypropane product. Perry, A., Smith, T.J. Journal of biomolecular screening : the official journal of the Society for Biomolecular Screening. (2006) [Pubmed]
  17. Production of high-quality particulate methane monooxygenase in high yields from Methylococcus capsulatus (bath) with a hollow-fiber membrane bioreactor. Yu, S.S., Chen, K.H., Tseng, M.Y., Wang, Y.S., Tseng, C.F., Chen, Y.J., Huang, D.S., Chan, S.I. J. Bacteriol. (2003) [Pubmed]
  18. Interaction of tumor and normal blood cells with ethylene oxide and propylene oxide block copolymers. Melik-Nubarov, N.S., Pomaz, O.O., Dorodnych TYu, n.u.l.l., Badun, G.A., Ksenofontov, A.L., Schemchukova, O.B., Arzhakov, S.A. FEBS Lett. (1999) [Pubmed]
  19. Morphometric study of cardiac muscle: the problem of tissue shrinkage. Gerdes, A.M., Kriseman, J., Bishop, S.P. Lab. Invest. (1982) [Pubmed]
  20. Rejoining of DNA strand breaks induced by propylene oxide and epichlorohydrin in human diploid fibroblasts. Chovanec, M., Näslund, M., Spivak, I., Dusinská, M., Cedervall, B., Kolman, A. Environ. Mol. Mutagen. (1998) [Pubmed]
  21. Identification and characterization of epoxide carboxylase activity in cell extracts of Nocardia corallina B276. Allen, J.R., Ensign, S.A. J. Bacteriol. (1998) [Pubmed]
  22. Ranking the potential carcinogenic hazards to workers from exposures to chemicals that are tumorigenic in rodents. Gold, L.S., Backman, G.M., Hooper, N.K., Peto, R. Environ. Health Perspect. (1987) [Pubmed]
  23. A DFT investigation of the addition reaction of monomeric lithium enolate derived from propiophenone to propene oxide: examination of the possible transition structures. Pomelli, C.S., Bianucci, A.M., Crotti, P., Favero, L. J. Org. Chem. (2004) [Pubmed]
  24. Acetonitrile as a substitute for ethanol/propylene oxide in tissue processing for transmission electron microscopy: comparison of fine structure and lipid solubility in mouse liver, kidney, and intestine. Edwards, H.H., Yeh, Y.Y., Tarnowski, B.I., Schonbaum, G.R. Microsc. Res. Tech. (1992) [Pubmed]
  25. Optimal structure requirements for pluronic block copolymers in modifying P-glycoprotein drug efflux transporter activity in bovine brain microvessel endothelial cells. Batrakova, E.V., Li, S., Alakhov, V.Y., Miller, D.W., Kabanov, A.V. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  26. Uptake of inspired propylene oxide in the upper respiratory tract of the f344 rat. Morris, J.B., Banton, M.I., Pottenger, L.H. Toxicol. Sci. (2004) [Pubmed]
  27. Mutagenic activity of ethylene oxide and propylene oxide under XPG proficient and deficient conditions in relation to N-7-(2-hydroxyalkyl)guanine levels in Drosophila. Nivard, M.J., Czene, K., Segerbäck, D., Vogel, E.W. Mutat. Res. (2003) [Pubmed]
  28. Evaluation of propylene oxide for mutagenic activity in 3 in vivo test systems. Hardin, B.D., Schuler, R.L., McGinnis, P.M., Niemeier, R.W., Smith, R.J. Mutat. Res. (1983) [Pubmed]
  29. Ultrathin coatings from isocyanate-terminated star PEG prepolymers: layer formation and characterization. Groll, J., Ameringer, T., Spatz, J.P., Moeller, M. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  30. Core electron transitions as a probe for molecular chirality: natural circular dichroism at the carbon K-edge of methyloxirane. Turchini, S., Zema, N., Zennaro, S., Alagna, L., Stewart, B., Peacock, R.D., Prosperi, T. J. Am. Chem. Soc. (2004) [Pubmed]
  31. Mutagenic activity of propylene oxide in bacterial and mammalian systems. Bootman, J., Lodge, D.C., Whalley, H.E. Mutat. Res. (1979) [Pubmed]
  32. A simple method for the preparation of cell cultures for ultrastructural investigation. Kuhn, H. J. Histochem. Cytochem. (1981) [Pubmed]
  33. Direct evidence for a soluble methane monooxygenase from type I methanotrophic bacteria: purification and properties of a soluble methane monooxygenase from Methylomonas sp. GYJ3. Shen, R., Yu, C., Ma, Q., Li, S. Arch. Biochem. Biophys. (1997) [Pubmed]
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