Disease relevance of Izoforon

• In male mice, isophorone exposure may have been associated with an increase in hepatocellular neoplasms and mesenchymal neoplasms of the integumentum in high dose animals, and with a marginally increased incidence of lymphoma in low dose male mice [1].
• Toxicity of acenaphthene and isophorone to early life stages of fathead minnows [2].
• Toxicology and carcinogenesis studies of isophorone were conducted by administering 0, 250, or 500 mg/kg body weight per day by gavage in corn oil to groups of 50 F344/N rats and 50 B6C3F1 mice of each sex, 5 days/week, for 103 weeks [1].

High impact information on Izoforon

• We have studied the proline-directed, Pd-catalyzed enantioselective hydrogenation of isophorone in the liquid state using a variety of methods [3].
• Racemic 3,3,5-trimethylcyclohexanone (TMCH) is produced by initial heterogeneous hydrogenation of isophorone; proline then reacts homogeneously, preferentially with one enantiomer of TMCH, leaving an excess of the other [3].
• Binding of d-limonene and 1,4-dichlorobenzene to alpha 2u-globulin did not alter the degradation of the protein, whereas binding of d-limonene-1,2-oxide, 2.5-dichlorophenol, and isophorone decreased alpha 2u-globulin degradation by 33% [4].
• Chlorination of millimolar concentrations of isophorone generated mutagens at a pH as low as 8.5, while mutagens were formed from submillimolar concentrations of mesityl oxide at pH 8.5, or millimolar concentrations at pH 7 [5].
• In continuation of our SAR-studies of sandalwood odorants four isophorone analogues of beta-santalol have been synthesized [6].

Biological context of Izoforon

• Toxicology and carcinogenesis studies of isophorone in F344 rats and B6C3F1 mice [1].
• Isophorone was shown to be significantly attractive to sea lice when placed in a slow-release system in a perfused tank of seawater in a choice situation [7].

Anatomical context of Izoforon

• Perturbation of reproductive tract glutathione by isophorone treatment significantly enhanced the extent of 3H-EMS-induced binding to sperm heads [8].
• The ability of isophorone to enhance the covalent binding of tritiated ethyl methanesulfonate (3H-EMS) to spermatocytes was assessed [8].

Associations of Izoforon with other chemical compounds

• Our results unambiguously reveal the true reaction pathway and demonstrate that all earlier mechanistic hypotheses are wrong: although a proline/isophorone condensation product is formed, it is merely a spectator and not a key reaction intermediate in subsequent heterogeneous hydrogenation [3].

References