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Chemical Compound Review:

CCRIS 1422 4-ethenylcyclohexene

Synonyms: LS-302, NCI-C54999, AG-D-05429, AG-K-82796, ACMC-209smd, ...

Pullinger, D.H. et al., Fontaine, S.M. et al., Randerath, K. et al., Mabon, N. et al., Watabe, T. et al., et al.

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Disease relevance of CCRIS 1422

Toxicity of 4-vinyl-1-cyclohexene diepoxide after 13 weeks of dermal or oral exposure in rats and mice [1].

High impact information on CCRIS 1422

Accelerated ovarian failure induced by 4-vinyl cyclohexene diepoxide in Nrf2 null mice [2].
Metabolism of the carcinogenic bifunctional olefin oxide, 4-vinyl-1-cyclohexene dioxide, by hepatic microsomes [3].
Reduced ability of rat preantral ovarian follicles to metabolize 4-vinyl-1-cyclohexene diepoxide in vitro [4].
4-Vinyl-1-cyclohexene (VCH), is converted by multiple forms of cytochrome P450 (CYP) to two monoepoxides (4-vinyl-1-cyclohexene 1,2-epoxide [VCH-1,2-epoxide], 4-vinyl-1-cyclohexene 7,8-epoxide [VCH-7,8-epoxide]), and 4-vinyl-1-cyclohexene diepoxide (VCD) [5].
4-Vinyl-1-cyclohexene diepoxide (VCD), and industrial chemical, and its parent compound, 4-vinyl-1-cyclohexene (VCH), are potential health hazards, a they destroy oocytes in follicles in rodents [6].

Biological context of CCRIS 1422

Infrared and gas chromatographic analytical methods were adapted for monitoring the concentration and distribution of butadiene in exposure chambers, and for analysis of known impurities, particularly, t-butyl catechol and 4-vinyl-1-cyclohexene, in atmospheres generated for inhalation tests [7].

Anatomical context of CCRIS 1422

4-vinyl-1-cyclohexene diepoxide (VCD) is known to destroy oocytes in ovaries of immature rats [8].

Associations of CCRIS 1422 with other chemical compounds

32P-postlabeling of 1,3-butadiene and 4-vinyl-1-cyclohexene metabolite-DNA adducts: in vitro and in vivo applications [9].

References

Toxicity of 4-vinyl-1-cyclohexene diepoxide after 13 weeks of dermal or oral exposure in rats and mice. Chhabra, R.S., Elwell, M.R., Peters, A. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1990) [Pubmed]
Accelerated ovarian failure induced by 4-vinyl cyclohexene diepoxide in Nrf2 null mice. Hu, X., Roberts, J.R., Apopa, P.L., Kan, Y.W., Ma, Q. Mol. Cell. Biol. (2006) [Pubmed]
Metabolism of the carcinogenic bifunctional olefin oxide, 4-vinyl-1-cyclohexene dioxide, by hepatic microsomes. Watabe, T., Sawahata, T. Biochem. Pharmacol. (1976) [Pubmed]
Reduced ability of rat preantral ovarian follicles to metabolize 4-vinyl-1-cyclohexene diepoxide in vitro. Flaws, J.A., Salyers, K.L., Sipes, I.G., Hoyer, P.B. Toxicol. Appl. Pharmacol. (1994) [Pubmed]
Evaluation of hepatic cytochrome P4502E1 in the species-dependent bioactivation of 4-vinylcyclohexene. Fontaine, S.M., Hoyer, P.B., Sipes, I.G. Life Sci. (2001) [Pubmed]
In vitro and in vivo (32)P-postlabeling analysis of 4-vinyl-1-cyclohexene (butadiene dimer) diepoxide-DNA adducts. Randerath, K., Mabon, N. Cancer Lett. (1996) [Pubmed]
Inhalation toxicity studies with 1,3-butadiene -- 1. Atmosphere generation and control. Pullinger, D.H., Crouch, C.N., Dare, P.R. American Industrial Hygiene Association journal. (1979) [Pubmed]
Destruction of preantral follicles in adult rats by 4-vinyl-1-cyclohexene diepoxide. Flaws, J.A., Doerr, J.K., Sipes, I.G., Hoyer, P.B. Reprod. Toxicol. (1994) [Pubmed]
32P-postlabeling of 1,3-butadiene and 4-vinyl-1-cyclohexene metabolite-DNA adducts: in vitro and in vivo applications. Mabon, N., Randerath, K. Toxicology (1996) [Pubmed]

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