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Chemical Compound Review

4-vinylcyclohexene     4-ethenylcyclohexene

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Disease relevance of 4-vinylcyclohexene


High impact information on 4-vinylcyclohexene


Biological context of 4-vinylcyclohexene

  • The stereochemical course of the biotransformation of 4-vinylcyclohexene (VCH, 1) by liver microsomes from male and female control and induced rats and purified rat P450 2B1 and 2E1 has been determined [6].
  • The metabolites, cis- and trans-4-vinylcyclohexene 1,2-epoxide (2 and 3, respectively) and the isomeric 4-vinylcyclohexene 7,8-epoxides (4 and 5), were rapidly biotransformed into the corresponding vicinal diols by mEH-catalyzed hydrolysis [6].
  • Rats are exposed to repeated daily dosing (20 days) with 4-vinylcyclohexene diepoxide (VCD) to cause early ovarian failure (model for postmenopause), and ovaries are directly exposed to 7,12-dimethylbenz(a)anthracene (DMBA) to cause abnormal ovarian proliferation and neoplasia [7].
  • Repeated dosing of rats with the ovotoxic chemical, 4-vinylcyclohexene diepoxide (VCD), destroys primordial and primary ovarian follicles via apoptosis (physiological cell death) by accelerating the normal rate of atresia [8].
  • OBJECTIVE: To determine whether the 4-vinylcyclohexene diepoxide (VCD)-treated mouse menopause model, which involves accelerated atresia of primordial follicles and induces gradual ovarian failure (while sparing the ovarian stroma), can be adapted to nonhuman primates [9].

Anatomical context of 4-vinylcyclohexene


Associations of 4-vinylcyclohexene with other chemical compounds


Gene context of 4-vinylcyclohexene


Analytical, diagnostic and therapeutic context of 4-vinylcyclohexene


  1. 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]
  2. Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo. Takai, Y., Canning, J., Perez, G.I., Pru, J.K., Schlezinger, J.J., Sherr, D.H., Kolesnick, R.N., Yuan, J., Flavell, R.A., Korsmeyer, S.J., Tilly, J.L. Endocrinology (2003) [Pubmed]
  3. 17beta-estradiol affords protection against 4-vinylcyclohexene diepoxide-induced ovarian follicle loss in Fischer-344 rats. Thompson, K.E., Sipes, I.G., Greenstein, B.D., Hoyer, P.B. Endocrinology (2002) [Pubmed]
  4. The biochemical basis for the species difference in hepatic microsomal 4-vinylcyclohexene epoxidation between female mice and rats. Smith, B.J., Sipes, I.G., Stevens, J.C., Halpert, J.R. Carcinogenesis (1990) [Pubmed]
  5. Stereochemical aspects in the 4-vinylcyclohexene biotransformation with rat liver microsomes and purified cytochrome P450s: diepoxide formation and hydrolysis. Chiappe, C., De Rubertis, A., Piegari, G., Amato, G., Gervasi, P.G. Chem. Res. Toxicol. (2003) [Pubmed]
  6. Stereochemical aspects in the 4-vinylcyclohexene biotransformation with rat liver microsomes and purified p450s. monoepoxides and diols. Chiappe, C., De Rubertis, A., De Carlo, M., Amato, G., Gervasi, P.G. Chem. Res. Toxicol. (2001) [Pubmed]
  7. Dual modality imaging of a novel rat model of ovarian carcinogenesis. Kanter, E.M., Walker, R.M., Marion, S.L., Brewer, M., Hoyer, P.B., Barton, J.K. Journal of biomedical optics. (2006) [Pubmed]
  8. A single dose of the ovotoxicant 4-vinylcyclohexene diepoxide is protective in rat primary ovarian follicles. Borman, S.M., VanDePol, B.J., Kao, S., Thompson, K.E., Sipes, I.G., Hoyer, P.B. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  9. Destruction of primordial ovarian follicles in adult cynomolgus macaques after exposure to 4-vinylcyclohexene diepoxide: a nonhuman primate model of the menopausal transition. Appt, S.E., Kaplan, J.R., Clarkson, T.B., Cline, J.M., Christian, P.J., Hoyer, P.B. Fertil. Steril. (2006) [Pubmed]
  10. Epoxidation of 4-vinylcyclohexene by human hepatic microsomes. Smith, B.J., Sipes, I.G. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  11. Effect of 4-vinylcyclohexene on micronucleus formation in the bone marrow of rats and mice. Bevan, C., Keller, D.A., Panepinto, A.S., Bentley, K.S. Drug and chemical toxicology. (2001) [Pubmed]
  12. Carcinogencity bioassays of bisphenol A, 4-vinylcyclohexene diepoxide, and 4-vinycyclohexene. Huff, J. Toxicol. Sci. (2001) [Pubmed]
  13. Activation of mitogen-activated protein kinases and AP-1 transcription factor in ovotoxicity induced by 4-vinylcyclohexene diepoxide in rats. Hu, X., Flaws, J.A., Sipes, I.G., Hoyer, P.B. Biol. Reprod. (2002) [Pubmed]
  14. Apoptosis induced in rats by 4-vinylcyclohexene diepoxide is associated with activation of the caspase cascades. Hu, X., Christian, P.J., Thompson, K.E., Sipes, I.G., Hoyer, P.B. Biol. Reprod. (2001) [Pubmed]
  15. Role of induction of specific hepatic cytochrome P450 isoforms in epoxidation of 4-vinylcyclohexene. Fontaine, S.M., Hoyer, P.B., Halpert, J.R., Sipes, I.G. Drug Metab. Dispos. (2001) [Pubmed]
  16. Induction of cytochrome P-450 enzymes after repeated exposure to 4-vinylcyclohexene in B6C3F1 mice. Doerr-Stevens, J.K., Liu, J., Stevens, G.J., Kraner, J.C., Fontaine, S.M., Halpert, J.R., Sipes, I.G. Drug Metab. Dispos. (1999) [Pubmed]
  17. Toxicological evaluation of 4-vinylcyclohexene. II. Induction of ovarian tumors in female B6C3F1 mice by chronic oral administration of 4-vinylcyclohexene. Collins, J.J., Montali, R.J., Manus, A.G. Journal of toxicology and environmental health. (1987) [Pubmed]
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