Vinylcyclohexene dioxide explained

4-Vinylcyclohexene dioxide (VCD) is an organic compound that contains two epoxide functional groups. It is industrially used as a crosslinking agent for the production of epoxy resins. It is a colourless liquid. It is an intermediate for synthesis of organic compounds.

Preparation and properties

4-Vinylcyclohexene dioxide is prepared by epoxidation of 4-vinylcyclohexene with peroxybenzoic acid.[1] Its viscosity is 15 mPa·s.

Safety

4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an alkylating agent.[1] VCD has toxic effects on fertility. It is a killer of oocytes, eggs in a female's ovaries, in immature ovarian follicles in mice and rats.[2] [3] [4]

In pest control, it has been used as an ovotoxic agent for reducing rat fertility.[5]

References

  1. Pham. Ha Q.. Marks. Maurice J.. Epoxy Resins. Ullmann's Encyclopedia of Industrial Chemistry. 10.1002/14356007.a09_547.pub2. 2005. 3-527-30673-0.
  2. Kappeler. Connie J.. Hoyer. Patricia B.. 2012-02-01. 4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity. Systems Biology in Reproductive Medicine. 58. 1. 57–62. 10.3109/19396368.2011.648820. 1939-6376. 3307534. 22239082.
  3. Takai. Yasushi. Canning. Jacqueline. Perez. Gloria I.. Pru. James K.. Schlezinger. Jennifer J.. Sherr. David H.. Kolesnick. Richard N.. Yuan. Junying. Flavell. Richard A.. 2003-01-01. Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo. Endocrinology. 144. 1. 69–74. 10.1210/en.2002-220814. 0013-7227. 12488331. free.
  4. Hoyer. P. B.. Devine. P. J.. Hu. X.. Thompson. K. E.. Sipes. I. G.. 2001-02-01. Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model. Toxicologic Pathology. 29. 1. 91–99. 0192-6233. 11215690. 10.1080/019262301301418892. 33667445.
  5. Toxicol Pathol. Jan–Feb 2001. 29. 1. 91–99. Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model. Hoyer PB, Devine PJ, Hu X, Thompson KE, Sipes IG. 10.1080/019262301301418892. 11215690. 33667445.

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