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Chemical Compound Review

U-5897     3-chloropropane-1,2-diol

Synonyms: Epibloc, Chlorhydrin, a-chlorohydrin, PubChem21311, u 5897, ...
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Disease relevance of Glycerol alpha-monochlorohydrin

  • An enzyme capable of dehalogenating vicinal haloalcohols to their corresponding epoxides was purified from the 3-chloro-1,2-propanediol-utilizing bacterium Arthrobacter sp. strain AD2 [1].
  • To investigate the relationship between sperm motion parameters and fertilizing ability, a model was developed to assess both of these endpoints synchronously using a toxicant that inhibits sperm motion. alpha-Chlorohydrin (ACH) was administered daily for 4 days to male hamsters at 0, 33, 49, 66, and 83 mg/kg body weight [2].
  • The antifertility activity and toxicity of alpha-chlorohydrin derivatives in male rats [3].
  • At a dose of 5 mg/kg injected intraperitoneally each day for 14 days, only alpha-chlorohydrin produced complete infertility [3].
  • The organisms E. coli, S. aureus, K. aerogenes, Pr. vulgaris and S. abortusovis were inhibited by 3-chloropropane-1,2-diol at high concentrations (ca 10,000 mug/ml) and Ps. aeruginosa was unaffected [4].

High impact information on Glycerol alpha-monochlorohydrin


Chemical compound and disease context of Glycerol alpha-monochlorohydrin


Biological context of Glycerol alpha-monochlorohydrin


Anatomical context of Glycerol alpha-monochlorohydrin


Associations of Glycerol alpha-monochlorohydrin with other chemical compounds


Gene context of Glycerol alpha-monochlorohydrin


Analytical, diagnostic and therapeutic context of Glycerol alpha-monochlorohydrin


  1. Purification and characterization of haloalcohol dehalogenase from Arthrobacter sp. strain AD2. van den Wijngaard, A.J., Reuvekamp, P.T., Janssen, D.B. J. Bacteriol. (1991) [Pubmed]
  2. Synchronous assessment of sperm motility and fertilizing ability in the hamster following treatment with alpha-chlorohydrin. Slott, V.L., Jeffay, S.C., Suarez, J.D., Barbee, R.R., Perreault, S.D. J. Androl. (1995) [Pubmed]
  3. The antifertility activity and toxicity of alpha-chlorohydrin derivatives in male rats. Brown-Woodman, P.D., White, I.G., Ridley, D.D. Contraception. (1979) [Pubmed]
  4. Influence of 3-chloropropane-1,2-diol on microbial lipid composition and its effect on the activity of some antibacterial agents. Bulman, R.A., Stretton, R.J. Microbios (1975) [Pubmed]
  5. Identification of the biochemical lesion produced by alpha-chlorohydrin in spermatozoa. Mohri, H., Suter, D.A., Brown-Woodman, P.D., White, I.G., Ridley, D.D. Nature (1975) [Pubmed]
  6. Focal astrocyte loss is followed by microvascular damage, with subsequent repair of the blood-brain barrier in the apparent absence of direct astrocytic contact. Willis, C.L., Nolan, C.C., Reith, S.N., Lister, T., Prior, M.J., Guerin, C.J., Mavroudis, G., Ray, D.E. Glia (2004) [Pubmed]
  7. Reversible disruption of tight junction complexes in the rat blood-brain barrier, following transitory focal astrocyte loss. Willis, C.L., Leach, L., Clarke, G.J., Nolan, C.C., Ray, D.E. Glia (2004) [Pubmed]
  8. The effects of drugs on sperm. Drife, J.O. Drugs (1987) [Pubmed]
  9. Effects of antifertility drugs on epididymal protein secretion, acquisition of sperm surface proteins and fertility in male rats. Tsang, A.Y., Lee, W.M., Wong, P.Y. Int. J. Androl. (1981) [Pubmed]
  10. Acute energy deprivation syndromes: investigation of m-dinitrobenzene and alpha-chlorohydrin toxicity on immortalized rat brain microvessel endothelial cells. Romero, I.A., Rist, R.J., Chan, M.W., Abbott, N.J. Neurotoxicology (1997) [Pubmed]
  11. Comparative testicular toxicities of two isomers of dichloropropanol, 2,3-dichloro-1-propanol, and 1,3-dichloro-2-propanol, and their metabolites alpha-chlorohydrin and epichlorohydrin, and the potent testicular toxicant 1,2-dibromo-3-chloropropane. Omura, M., Hirata, M., Zhao, M., Tanaka, A., Inoue, N. Bulletin of environmental contamination and toxicology. (1995) [Pubmed]
  12. Comparative disposition of 2,3-epoxy-1-propanol (glycidol) in rats following oral and intravenous administration. Nomeir, A.A., Silveira, D.M., Ferrala, N.F., Markham, P.M., McComish, M.F., Ghanayem, B.I., Chadwick, M. Journal of toxicology and environmental health. (1995) [Pubmed]
  13. Mode of action of alpha-chlorohydrin as a male anti-fertility agent. Inhibition of the metabolism of ram spermatozoa by alpha-chlorohydrin and location of block in glycolysis. Brown-Woodman, P.D., Mohri, H., Mohri, T., Suter, D., White, I.G. Biochem. J. (1978) [Pubmed]
  14. Fertilizing ability in vivo and in vitro of spermatozoa of rats and mice treated with alpha-chlorohydrin. Tsunoda, Y., Chang, M.C. J. Reprod. Fertil. (1976) [Pubmed]
  15. Determination of rate constants and activation energy of 3-chloro-1,2-propanediol hydrolysis by capillary electrophoresis with electrochemical detection. Xing, X., Cao, Y., Wang, L. Journal of chromatography. A. (2005) [Pubmed]
  16. Futile substrate cycles in the glycolytic pathway of boar and rat spermatozoa and the effect of alpha-chlorohydrin. Ford, W.C., Harrison, A. J. Reprod. Fertil. (1987) [Pubmed]
  17. Studies on the rat epididymal blood vessels following alpha-chlorohydrin administration. Reijonen, K., Kormano, M., Ericsson, R.J. Biol. Reprod. (1975) [Pubmed]
  18. Effects of alpha-chlorohydrin on the testes and epididymides of dog: a preliminary study. Dixit, V.P., Lohiya, N.K., Agawal, M. Fertil. Steril. (1975) [Pubmed]
  19. Proceedings: Decrease in the glycerylphosphorylcholine content of the epididymis after injecting alpha-chlorohydrin into rats. Morris, S., Brown-Woodman, P.D., White, I.G. J. Reprod. Fertil. (1976) [Pubmed]
  20. The male antifertility agents alpha chlorohydrin, 5-thio-D-glucose, and 6-chloro-6-deoxy-D-glucose interfere with sugar transport across the epithelium of the rat caput epididymidis. Hinton, B.T., Hernandez, H., Howards, S.S. J. Androl. (1983) [Pubmed]
  21. The entry of alpha-chlorohydrin into body fluids of male rats and its effect upon the incorporation of glycerol into lipids. Edwards, E.M., Jones, A.R., Waites, G.M. J. Reprod. Fertil. (1975) [Pubmed]
  22. Glucose regulation of guinea-pig sperm motility. Mújica, A., Moreno-Rodríguez, R., Naciff, J., Neri, L., Tash, J.S. J. Reprod. Fertil. (1991) [Pubmed]
  23. Effects of the optical isomers of alpha-chlorohydrin on glycolysis by ram testicular spermatozoa and the fertility of male rats. Ford, W.C., Harrison, A., Waites, G.M. J. Reprod. Fertil. (1977) [Pubmed]
  24. The vicinal chloroalcohols 1,3-dichloro-2-propanol (DC2P), 3-chloro-1,2-propanediol (3CPD) and 2-chloro-1,3-propanediol (2CPD) are not genotoxic in vivo in the wing spot test of Drosophila melanogaster. Frei, H., Würgler, F.E. Mutat. Res. (1997) [Pubmed]
  25. The activity of glyceraldehyde 3-phosphate dehydrogenase in spermatozoa from different regions of the epididymis in laboratory rodents treated with alpha-chlorohydrin or 6-chloro-deoxyglucose. Ford, W.C., Harrison, A. J. Reprod. Fertil. (1983) [Pubmed]
  26. Effect of sodium nitrite on the alpha-chlorohydrin-induced lesion of the testis--epididymis complexin the rat. Kalla, N.R., Singh, B. J. Reprod. Fertil. (1979) [Pubmed]
  27. Comparative study of the molecular species of chloropropanediol diesters and triacylglycerols in milk fat. Kuksis, A., Marai, L., Myher, J.J., Cerbulis, J., Farrell, H.M. Lipids (1986) [Pubmed]
  28. Qualitative and quantitative changes of acetylcholinesterase in the central nervous system of mice during low and high dose treatment of alpha-chlorohydrin. Kakaria, V.K., Sood, P.P. Cell. Mol. Biol. (1985) [Pubmed]
  29. The action of (R)- and (S)-alpha-chlorohydrin and their metabolites on the metabolism of boar sperm. Stevenson, D., Jones, A.R. Int. J. Androl. (1984) [Pubmed]
  30. Differences in sperm motion between high- and low-shuttlebox avoidance rats (Hatano strains). Sato, M., Ohta, R., Kojima, K., Shirota, M. J. Androl. (2002) [Pubmed]
  31. Gas-liquid chromatography of 3-chloropropanediol. Rodman, L.E., Ross, R.D. J. Chromatogr. (1986) [Pubmed]
  32. Antifertility and toxicological studies with aromatic esters of alpha-chlorohydrin in male rats. Rooney, F.R., Jackson, H. Chem. Biol. Interact. (1980) [Pubmed]
  33. Improved risk assessment by screening sperm parameters. Plassmann, S., Urwyler, H. Toxicol. Lett. (2001) [Pubmed]
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