chlorohydrin affects the efferent ducts and caput epididymis

Conversion of a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin

The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of a superatmospheric partial pressure of hydrogen chloride for a sufficient time and at a sufficient temperature, and wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts. In addition, certain catalysts of the present invention may be used in the present process at superatmospheric, atmospheric and subatmospheric pressure conditions with improved results.

The antifertility actions of α-chlorohydrin in the male

It seems probable that α-chlorohydrin enters sperm cells, competes with glycerol (52) for glycerol kinase (23) and becomes phosphorylated, the product, α-chlorohydrin phosphate, being an inhibitor of glyceraldehyde-3-phosphate dehydrogenase (57). The rate of sperm glycolysis and the concentration of ATP (54) are reduced with sperm motility declining (44, 45, 46) to such an extent that fertilization cannot be successful. In higher doses, α-chlorohydrin affects the efferent ducts and caput epididymis (60) by an unknown mechanism leading to an occlusion preventing the passage of testicular sperm to the epididymis. This action leads to prolonged or even permanent infertility. The inactivity of α-chlorohydrin in some species may be due to the inability of the compound to gain access to the sperm across an epididymal barrier (12, 32) and strain differences in susceptibility could be accounted for by degrees in the rates of metabolism and/or excretion