COMPARISON OF THE MUTAGENICITIES OF MALONDIALDEHYDE AND THE SIDE PRODUCTS FORMED DURING ITS CHEMICAL SYNTHESIS

  • 1 January 1980
    • journal article
    • research article
    • Vol. 40  (2) , 276-282
Abstract
Malondialdehyde, a product of polyunsaturated fatty acid metabolism and degradation, has been reported to be mutagenic and carcinogenic. The malondialdehyde used for testing was generated by the acidic hydrolysis of tetraalkoxypropanes. The production of compounds mutagenic to Salmonella typhimurium strain his D 3052 following the hydrolysis of tetraalkoxypropanes was studied. The major mutagenic compound produced from tetraethoxyproprane is .beta.-ethoxy-acrolein (90-100 revertants/.mu.mol) and not malondialdehyde (3-5 revertants/.mu.mol). Hydrolysis of tetramethoxypropane produces 2 compounds, .beta.-methoxy-acrolein (125-160 revertants/.mu.mol) and 3,3-dimethoxypropionaldehyde (105-135 revertants/.mu.mol), which are more mutagenic than is malondialdehyde. Using standard conditions for the hydrolysis of tetraethoxypropane, the yield of malondialdehyde is 25%, and the yield of .beta.-ethoxyacrolein is 13%. Considering the differences in specific mutagenicity, the compound which accounts for the bulk of the mutagenicity of a crude hydrolysate of tetraethoxypropane is not malondialdehyde. The presence of these incomplete hydrolysis products may lead to a substantial overestimation of the actual mutagenicity and carcinogenicity of malondialdehyde.