DICUMAROL-2-C14: SYNTHESIS AND METABOLISM STUDIES

Abstract
Dicumarol (3,3′-methylene bis(4-hydroxycoumarin)) has been synthesized labeled with C14 in the 2-position. Starting with active barium carbonate of specific activity 1.6 µc.per mgm., the intermediate compounds diethyl carbonate-1-C14 and 4-hydroxycoumarin-2-C14 were prepared. Subsequent reaction of the latter compound with aqueous formaldehyde yielded dicumarol-2-C14. The specific activity of the final product, once recrystallized from cyclohexanone, was 4.3 × 105 counts per min. per mgm. corrected for geometry and absorption. The expired carbon dioxide from a mouse injected with this C14-labeled product was collected and found to contain no radioactivity. This indicated that, in this animal, the 2-carbon of dicumarol does not enter into a metabolic process whereby it is expired as carbon dioxide.

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