The metabolism of cis- and trans-decalin.
1. The metabolism of cis- and trans-decalin in the rabbit has been investigated. 2. Both hydrocarbons were oxidized to racemic secondary alcohols and excreted as ether glucuronides in amounts equal to about 60% of the dose administered. The principal glucuronides were isolated as triacetyl methyl esters and as sodium salts. 3. cis-Decalin gave rise mainly to (+/-)-cis-cis-2-decalol, together with a little cis-trans-2-decalol, and trans-decalin mainly to (+/-)-trans-cis-2-decalol and a small amount of trans-trans-2-decalol. 4. These results suggest that biological oxidation of the decalins does not occur via a free-radical mechanism. An attempt is made to explain why racemic alcohols are obtained, rather than the more typical optically active products of enzymic reaction, and a mechanism is proposed. It is suggested that enzymes similar to steroid hydroxylases are involved.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D005260:Female; D005965:Glucuronates / Q000378:metabolism; D009281:Naphthalenes / Q000378:metabolism*; D011817:Rabbits
D005965:Glucuronates; D009281:Naphthalenes