The metabolism of cis- and trans-indane-1,2-diol

Abstract

1. The metabolism of cis-indane-1,2-diol, trans-indane-1,2-diol, indene epoxide and 2-hydroxyindan-1-one in rats has been studied. The substances were administered to the animals by subcutaneous injection. 2. The urine of the dosed animals was examined for the presence of free and conjugated cis- and trans-dihydrodiols, and for each compound it was possible to isolate both cis and trans forms of indane-1,2-diol from the urine. 3. The urines were also examined by paper chromatography for ketones and two ketonic metabolites were detected in the urine of rats dosed separately with cis-indane-1,2-diol, trans-indane-1,2-diol, 2-hydroxyindan-1-one and indene epoxide. The ketones were provisionally identified as (1-oxoindan-2-yl glucosid)uronic acid and 1-oxoindan-2-yl sulphuric acid. 4. (1-Oxoindan-2-yl glucosid)uronic acid was isolated as the 2,4-dinitrophenylhydrazone from the urine of rats dosed separately with cis-indane-1,2-diol and trans-indane-1,2-diol. 5. Possible mechanisms for the interconversion of cis- and trans-indane-1,2-diol are discussed.

Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation and metabolism of epoxides related to benzo[a]pyrene and to 7,8- and 9,10-dihydrobenzo[a]pyrene

“…However, both indene (Brook&Youngs, 1956)andacenaphthylene (Hopkins et al, 1962) are metabolized in rats to mixtures of cis-and trans-dihydroxy compounds. Indene epoxide is similarly metabolized by rats into a mixture of the 1972 cis-and trans-dihydroxy compounds (Lewis, 1966) and, like the oxides (V and XIV), it is also converted chemically into a mixture of isomers. With rat liver microsomal fractions, however, indene and indene epoxide are both converted into the trans-dihydroxy compound only (Leibman & Ortiz, 1968).…”