Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Ubiquinone and Related Compounds. XXXI. Synthesis of Urinary Metabolites of Ubiquinone, Phylloquinone, α-Tocopherol and Their Related Compounds
MASAZUMI WATANABEKAYOKO OKAMOTOISUKE IMADAHIROSHI MORIMOTO
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1978 Volume 26 Issue 3 Pages 774-783

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Abstract
Metabolites (XVIIa, b, c) of ubiquinone, phylloquinone and α-tocopherol, and their 2', 3'-dihydro (XXa, b, c), dicarboxy (XVIa, b, XXIIIa, b, c, XXIVa, b and XXVa, b) and 3'-demethyl (XXIa, b) derivatives were synthesized. During the synthetic studies of these compounds, we found that cis-4-acetoxy-1-bromo-2-methyl-2-butene (cis-III) was more reactive to nucleophiles than the corresponding trans isomer. γ-Vinyl-γ-butyrolactone (XII), which was a useful starting material for the synthesis of XXIa, b, was synthesized in one step from 1, 3-butadiene. The 3'-methyl group of XVIIa, b was not essential for the membrane-stabilizing activity in the rat-liver lysosome. Introduction of a carboxyl but not a carboxyl ester group into XVIIa, b resulted in a loss of the stabilizing activity.
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