Detail of "67517-37-7"

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The synthesis, biological activity and metabolism of 15-[6,7-14C2]- and 15-[21-3H]-methyl retinone, 15-methyl retinol and 15-dimethyl retinol in rats

The synthesis, biological activity and metabolism of 15-[6,7-14C2]- and 15-[21-3H]-methyl retinone, 15-methyl retinol and 15-dimethyl retinol in rats. Tosukhowong, Pichit; Olson, James Allen (Fac. Sci., Mahidol Univ., Bangkok, Thailand). Biochim. Biophys. Acta, 529(3), 438-53 (English) 1978. CODEN: BBACAQ. ISSN: 0006-3002. DOCUMENT TYPE: Journal CA Section: 13 (Mammalian Biochemistry) Section cross-reference(s): 18 15-Methylretinone, 15-methylretinol, and 15-dimethylretinol were synthesized from all-trans-retinoic acid. The absorption max. and molar absorption coeffs. in EtOH are given. The latter 2 compds. showed fluorescence at 470 nm when excited around 320 nm, but with intensities 40 and 70%, resp., that of retinol. All reacted with F3CCO2H in CHCl3, and the alcs. were dehydrated in ethanolic HCl. Relative to all-trans-retinyl acetate, the biol. activities in rat growth assay were 15-methylretinone (4.7%), 15-methylretinol 16.2%), and 15-dimethylretinol (0.34%). The monomethyl derivs. actively supported testicular development and spermatogenesis, but none of the three analogs prevented degeneration of the retina in retinoate-treated vitamin A-deficient rats. By using [6,7-14C2]-, [11,12-3H2]- and [21-3H]-labeled analogs, the 15-methyl derivs. were shown to be well absorbed in the gut but poorly stored (1-3% of the dose) in the liver. Metabolites were excreted extensively (25-65%) in the bile, however, largely as glucuronides, and to some extent (15%) in the urine. 15-Methylretinone was reduced to 15-methylretinol in the intestinal mucosa but not in the liver, and fatty acyl esters of the alcs. were present in liver. 67517-37-7 which is the cas registry number is also used here. Apparently, none of these 15-methyl analogs is converted into retinol. Both monomethyl and dimethylretinol were transported in plasma in vivo in the retinol-binding protein fraction. The dosages required for half satn. and satn. of the plasma transport system were roughly inversely related to the biol. activities in growth. .