4-Oxoretinal
IUPAC 名称
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
描述
4-Oxoretinal is a predominant retinoids during morphogenesis in mouse skin in vivo. Topical 4-oxoretinal and 4-oxoretinol promoted significant epidermal hyperplasia and metaplasia in mouse tail. They induced a moderate response for epidermal inflammation, compared with retinal, whereas neither 4-oxoretinal nor 4-oxoretinol prevented menadione-induced epidermal lipid peroxidation, unlike retinal and retinol. As analyzed by quantitative PCR, 4-oxoretinal and 4-oxoretinol did not reproduce the significant increased expression of genes coding for keratin 4, amphiregulin, heparin-EGF and CYP26A1, that did induce retinal and retinol. However, both retinal and 4-oxoretinal significantly inhibited the lipopolysaccharide-induced maturation of human dendritic cells in vitro. As analyzed in vivo and in vitro, 4-oxoretinal and 4-oxoretinol were not converted into retinoic acid. We conclude that 4-oxoretinal and 4-oxoretinol exert a moderate direct retinoid-like activity in vivo, thus confirming previous in vitro studies in amphibians showing 4-oxometabolites of vitamin A as bioactive agents rather than inactive catabolites. [HMDB]
异构
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O
InChI标识符
InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+
键
ZORDCCAUKPDLPN-ZBSJWCJSSA-N