3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → 7,4'-Dihydroxy-3'-methoxyflavanone

반응식

[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][C:21]=1[OH:22])[CH:14]=[CH:15][C:16](O)=[O:17].OS(O)(=O)=O>C1COCC1>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:16](=[O:17])[CH2:15][CH:14]([C:13]3[CH:19]=[CH:20][C:21]([OH:22])=[C:11]([O:10][CH3:9])[CH:12]=3)[O:5]2)=[CH:7][CH:8]=1

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실험 절차

Resorcinol (15), 3-methoxy-4-hydroxy-cinnamic acid (16) and H2SO4 (5%) were refluxed in THF for 4 hours to provide 7,4′-dihydroxy-3′-methoxy flavanone (17) (90% yield). The product, 7,4′-dihydroxy-3′-methoxy flavanone (17) was then treated with 10% sodium hydroxide at 80° C. for 1 hour, followed by reduction with sodium borohydride in propanol to provide, as confirmed LC-MS/PDA detection, 1-(2,4-dihydroxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol (19). The crude product exhibits quite strong tyrosinase inhibitory activity. The mixture was further purified by HTP.