116718-17-3Relevant articles and documents
Oligomeric Isoflavonoids. Part 2. Structure and Synthesis of Xanthocercin A and B, the First Isoflavono-lignoids
Bezuidenhout, S. Catherine,Bezuidenhout, Barend C. B.,Brandt, E. Vincent,Ferreira, Daneel
, p. 1237 - 1242 (2007/10/02)
The structure of xanthocercin A and B, the first isoflavono-lignoids, have been established as 2,3-trans-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-hydroxymethyl-2,3-dihydro-7H-1,4-dioxinochromen-7-one (1) and 2,3-trans-8-(3-hydroxy-4-methoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-2,3-dihydro-7H-1,4-dioxinochromen-7-one (3) respectively by spectroscopic methods.These structures have been confirmed by synthesis via phenol oxidative coupling of the appropriate 7,8-dihydroxyisoflavone and respectively sinapyl and coniferyl alcohol.The natural occurrence of xanthocercin A and B as single regioisomers and their regiospecific formation during synthesis presumably originate from marked differences in susceptibility to oxidation of the hydroxy functions in their 'catechol precursors'.