94930-83-3Relevant academic research and scientific papers
Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
Dong, Hongbo,Du, Weihong,He, Yujiao,Shi, Zheng,Wang, Yingying,Wu, Min
, p. 2866 - 2874 (2021/11/12)
Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.
Synthesis and Reactivity of Vinyl Quinone Methides
Zanarotti, Antonio
, p. 941 - 945 (2007/10/02)
Vinyl quinone methides 4a and 4b were obtained in high yields by Ag2O oxidation of eugenol (3a) and of 2,6-dimethoxy-4-(2-propenyl)phenol (3b).Vinyl quinone methides (VQMs) reacted with alcohols, with phenols, and with acetic acid giving compounds 5 and 6.As the former rearranged to the latter in the reaction medium, the addition of the reported substrates to VQMs turned out to be wholly regioselective toward the formation of coniferyl and sinapyl derivatives 6.In contrast, addition of carbon nucleophiles (acetylacetone and EtNO2) to VQMs gave both compounds 7 and 8.By reaction of the acetates 6a and 6b (CR=CH3CO) with LiAlH4 it was possible to perform a novel synthesis of coniferyl and sinapyl alcohols (1a and 1b).Treatment of the same acetates with an aqueous solution of NaHCO3 reproduced VQMs 4, which by subsequent reduction with NaBH4, gave propenylphenols 2 and allylphenols 3.Formation of the latter compounds from coniferyl and sinapyl acetates via VQM is here proposed as a possible biosynthetic pathway.
PREPARATION AND REACTIVITY OF 2,6-DIMETHOXY-4-ALLYLIDENE-2,5-CYCLOHEXADIEN-1-ONE (VINYL QUINONE METHIDE) A NOVEL SYNTHESIS OF SINAPYL ALCOHOL
Zanarotti, A.
, p. 3815 - 3818 (2007/10/02)
Title compound (3b), prepared in concentrated CHCl3 or benzene solution and spectroscopically characterized, is shown to be an useful intermediate for the synthesis of sinapyl alcohol (1b) and its derivatives.
