494-08-6Relevant articles and documents
Glycosylation of vanillin by amyloglucosidase in organic media
Sivakumar, Ramaiah,Divakar, Soundar
, p. 695 - 699 (2006)
Glycosylation of vanillin using amyloglucosidase from a Rhizopus mold with D-glucose, D-galactose, D-mannose, maltose, sucrose and D-sorbitol in di-isopropyl ether yielded glycosides in the range 13-53%. NMR spectral data confirmed linking between the phenolic OH of vanillin and C1 and/or C6 of the carbohydrate moieties.
Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme
Alvarenga, Dalila Junqueira,Carvalho, Diogo Teixeira,Cordeiro, Cleydson Finotti,Dias, Danielle Ferreira,Matias, Laira Maria Faria,Souza, Thiago Belarmino de,Lavorato, Stefania Neiva,Pereira, Marília Gabriella Alves Goulart
, (2020/10/15)
We report here a series of glucosides which are active as inhibitors of the angiotensin converting enzyme (ACE). They are structurally related to the natural compound eugenol and exhibited significant inhibition values. Their syntheses were expeditious and we could obtain informative docking plots of them complexed to this enzyme. A glucoside derived from eugenol, carrying a carboxylic group in the aglycone, was the most active of them (with an IC50 of 0.4 mM) and showed good binding energies in docking studies with ACE. Moreover, computational prediction of toxicity risks, physicochemical properties and drug score show that the glucoside derivative of eugenol is a suitable compound for optimisation studies aimed at finding new drug candidates.
Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
Yan, Shiqiang,Ren, Sumei,Ding, Ning,Li, Yingxia
, p. 41 - 46 (2018/03/09)
Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.