121358-45-0Relevant academic research and scientific papers
Cheap synthetic method of ethyl vanillin beta-D-glucopyranoside
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Paragraph 0028; 0035; 0040; 0043; 0044; 0045, (2018/07/30)
The invention discloses a cheap synthetic method of ethyl vanillin beta-D-glucopyranoside. Alpha-bromotetraacetyl glucose and ethyl vanillin react at 20-80 DEG C under the condition of water-free andalkaline conditions to form ethyl vanillin tetra-O-acety
Molecular interactions between Barley and Oat β-glucans and phenolic derivatives
Simonsen, Henrik Toft,Nielsen, Mette S.,Christensen, Niels J.,Christensen, Ulla,Cour, Thomas V. La,Motawia, Mohammed Saddik,Jespersen, Birthe P.M.,Engelsen, Soren B.,Moller, Birger Lindberg
experimental part, p. 2056 - 2064 (2010/07/02)
Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats. The two β-glucan products showed very similar binding properties. It was demonstrated that the two β-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the β-glucans. When the barley β-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
Convenient Multigram Scale Glycosylations of Scented Alcohols Employing Phase-Transfer Reactions
Kroeger, Lars,Thiem, Joachim
, p. 9 - 24 (2007/10/03)
Various conditions for glycosylation (Koenigs-Knorr, Helferich, trichloroacetimidate, Fischer-Raske, phase-transfer methods) of 3-ethoxy-4-hydroxybenzaldehyde (ethyl vanillin), 3-hydroxy-2-methyl-4-pyranone (maltol) and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (furaneol(R)) were evaluated, taking into account yields and ease of preparation (e.g., utilized donor, catalyst, conditions). The best results were achieved employing phase transfer catalysis in a two-phase solvent mixture. To increase water solubility for better applicability, the hitherto unknown maltosides of the corresponding alcohols were synthesized, again proving the value of phase-transfer conditions for glycosylation of phenols.
Synthesis and Antiinflammatory Activity of Some Glycosidated 3-Methylpyrazolin-5-(4H)-one-4-benzylidenes
Jain, S. M.,Devi, Sunita,Bani, S.,Singh, Surjit,Singh, G. B.
, p. 1019 - 1023 (2007/10/02)
The substituted hydroxybenzaldehyde 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides (IIA-H), obtained by the stereospecific synthesis using phase transfer catalysis, on condensation with 3-methylpyrazolin-5-(4H)-one in the presence of piperidine yield the title compounds (IIIA-H).The effect of various phase transfer catalysts has been studied during the preparation of II.Compounds III have been tested for their antiinflammatory activity.
