72500-10-8Relevant academic research and scientific papers
GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS
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Paragraph 0241-0242, (2018/04/02)
The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R1, R2, R3, and R4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.
Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3·OEt2 is a better catalyst than TMSOTf
Li, Yali,Mo, Huaping,Lian, Gaoyan,Yu, Biao
, p. 14 - 22 (2013/01/15)
With BF3·OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (a higher temperature. BF 3·OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the α/β-O-glycosides and side-products.
Synthesis of oligomeric 4-(glycosyloxy)benzoate macrocyclic glycosides
Li, Yali,Sun, Jiansong,Gong, Yanqing,Yu, Biao
scheme or table, p. 3654 - 3663 (2011/06/24)
Clemoarmanoside A and Clemahexapetoside A, two novel cyclic dimers of 4-(glycosyloxy)benzoates containing the unusual d-allopyranose as one of the sugar units, were synthesized for the first time. The convenient synthetic approach was adapted to the assembly of the symmetrical trimeric, tetrameric, and pentameric congeners. The synthesis clarified the discrepancy in the NMR data reported for the natural products. X-ray diffraction analysis of Clemahexapetoside A revealed that it adopted an armchair conformation with two carbohydrate rings as the arms and two aromatic rings as the back and seat, respectively.
Total synthesis of macrocyclic glycosides, clemochinenosides A and B, and berchemolide, by fluorous mixture synthesis
Kojima, Masaru,Nakamura, Yutaka,Ito, Shun,Takeuchi, Seiji
experimental part, p. 6143 - 6149 (2010/02/27)
The total synthesis of clemochinenoside A and the first total syntheses of clemochinenoside B and berchemolide were achieved simultaneously via macrocyclization of 4-O-(4-O-F13benzyl-β-d-glucopyranosyl)syringic acid with 4-O-(4-O-F17
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.
Berchemolide, a novel dimeric vanillic acid glucoside from Berchemia racemosa
Sakurai,Kobayashi,Shigihara,Inoue
, p. 851 - 853 (2007/10/02)
A new phenol glycoside named berchemolide was isolated together with (+)-catechin and (-)-epicatechin (as acetates), from the stems of Berchemia racemosa SIEB. et ZUCC. (Rhamnaceae). The structure of berchemolide, having a dimeric dilactone structure with
