494-08-6

Usage

Uses

Used in Flavor and Fragrance Industry:
Glucovanillin is used as a precursor for the production of vanillin, which is a key component in the flavor and fragrance industry. The conversion of glucovanillin to vanillin during the curing process of vanilla beans contributes to the unique and desirable aroma of vanilla, making it a valuable ingredient in the creation of various perfumes, cosmetics, and food products.
Used in Pharmaceutical Applications:
Glucovanillin may also have potential applications in the pharmaceutical industry due to its conversion to vanillin. Vanillin has been studied for its various biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. These properties could potentially be harnessed in the development of new drugs or therapies, with glucovanillin serving as a natural and sustainable source of vanillin for such purposes.
Used in Food Industry:
In the food industry, glucovanillin is used as a natural source of vanillin, which is a widely used flavoring agent. The conversion of glucovanillin to vanillin during the curing process of vanilla beans provides the characteristic taste and aroma associated with vanilla, making it an essential ingredient in the production of various food products such as ice cream, baked goods, and beverages.

InChI:InChI=1/C14H18O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-5,10-14,16-19H,6H2,1H3/t10-,11-,12+,13-,14-/m1/s1

Upstream product

• 121-33-5 vanillin 
• 57-50-1 Sucrose 
• 2280-44-6 D-Glucose 
• 133-89-1 UDP-glucose 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 18604-50-7 citrusin C 
• 4336-91-8 3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 112572-59-5 1-<4-β-Glucopyranosyl-3-methoxy>-3-<2-hydroxy-4,6-dimethoxy-phenyl>-prop-1-en-3-on 
• 117405-51-3 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside 
• 109448-46-6 4-β-D-glucopyranosyloxy-3-methoxy-benzaldehyde thiosemicarbazone 
• 50-99-7 D-glucose 
• 121-33-5 vanillin 
• 144677-85-0 4'-formyl-2'-methoxyphenyl 4,6-O-(α-amylcinnamylidene)-β-D-glucopyranoside 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 

Relevant academic research and scientific papers

Glycosylation of vanillin by amyloglucosidase in organic media

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.

Ice recrystallization inhibitor

【Challenge】Provide a small molecule ice recrystallization inhibitor with high IRI activity even in small quantities.Solution: The ice recrystallization inhibitor according to one aspect of the present invention includes a compound represented by the following chemical formula (1) as an active ingredient.【Chemical 1】 In the chemical formula (1), R1 is an alkyl group or hydrogen, R2 is an unsaturated hydrocarbon group or acyl group, and R3 is a monosaccharide or polysaccharide.【Selection Figure】Figure 2

Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme

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.

Method for synthesizing aromatic aldehyde through iron catalyzed oxidation allyl aromatic compound

The invention discloses a method for synthesizing aromatic aldehyde through an iron catalyzed oxidation allyl aromatic compound. According to the specific method, under the promotion effect of hydrogen silane, with air or oxygen as the oxidant, the aromatic aldehyde compound is synthesized through the iron catalyzed oxidation allyl aromatic compound, the reaction temperature is 20-150 DEG C, and the time is 0.25-60 h. The method has the advantages that a catalyst source is wide, the price is low and the environment is protected; an oxidant source is wide, the price is low and no waste is generated; the reaction conditions are mild, selectivity is high and the yield is high; a substrate source is wide and stable; a substrate functional group is high in compatibility and a substrate is widein application range; complicated small molecules are compatible and can be well converted into aldehyde. The target product separation yield can reach up to 96% under the optimized reaction conditions.

Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D

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.

Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2-cis glycopyranosides is reported, as exemplified by aryl α-d-galacto-, α-d-gluco- and 2-azido α-d-glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.

Glycosylation of vanillin and 8-nordihydrocapsaicin by cultured Eucalyptus perriniana cells

Glycosylation of vanilloids such as vanillin and 8-nordihydrocapsaicin by cultured plant cells of Eucalyptus perriniana was studied. Vanillin was converted into vanillin 4-O-γ-D-glucopyranoside, vanillyl alcohol, and 4-O-γ-D-glucopyranosylvanillyl alcohol

Molecular interactions between Barley and Oat β-glucans and phenolic derivatives

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.

Substrate specificities of family 1 UGTs gained by domain swapping

Family 1 glycosyltransferases are a group of enzymes known to embrace a large range of different substrates. This study devises a method to enhance the range of substrates even further by combining domains from different glycosyltransferases to gain impro

Glycosides and?amino acyl esters of?carbohydrates as?potent inhibitors of?angiotensin converting enzyme

About 12 glycosides prepared through amyloglucosidase catalysis and 23 amino acyl esters of carbohydrates prepared through lipase catalysis in organic solvents showed angiotensin converting enzyme (ACE) inhibition activity. Both amino acyl esters of carbohydrates and glycosides exhibited IC50 values for ACE inhibition in the 0.5?mM to 15.7?mM range. Eugenyl-d-glucoside (IC50: 0.5 ± 0.04?mM), l-isoleucyl-d-glucose (IC50: 0.7 ± 0.067?mM), vanillyl-d-sorbitol (IC50: 0.8 ± 0.09?mM), l-histidyl-d-fructose (IC50: 0.9 ± 0.087?mM), l-tryptophanyl-d-fructose (IC50: 0.9 ± 0.092?mM), octyl-d-glucoside (IC50: 1.0 ± 0.093?mM), vanillyl-d-mannoside (IC50: 1.0 ± 0.089?mM), l-valyl-d-mannitol (IC50: 1.0 ± 0.092?mM) and l-phenylalanyl-d-glucose (IC50: 1.0 ± 0.089?mM) were the compounds, which showed the best ACE inhibitory activities.