113349-27-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside is used as a bioactive compound for its potential therapeutic properties. It is being investigated for its possible use in the development of new drugs due to its pharmacological activities.
Used in Nutraceutical Industry:
In the nutraceutical industry, 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside is used as a natural ingredient for its potential health benefits. It may be incorporated into dietary supplements and functional foods for its possible positive effects on human health.
Used in Cosmetic Industry:
3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside is used as an active ingredient in the cosmetic industry for its potential skin care benefits. It may be utilized in the development of skincare products aimed at improving skin health and appearance.
Used in Citrus Research:
3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside is used as a subject of study in citrus research for its potential as an antihypertensive agent. It is being investigated for its possible role in the development of new treatments for high blood pressure.

Upstream product

• 69017-41-0 (E)-3-(4-acetoxy-3-methoxyphenyl)-2-propen-1-ol 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 13265-84-4 D-glucal 
• 163982-16-9 (1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate) 
• 149198-97-0 3,4,6-tri-O-pivaloyl-D-glucal 
• 182344-21-4 (4-hydroxy-3-methoxyphenyl)boronic acid 
• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 7368-78-7 4-bromoguaiacol 
• 50-99-7 D-glucose 
• 2595-07-5 allyl β-D-glucopyranoside 
• 864757-97-1 2-(4-bromo-2-methoxyphenoxy)tetrahydropyran 
• 869728-94-9 4-hydroxy-3-methoxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 37791-78-9 (2E)-3-(4-O-acetyl-3-methoxyphenyl)prop-2-en-1-yl acetate 
• 458-35-5 coniferal alcohol 

Relevant academic research and scientific papers

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

A selective and mild glycosylation method of natural phenolic alcohols

Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

Simple preparation of phenylpropenoid β-D-glucopyranoside congeners by Mizoroki-Heck type reaction using organoboron reagents

Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (3) and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranosides (4a-m) in good yield. Among them, coupling products 4a-m were converted to not only the naturally occurring phenylpropenoid β-d-glucopyranoside analogues (1a-e) but also the unnaturally ones (1f-m).

Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose

1,2-Anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford β-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present resection.