113349-27-2

Basic information

• Product Name: 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside
• Synonyms: (E)-Isoconiferin;[(2E)-3-(3-Methoxy-4-hydroxyphenyl)2-propenyl]β-D-glucopyranoside;[(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenyl]β-D-glucopyranoside;3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside;Citrusin D;trans-Coniferyl alchol 9-O-glucoside
• CAS NO: 113349-27-2
• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34108
• Mol File: 113349-27-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 606.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.44±0.1 g/cm3(Predicted)
• PKA: 10.02±0.31(Predicted)
• CAS DataBase Reference: 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside(113349-27-2)
• EPA Substance Registry System: 3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside(113349-27-2)

Safety Data

• Hazardous Substances Data: 113349-27-2(Hazardous Substances Data)

Usage

Description

3-Methoxy-4-hydroxycinnamyl β-D-glucopyranoside is a naturally occurring compound found in various plants, characterized by its unique chemical structure that features a hydroxycinnamyl moiety and a β-D-glucopyranoside unit. It possesses potential biological activities and has been a subject of interest for its potential applications in various fields.

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

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

Downstream Products

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

Relevant articles and documents

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.

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).