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

Uses

Citrusin D is isolated from Citrus unshiu and may have potential as an antihypertensive agent.

Upstream product

• 7368-78-7 4-bromoguaiacol 
• 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 
• 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 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).