117405-51-3

Basic information

• Product Name: 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside
• Synonyms: 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside
• CAS NO: 117405-51-3
• Molecular Weight: 356.329
• Mol File: 117405-51-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside(117405-51-3)
• EPA Substance Registry System: 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside(117405-51-3)

Safety Data

• Hazardous Substances Data: 117405-51-3(Hazardous Substances Data)

Usage

General Description

4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside, also known as dihydromyricetin-3-O-β-D-glucoside (DMG), is a natural chemical compound found in plants such as Ampelopsis grossedentata and Hovenia Dulcis. It is a type of flavonoid glycoside that possesses antioxidant, anti-inflammatory, and hepatoprotective properties. DMG has been extensively studied for its potential therapeutic effects in the treatment of liver diseases, as it has been found to inhibit the formation of free radicals and reduce oxidative stress in the liver. Additionally, DMG has been investigated for its potential use in the prevention and treatment of alcohol-induced liver damage, as it has shown promising results in animal studies. Overall, 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside has the potential to be a valuable therapeutic agent for various health conditions due to its beneficial biological activities.

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 133-89-1 diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester 
• 66642-79-3 trans-ferulic acid methyl ester 4-tetraacetylglucoside 
• 94393-06-3 4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester 
• 141-82-2 malonic acid 
• 494-08-6 glucovanillin 

Downstream Products

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 50-99-7 D-glucose 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 

Relevant articles and documents

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation

This work describes the chemical synthesis of O-aryl-β-D-glucosides and 1-O-β-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-β-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-β-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-β-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the π-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.