117405-51-3

Usage

Uses

Used in Pharmaceutical Industry:
4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside is used as a therapeutic agent for liver diseases due to its hepatoprotective properties. It inhibits the formation of free radicals and reduces oxidative stress in the liver, offering potential benefits in the treatment of liver conditions.
Used in Preventive Medicine:
4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside is used as a preventive agent against alcohol-induced liver damage. Its antioxidant and anti-inflammatory properties have shown promising results in animal studies, suggesting its potential to protect the liver from alcohol-related damage.
Used in Nutraceutical Industry:
4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside can be used as a nutraceutical ingredient in dietary supplements and functional foods. Its antioxidant properties may contribute to overall health and well-being by combating oxidative stress and supporting the immune system.
Used in Cosmetic Industry:
4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside may be used in cosmetic products for its antioxidant and anti-inflammatory properties. It could potentially be incorporated into skincare formulations to protect the skin from environmental stressors and promote a healthy complexion.

Upstream product

• 141-82-2 malonic acid 
• 494-08-6 glucovanillin 
• 94393-06-3 4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester 
• 66642-79-3 trans-ferulic acid methyl ester 4-tetraacetylglucoside 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

Preparation method of glucoside and derivatives thereof

The invention discloses a preparation method of glucoside and derivatives thereof. According to the method, all hydroxyl groups on a sugar molecule structure are acetylated, a ligand containing phenolic hydroxyl groups is prepared at the same time, then boron trifluoride-diethyl ether is used as a catalyst, the two substances are condensed to obtain tetraacetylated glucoside, and finally acetyl protecting groups are removed to obtain the required glucoside. The method can selectively catalyze hemiacetal hydroxyl of monosaccharide to react with hydroxyl to obtain glucoside, and the product is single. The method is simple in production operation and low in equipment requirement, can be used for synthesizing glucoside and derivatives thereof with similar structures, is green and environment-friendly, and can be used for large-scale production.

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.

Loganin, Loganic Acid and Periclymenoside, a New Biosidic Ester Iridoid Glucoside from Lonicera periclymenum L. (Caprifoliaceae)

Loganin (1), loganic acid (2), and periclymenoside (3) have been isolated from Lonicera periclymenum L.The structure of the new compound 3 and the identity of the others have been determined by chemical transformations and interpretation of the spectral data.