117405-48-8

Basic information

• Product Name: 4-O-beta-Glucopyranosyl-cis-couMaric acid
• Synonyms: 4-O-beta-Glucopyranosyl-cis-couMaric acid;(2Z)-3-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid
• CAS NO: 117405-48-8
• Molecular Formula: C15H18O8
• Molecular Weight: 326.29862
• EINECS: -0
• Mol File: 117405-48-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 631.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.538±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 4.44±0.10(Predicted)
• CAS DataBase Reference: 4-O-beta-Glucopyranosyl-cis-couMaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-beta-Glucopyranosyl-cis-couMaric acid(117405-48-8)
• EPA Substance Registry System: 4-O-beta-Glucopyranosyl-cis-couMaric acid(117405-48-8)

Safety Data

• Hazardous Substances Data: 117405-48-8(Hazardous Substances Data)

Usage

Description

4-O-beta-Glucopyranosyl-cis-couMaric acid is a flavonol glycoside, a type of natural compound derived from plants, characterized by its unique structure that includes a glucose molecule attached to a coumaric acid molecule. 4-O-beta-Glucopyranosyl-cis-couMaric acid exhibits various biological activities and has potential applications in different fields due to its specific properties.

Uses

Used in Pharmaceutical Applications:
4-O-beta-Glucopyranosyl-cis-couMaric acid is used as an anti-inflammatory agent for its inhibitory effect on lipopolysaccharide-induced nitric oxide production. This property makes it a promising candidate for the development of new drugs targeting inflammation-related conditions.
Used in the Food Industry:
In the food industry, 4-O-beta-Glucopyranosyl-cis-couMaric acid can be used as a natural additive due to its potential health benefits and antioxidant properties. It may be incorporated into various products to enhance their nutritional value and provide additional health-promoting effects.
Used in Cosmetics:
4-O-beta-Glucopyranosyl-cis-couMaric acid can also be utilized in the cosmetics industry, where it may be employed for its antioxidant and anti-inflammatory properties. It could be used in the formulation of skincare products, contributing to their effectiveness in promoting skin health and reducing signs of inflammation or oxidative stress.

Upstream product

• 7400-08-0 p-Coumaric Acid 
• 134955-57-0 4-O-(6''-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid 
• 80396-57-2 protoplumericin 
• 66642-77-1 methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate 
• 117405-48-8 4-O-β-D-glucopyranosyl-Z-4-hydroxycinnamic acid 
• 153-18-4 rutin 
• 133-89-1 diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester 
• 4163-60-4 β-D-galactose peracetate 
• 3943-97-3 methyl p-hydroxycinnamate 
• 7400-08-0 para-coumaric acid 
• 61844-62-0 benzyl 3-(4-hydroxyphenyl)acrylate 

Downstream Products

• 554-87-0 methyl glucosyl-p-coumaroate 
• 50-99-7 D-glucose 
• 501-98-4 (Z)-p-coumaric acid 
• 7400-08-0 p-Coumaric Acid 
• 117405-49-9 E-4-O-β-D-glucopyranosyl-p-coumaric acid 

Relevant articles and documents

New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa

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BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA

The present invention relates to divalent compounds binding to LecA. The compounds are useful to block biofilm formation of Pseudomonas aeruginosa. The invention further relates to pharmaceutical compositions comprising these compounds and to therapeutic methods and uses of these compounds, in particular to therapeutic methods and uses for the treatment of Pseudomonas aeruginosa infections in a subject. The invention also relates to imaging of infections, such as biofilms produced by Pseudomonas aeruginosa, by using these divalent compounds.

Glycosidase-Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. (Figure presented.).

Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)

Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen