528-16-5

Basic information

• Product Name: D-glucopyranuronic acid
• Synonyms: D-glucopyranuronic acid;3β,4α,5β,6α-Tetrahydroxytetrahydro-2H-pyran-2α-carboxylic acid;Einecs 208-429-7
• CAS NO: 528-16-5
• Molecular Formula: C₆H₁₀O₇
• Molecular Weight: 194.1394
• EINECS: 208-429-7
• Mol File: 528-16-5.mol
• Article Data: 145

Chemical Properties

• Melting Point: 267-269 °C (decomp)
• Boiling Point: 495.2°Cat760mmHg
• Flash Point: 211.1°C
• Appearance: /
• Density: 1.987g/cm³
• Vapor Pressure: 6.95E-12mmHg at 25°C
• Refractive Index: 1.685
• PKA: 2.87±0.70(Predicted)
• CAS DataBase Reference: D-glucopyranuronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: D-glucopyranuronic acid(528-16-5)
• EPA Substance Registry System: D-glucopyranuronic acid(528-16-5)

Safety Data

• Hazardous Substances Data: 528-16-5(Hazardous Substances Data)

Usage

General Description

D-Glucopyranuronic acid is a chemical compound that is derived from glucose and belongs to the family of uronic acids. It is a cyclic sugar acid with a six-membered ring structure and is a key component of glycosaminoglycans, which are essential for maintaining the structure and function of connective tissues in the body. D-Glucopyranuronic acid is also involved in the biosynthesis of various important biomolecules, such as glycoproteins and proteoglycans, and plays a crucial role in cell signaling and cell adhesion. D-Glucopyranuronic acid has potential applications in various fields, including pharmaceuticals, cosmetics, and biotechnology, due to its diverse biochemical properties and therapeutic potentials.

InChI:InChI=1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6?/m0/s1

Upstream product

• 5356-68-3 O¹-Isopropyl-β-D-glucopyranuronsaeure 
• 16749-73-8 4-O-(α-D-Glucopyranosyl-uronsaeure)-D-galactose 
• 29741-09-1 apigenin-7-O-β-D-glucuronide 
• 79154-52-2 sepositoside A 
• 84161-94-4 gypsogenic acid 3-O-β-D-glucuronopyranoside 
• 77521-62-1 C₄₁H₆₄O₁₃ 
• 59252-95-8 <α-L-arabinofuranosyl-(1-> 4)-β-D-glucuronopyranosyl-(1-> 3)>-3β-hydroxyolean-12-en-28-oic acid 
• 1852-50-2 estriol-16α-D-glucoronide 
• 29741-09-1 apigenin-7-glucuronic acid 
• 79466-08-3 (-)-Menthol glucuronide 
• 114127-73-0 (+)-Menthol glucuronide 

Downstream Products

• 5155-54-4 methyl (methyl α-D-galacturonopyranoside)uronate 
• 18486-38-9 methyl β-D-glucuronopyranoside methyl ester 
• 133640-39-8 methyl α,β-D-glucopyranosidurono-6,3-lactone 
• 17681-01-5 methyl β-D-glucofuranosidurono-6,3-lactone 
• 17681-01-5 methyl α-D-glucofuranosidurono-6,3-lactone 
• 18486-51-6 1-O-methyl-α-D-glucopyranuronic acid methyl ester 
• 110-00-9 furan 
• 98-01-1 furfural 
• 141-46-8 Glycolaldehyde 
• 67-64-1 acetone 
• 87-73-0 D-glucaric acid 
• 62133-77-1 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 
• 83023-73-8 (2S,3S,4S,5R,6R)-3,4,5,6-tetraacetoxytetrahydro-2H-pyran-2-carboxylic acid 
• 526-99-8 meso-galactaric acid 

Relevant articles and documents

Application of bacterial directed enzyme prodrug therapy as a targeted chemotherapy approach in a mouse model of breast cancer

Cancer is the second leading cause of death in the world. Some of the usual cancer treatments include surgery, chemotherapy, and radiotherapy. However, due to low efficacy and side effects of these treatments, novel targeted therapeutic methods are needed. One of the common drawbacks of cancer chemotherapy is off-target toxicity. In order to overcome this problem, many investigations have been conducted. One of the new targeted therapy methods known as bacterial directed enzyme-prodrug therapy (BDEPT) employs bacteria as enzyme carriers to convert a pro-drug to a drug specifically within the tumor site. In the present study, we used Escherichia coli DH5α carrying luxCDABE gene cluster and overexpressing β-glucuronidase for luminescent emission and enzyme expression, respectively. Enzyme expression can lead to the conversion of glycyrrhizic acid as a prodrug to glycyrrhetinic acid, a potent anti-cancer agent. DH5α-lux/βG was characterized and its stability was also evaluated. Bacteria colonization in the tumor site was measured by tissue homogenate preparation and colony counting method. Histopathological studies on the liver, spleen, and tumor were also conducted. According to the results, co-treatment of 4T1, a highly metastatic mouse breast cancer cell line, with GL and DH5α-lux/βG could significantly decrease the IC50 values. Moreover, increased number of bacteria could lead to a dramatic drop in IC50 value. Specific colonization of DH5α-lux/βG was observed in the tumor site compared with other tissues (p 0.0001). Moreover, the biocompatibility evaluation proved that DH5α-lux/βG had no adverse effects on normal tissues. Furthermore, concurrent usage of GL and bacteria in the treatment of induced 4T1 tumors in BALB/c mice significantly delayed tumor growth (p0.001) during 16 days of investigation. Based on these findings, BDEPT might be useful for targeted breast cancer therapy, although further investigations are required to confirm this.

A Reusable Column Method Using Glycopolymer-Functionalized Resins for Capture–Detection of Proteins and Escherichia coli

The use of glycopolymer-functionalized resins (Resin–Glc), as a solid support, in?column mode for bacterial/protein capture and quantification is explored. The Resin–Glc is synthesized?from commercially available chloromethylated polystyrene?resin and glycopolymer, and is characterized by fourier transform infrared spectroscopy, thermogravimetry, and elemental analysis. The percentage of glycopolymer functionalized on Resin–Glc is accounted to be 5 wt%. The ability of Resin–Glc to selectively capture lectin, Concanavalin A, over Peanut Agglutinin, reversibly, is demonstrated for six cycles of experiments. The bacterial sequestration study using SYBR (Synergy Brands, Inc.) Green I tagged?Escherichia coli/Staphylococcus aureus?reveals the ability of Resin–Glc to selectively capture?E. coli?over?S. aureus. The quantification of captured cells in the column is carried out by enzymatic colorimetric assay using methylumbelliferyl glucuronide?as the substrate. The?E. coli?capture studies reveal a consistent capture efficiency of 105?CFU (Colony Forming Units) g?1 over six cycles. Studies with spiked tap water samples show satisfactory results for?E. coli?cell densities ranging from 102 to 107?CFU mL?1. The method portrayed can serve as a basis for the development of a reusable solid support in capture and detection of proteins and bacteria.

A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica

In recent years, the scientific interest and particularly the economic significance of halophytic plants has been highly demanding due to the medicinal and nutraceutical potential of its bioactive compounds. A xero-halophyte Bassia indica is deemed to be