147218-57-3

Basic information

• Product Name: (3beta)-30-hydroxy-11,30-dioxoolean-12-en-3-yl beta-D-glucopyranosiduronic acid
• CAS NO: 147218-57-3
• Molecular Formula: C₃₆H₅₄O₁₀
• Molecular Weight: 646.808
• Mol File: 147218-57-3.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 785°C at 760 mmHg
• Flash Point: 240.7°C
• Density: 1.31g/cm³
• Vapor Pressure: 1.78E-28mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: (3beta)-30-hydroxy-11,30-dioxoolean-12-en-3-yl beta-D-glucopyranosiduronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3beta)-30-hydroxy-11,30-dioxoolean-12-en-3-yl beta-D-glucopyranosiduronic acid(147218-57-3)
• EPA Substance Registry System: (3beta)-30-hydroxy-11,30-dioxoolean-12-en-3-yl beta-D-glucopyranosiduronic acid(147218-57-3)

Safety Data

• Hazardous Substances Data: 147218-57-3(Hazardous Substances Data)

Upstream product

• 1477-44-7 methyl glycyrrhetinate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 1405-86-3 glycyrrhizin 
• 34096-83-8 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid 
• 533934-74-6 (2S,3S,4S,5R,6R)-1-methyl-3,4,5,6-tetra-hydroxy-tetrahydro-2H-pyran-methylester 
• 150608-11-0 methyl 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranuronate 
• 127291-00-3 benzyl 3β-(glucuron-1'β-yl)-glycyrrhetate 
• 51984-75-9 benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate 
• 169557-99-7 2,3,4-tri-O-benzoyl-1-deoxy-1-(2,2,2-trichloro-1-iminoethoxy)-α-D-glucopyranuronate, methyl ester 
• 1173698-23-1 3-O-(methyl β-D-glucopyranosyluronate)-18β-glycyrrhetinic acid 
• 471-53-4 enoxolone 
• 121709-66-8 apioglycyrrhizin 
• 67-56-1 methanol 
• 27821-74-5 methyl 1-(18β-glycyrrhet-3-yl)-2',3',4'-tri-O-acetyl-β-D-glucopyranuronate 

Downstream Products

• 1449-05-4 18-α-glycyrrhetinic acid 

Relevant articles and documents

Microbial production of glycyrrhetic acid 3-O-mono-beta-D-glucuronide from glycyrrhizin by Cryptococcus magnus MG-27

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Synthesis, molecular docking and biological evaluation of Glycyrrhizin analogs as anticancer agents targeting EGFR

Glycyrrhizin (GA) analogs in the form of 3-glucuronides and 18-epimers were synthesized and their anticancer activities were evaluated. Alkaline isomerization of monoglucuronides is reported. In vitro and in vivo studies showed that glycyrrhetinic acid monoglucuronides (GAMGs) displayed higher anticancer activities than those of bisglucuronide GA analogs, while anticancer activity of the 18α-epimer was superior to that of the 18βepimer. 18α-GAMG was firstly nicely bound to epidermal growth factor receptor (EGFR) via six hydrogen bonds and one charge interaction, and the docking calculation proved the correlation between anticancer activities and EGFR inhibitory activities. Highly active 18α-GAMG is thus of interest for the further studies as a potential anticancer agent.

The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3-O-mono-β-d-glucuronide in subcritical water

To improve the bioactivity and sweetness properties of glycyrrhizic acid (GL), the hydrothermal hydrolysis of GL into glycyrrhetinic acid (GA) and glycyrrhetinic acid 3-O-mono-β-d-glucuronide (GAMG) in subcritical water was investigated. The effects of temperature, time and their interaction on the conversion ratios were analyzed and the reactions were elaborated with kinetics and thermodynamics. The results showed that GL hydrothermal hydrolysis was significantly (P 0.05) affected by reaction time and temperature, as well as their interaction, and could be fitted into first-order kinetics. The thermodynamic analysis indicated that the hydrolysis of GL was endergonic and non-spontaneous. The hydrolytic pathways were composed of complex consecutive and parallel reactions. It was concluded that subcritical water may be a potential medium for producing GAMG and GA.

TRITERPENE GLUCURONIDES AND THEIR USE AS FLAVOR MODIFIERS

The present disclosure generally provides triterpene glucuronides, and the use of such compounds and related compounds as flavor modifiers. In some aspects, the disclosure provides certain compositions that include such triterpene glucuronides, such as compositions that include such triterpene glucuronides and one or more other sweeteners. In some other aspects, the disclosure provides methods of reducing the caloric content of a sweetened article, such as a sweetened food or beverage product.

18α-Glycyrrhetinic acid monoglucuronide as an anti-inflammatory agent through suppression of the NF-κB and MAPK signaling pathway

Based on the SAR analysis of glycyrrhizin, 18α-glycyrrhetinic acid monoglucuronide (18α-GAMG) with strong inhibition against LPS-induced NO and IL-6 production in RAW264.7 cells was discovered. Western blotting and immunofluorescence results showed that 18α-GAMG reduced the expression of iNOS, COX-2, and MAPKs, as well as activation of NF-κB in the LPS-stimulated RAW264.7 cells. Further in vivo results showed that 18α-GAMG could significantly improve the pathological changes of CCl4-induced hepatic fibrosis.