34096-83-8

Basic information

• Product Name: GLYCYRRHETIC ACID 3-O-GLUCURONIDE
• Synonyms: GLYCYRRHETIC ACID 3-O-GLUCURONIDE;glycyrrhetyl 3-monoglucuronide;[(18β)-20β-Carboxy-11-oxo-30-norolean-12-en-3β-yl]β-D-glucopyranosiduronic acid;3-O-β-D-Glucuronopyranosyl-18β-glycyrrhetinic acid;3β-(β-D-Glucurono pyranosyloxy)-11-oxooleana-12-ene-30-oic acid;GAMG;Glycyrrhetic Acid 3-O-β-D-Glucuronide;(3β,20β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl
• CAS NO: 34096-83-8
• Molecular Formula: C₃₆H₅₄O₁₀
• Molecular Weight: 646.81
• Product Categories: Sugars, Carbohydrates & Glucosides;Chiral Reagents;Glucuronide;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents, Glucuronide, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 34096-83-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 785°Cat760mmHg
• Flash Point: 240.7°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 1.78E-28mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.82±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: GLYCYRRHETIC ACID 3-O-GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GLYCYRRHETIC ACID 3-O-GLUCURONIDE(34096-83-8)
• EPA Substance Registry System: GLYCYRRHETIC ACID 3-O-GLUCURONIDE(34096-83-8)

Safety Data

• Hazardous Substances Data: 34096-83-8(Hazardous Substances Data)

Usage

Uses

A metabolite of Glycyrrhetic acid, an anti-inflammatory (topical).

InChI:InChI=1/C36H54O10/c1-31(2)21-8-11-36(7)27(34(21,5)10-9-22(31)45-29-25(40)23(38)24(39)26(46-29)28(41)42)20(37)16-18-19-17-33(4,30(43)44)13-12-32(19,3)14-15-35(18,36)6/h16,19,21-27,29,38-40H,8-15,17H2,1-7H3,(H,41,42)(H,43,44)/t19-,21-,22-,23-,24-,25+,26-,27+,29+,32+,33-,34-,35+,36+/m0/s1

Upstream product

• 1405-86-3 glycyrrhizin 
• 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 
• 1477-44-7 methyl glycyrrhetinate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 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

• 147218-57-3 glycyrrhetic acid 3-O-mono-β-D-glucuronide 
• 471-53-4 enoxolone 

Relevant articles and documents

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.

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.

Efficient synthesis of glycyrrhetinic acid glycoside/glucuronide derivatives using silver zeolite as promoter

3-O-Glycopyranosides of glycyrrhetinic acid have been synthesized in good to high yields and excellent stereoselectivity using glycosyl bromide donors and silver zeolite as promoter. In addition to the preparation of glycosides containing β-linked glucosy