Glycyrrhetic Acid 3-O-Glucuronide

Base Information

• Chemical Name: Glycyrrhetic Acid 3-O-Glucuronide
• CAS No.: 34096-83-8
• Molecular Formula: C36H54 O10
• Molecular Weight: 646.819
• DSSTox Substance ID: DTXSID70955639
• Nikkaji Number: J396.653D
• Wikidata: Q82935324
• Mol file: 34096-83-8.mol

Synonyms:1-(18 beta-glycyrrhet-3-yl)glucopyranuronic acid;3-(monoglucuron-1'-yl)-18-glycyrrhetic acid;3-MGA;3-monoglucuronyl-glycyrrhetinic acid;3beta-D-(monoglucuronyl)-18beta-glycyrrhetinic acid;glycyrrhetic acid 3-O-beta-D-monoglucuronide;glycyrrhetic acid-3-O-glucuronide;glycyrrhetyl 3-monoglucuronide

Chemical Property of Glycyrrhetic Acid 3-O-Glucuronide

Chemical Property:

• Vapor Pressure: 1.78E-28mmHg at 25°C
• Boiling Point: 785°Cat760mmHg
• PKA: 2.82±0.70(Predicted)
• Flash Point: 240.7°C
• PSA: 170.82000
• Density: 1.31g/cm³
• LogP: 4.32910
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 646.37169792
• Heavy Atom Count: 46
• Complexity: 1340

Purity/Quality:

≥98% ^*data from raw suppliers

GlycyrrheticAcid3-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)O)C)C(=O)C=C5C3(CCC6(C5CC(CC6)(C)C(=O)O)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)C)(C)C(=O)O
• Uses: A metabolite of Glycyrrhetic acid, an anti-inflammatory (topical).

Technology Process of Glycyrrhetic Acid 3-O-Glucuronide

There total 20 articles about Glycyrrhetic Acid 3-O-Glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

β-glycyrrhizin → 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid (34096-83-8,147218-57-3)

Guidance literature:

With Pectinex Ultra SP-L; In water; at 40 ℃; for 216h;

Reference yield: 93.5%

methanol (67-56-1) + methyl 1-(18β-glycyrrhet-3-yl)-2',3',4'-tri-O-acetyl-β-D-glucopyranuronate (27821-74-5,69465-31-2) → 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid (34096-83-8,147218-57-3)

Guidance literature:

With potassium hydroxide; for 2h; Ambient temperature;

Reference yield: 91.0%

3-O-(methyl β-D-glucopyranosyluronate)-18β-glycyrrhetinic acid (1173698-23-1) → 1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid (34096-83-8,147218-57-3)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2009.04.015

upstream raw materials:

methanol

methyl 1-(18β-glycyrrhet-3-yl)-2',3',4'-tri-O-acetyl-β-D-glucopyranuronate

apioglycyrrhizin

methyl glycyrrhetinate

Downstream raw materials:

enoxolone

glycyrrhetic acid 3-O-mono-β-D-glucuronide

Refernces

• 1、 -. "Chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG)". . . Retrieved 2019/01/08.
• 2、 Yang, Yong-An,Tang, Wen-Jian,Zhang, Xin,Yuan, Ji-Wen,Liu, Xin-Hua,Zhu, Hai-Liang. "Synthesis, molecular docking and biological evaluation of Glycyrrhizin analogs as anticancer agents targeting EGFR". . p. 6368 - 6381. Retrieved 2014/06/10.